We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cottages in Chatham, MA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    £0
    £294 Average
    £1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 9
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 45
    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 23
    5 of 5 bubbles (1) Excellent
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 bubbles (2) Excellent
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    • DVD Player
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Chatham Beach house... walk to Harding's Beach in Chatham. Wonderful home, great for families! Outdoor Shower, wrap-around porch with patio furniture and grill, hammock to relax, Cable TV, DVD player (family movies on site), wifi included, full kitchen, laundry, garage, plenty of parking. Just... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed 8 October 2016
    I had no idea how large my family had grown until I set out to organize a weekend in Chatham, MA. We started as a family of 3; 2 little girls and a dad. Now we're a family of 10...
    5 of 5 bubbles Reviewed 19 August 2016
    What a perfect rental! From the beginning, owner Sue was extremely helpful and responsive. The beautiful pictures on the website don't even do it justice- the house was beautiful...
    See all reviews
    1 / 19
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse off in the private outdoor shower before relaxing on the sunny patio. The Space: Create cherished family memories in our... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 7 November 2015
    Wonderful house, very nice quiet location within easy reach of beaches. House very clean with everything that we needed. Would highly recommend.
    5 of 5 bubbles Reviewed 29 September 2015
    This accommodation is very well appointed and has everything one could need. Chatham is an ideal base for exploring the whole of Cape Cod. You can walk from the property to a...
    See all reviews
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Housekeeping...
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood dock and picnic area just... View all property information
    Location Information
    Chatham, Cape Cod 02669
    1 / 41
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for... View all property information
    Location Information
    Chatham, Cape Cod 02650
    5 of 5 bubbles Reviewed 23 September 2014
    Amazing home with a great owner who was 100 percent accessible our whole trip. Huge house, our party of 10 didn't even know one another was there. Highly recommend the location...
    See all reviews
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 30
    South Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Private Garden
    • Central Heating
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • Outdoor Dining Area
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or... View all property information
    Location Information
    Chatham, Cape Cod 02633
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Patio
    • Parking
    • Wi-Fi
    • Private Garden
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't need to get in your car to vacation here! Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Balcony
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    RENOVATED very bright, beachy condo, 2bdrms/2bths. This unit comes equipped with AC, fully stocked kitchen and 2 decks to enjoy your wine/coffee. The decks overlook Little Mill Pound. This condo is located in town and the famed, kid friendly Oyster Beach & Lighthouse Beach are a 10 minute... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 48
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed 31 October 2016
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
    See all reviews
    1 / 47
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Internet Access
    • Parking
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 24
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Roll out of bed and onto the shore of one of the most beautiful beaches on Cape Cod! Hardings Beach is miles of fun, family friendly, coastline and this beautiful classic turn of the century Chatham rental house is located less than 3 minutes walk to the sand! This charming turn of the century... View all property information
    Location Information
    South Chatham, Chatham 02633
    1 / 12
    4.5 of 5 bubbles (4) Very good
    Private Room, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Outdoor Dining Area
    • Washer
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This lovingly restored Greek Victorian former bed and breakfast has 6 bedrooms and 5 full baths. Sleeps 12. Local lore has it that this property was floated over from Nantucket many years ago to its present site. Amenities include a Wolf range, granite counter tops, dishwasher, 2 cable TVs... View all property information
    Location Information
    Chatham, Cape Cod 02659
    3 of 5 bubbles Reviewed 31 August 2013
    Pros:1-Location few miles from the center of town, 2-Walking distance from forest beach (not good for swimming). 3-Accomedate large groups. Cons:1-It is an old...
    See all reviews
    1 / 24
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    #602 - Port View Home:  Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 16
    5 of 5 bubbles (1) Excellent
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Garden
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed 29 July 2016
    It was a nice little spot for my boyfriend and I to get away for the weekend. Had no issues with the facilities. Please keep in mind the cabin isn't air conditioned. There are...
    See all reviews
    1 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Air Conditioning
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 22
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    0.1 mile from a popular summer Nantucket Sound beach… can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in kitchen / deck / Weber gas... View all property information
    Location Information
    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed 11 July 2016
    We absolutely loved our stay at this charming seaside home, it feels like someones primary residence not a rental. The home is bright, open and beautifully appointed, plenty of...
    See all reviews
    Get the List
    1 / 34
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Patio
    • Balcony
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 20
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . The kitchen opens to a deck perfect for al fresco dinners watching the sunset.... View all property information
    Location Information
    Chatham, Cape Cod 02148
    5 of 5 bubbles Reviewed 22 August 2015
    This was a really beautiful home. An exciting mix of old and new, set on a lovely property, overlooking a lake. Sunrises and sunsets are breathless. Room enough for eight. State...
    5 of 5 bubbles Reviewed 8 August 2015
    Joy was a pleasure to work with. She was prompt with her communications to us. She explained everything we needed to do (having never done this before). The house was great...
    See all reviews
    1 / 36
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come stay at: Donnadune. Pet Friendly! Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Peak Summer Weekly Rates:  last week of June until the first week in September: $5,200 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home.... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 28
    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Porch
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2700-$3,400 A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, WiFi, a... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 20
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,850/week. Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 26
    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Parking
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central AC mini split, WiFi, and new furnishings. Sleeps 4. Read on to learn more about our Chatham Mass Vacation Rentals Peak Summer Weekly Rates:  last week of June until the first week in September:... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 14
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Balcony
    • Porch
    • Air Conditioning
    • Patio
    • Washer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor.... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 21 February 2017
    Great property & perfectly located. Close to beaches, shopping & restaurants. The house is very beautiful and spacious. Quick check in and check out & quiet & secluded property.
    5 of 5 bubbles Reviewed 17 February 2017
    Our family visited Chatham numerous times over the years. We stayed at Chatham Bars Inn, Wequassett Resort, and other rentals. By far, Oysterpond Townhome Unit 32 was the best...
    See all reviews
    1 / 20
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You will enjoy easy times in this 3 bedroom 2 bath Cape set on a hilltop. This very well-equipped house is at the end of a cul-de-sac and offers complete privacy, a large deck with grill, outdoor shower, and ample parking. It has a contemporary open and airy floor plan with cathedral ceilings and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    3 of 5 bubbles Reviewed 19 August 2016
    We are a family of four travelling from the UK and stayed at the property for one week in July. Chatham was a relaxing week after our whirlwind tour of Florida and New York. We...
    See all reviews
    1 / 26
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Sea Mist! Spacious Cape Cod Beach House with Central AC and WiFi. Steps to the ocean with deeded access to private beach. ​ Peak Summer Weekly Rates:  last week of June until the first week in September: $3,000-$3,200/week. Special deal $1275 off season! Relax and unwind at this 3... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 24
    South Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 20
    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St., Chatham for shopping,... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $2100 per week, with the cleaning fee ~~No Off-Season~~ Welcome!! This roomy Cape sits up on a hill located just off of Cockle Cove Road on a quiet one way drive. Just .4 mi to Cockle Cove Beach. There are three bedrooms and 2 full and one half baths. The master BR is en-suite... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Private Garden
    • Outdoor Dining Area
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Chatham cottage has a cozy, comfortable living /dining area and three bedrooms. There is a large, sunny deck with table and chairs for outdoor dining and a picnic table on the shady side of the house. The two dedicated parking spaces make for easy parking. It is a short walk to beautiful... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 7 July 2015
    This traditional yet very spacious Cape Cod cottage is perfectly situated in a quiet neighborhood on an lightly traveled road. It is a most pleasant five minute walk from the...
    See all reviews
    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Satellite TV
    • Parking
    • Grill
    • Washer
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charming house completely renovated in the perfect location - central to all that Chatham and the Cape have to offer. Enjoy the downtown Main Street, restaurants, beaches, Chatham A's baseball, outdoor concerts and the fishing pier only a short stroll away. When you return for the evening enjoy the... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,875-$3,975/week. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly.  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Privacy abounds just off Main Street and the home even overlooks a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 35
    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come Stay at: The Bluff House! Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. Peak Summer Weekly Rates:  last week of June until the first week in September:  $6,500/week. This spot is a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 23 November 2016
    Our family rented the Bluff House the last week of July and had a lovely time.As boat owners we took advantage of the mooring and dingy that comes with the house. Days were spent...
    5 of 5 bubbles Reviewed 19 September 2016
    My family has rented The Bluff House for the past ten years and we can’t imagine summer anywhere else! The rooms are airy and light, with amazing views across Oyster Pond River...
    See all reviews
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This cute 2 bedroom, 1 bath cottage is just under 1/10th of a mile from Pleasant Street Beach. Amenities include a window AC unit in the living room, cable TV (includes sports and weather), DVD player, Wi-Fi, furnished deck, gas grill and an enclosed outdoor shower. This property has a $75... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 22
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful water views of Pleasant Bay from this charming, sprawling ranch which has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. Amenities include AC (central throughout + wall unit in master queen), washer,... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 18 August 2016
    Just reading the description of this home can't do it justice! The location was perfect for us: high on a bluff overlooking the Sound, so we got lovely breezes even on the few...
    See all reviews
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Parking
    • Satellite TV
    • Waterfront
    • Grill
    • Outdoor Dining Area
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 12
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Terrace
    • DVD Player
    • Grill
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4 Bedroom, very bright, beachy home with SEPARATE guest house! This home comes equipped with AC, fully stocked kitchen and deck to enjoy your wine/coffee. Not to mention a private enclosed lawn to relax or play on. Located in the HEART OF TOWN. Walk out the driveway and you will find yourself... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $4225 per week, including the cleaning fee ~~~Off Season $3225 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will LOVE this beautiful home located in the Bailey's Path neighborhood, a lovely year round residential complex. The house is filled... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rates: $5250 per week, including the cleaning fee FRIDAY TO FRIDAY Rental. ~~ Off-Season: $2750 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Gorgeous beach house on a quiet street just steps to Ridgevale Beach! "Beachy" decor and furnishings throughout!... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 27
    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Quintessential Cape Cod 5 Bedroom Chatham Vacation Rental home with beach access.  A/C units in bedrooms and main living area.  Wifi too. Peak Summer Weekly Rates:  last week of June until the first week in September: $3500- $4,600/week. Welcome to North Chatham- Here you will find a... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 30
    South Chatham
    4 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brand new custom built beauty in South Chatham with water views (linens included) NEW Listing for 2017! (More photos to come soon!) Peak Summer Weekly Rates: $6,400 - $7,300 (Rents Saturday to Saturday during peak season) Be among the first to vacation at this wonderful custom-built home in South... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 15
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate ~ $4200 per week, including the cleaning fee ~ Off-Season ~ $2000 per week, including the cleaning fee ~ Charming, antique, 5 BR home located on Chatham's "loop", steps to the water and Stage Harbor Yacht Club. Enjoy the breathtaking views of Stage Harbor and Stage Harbor... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 30
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come Stay at: Valhalla! Paradise found on the shores of Eastward Point in Chatham! Luxury at its finest will surround you at every turn in this renovated, contemporary Cape Cod Vacation home offering central air and wireless internet. Read on to learn more about this Chatham Vacation Rental, or... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 18 August 2014
    My entire family enjoyed this house. In fact, it was my kids favorite. It was big enough where we could all have a quiet space or be together comfortably (all are adults). We...
    See all reviews
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed sets. The spacious open floor... View all property information
    Location Information
    Chatham, Cape Cod 02633