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Chatham Cottages

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    South Chatham Cape Cod Waterfront Vacation Rental (1841)1 / 19
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Spectacular panoramic water views from this 4 bedroom, 2 bath Chatham rental situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few homes where you can step out your door and take only a few steps to the water's edge. The living room, dining room, kitchen and a full...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Get a true dose of nautical charm with this 1-bedroom, 1-bathroom Windmill vacation rental cottage, which sleeps 3. The perfect size and layout for a couple or small family, this Windmill offers all the necessary comforts of home and beautiful views of Oyster Pond for an unforgettable Cape Cod...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rates ~ In Season: $3675 per week, including the cleaning fee Off Season: $2675 per week, including the cleaning fee Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! Freshly painted, it features new beds, and furnishings...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Water Views & Just 500 ft. to Beach!! Enjoy your Cape Cod vacation at this 4 bedroom, 3 bath Chatham vacation rental. At this lovely home you will be just under 500 ft. from Pleasant Street beach on Nantucket Sound and enjoy gorgeous water views. This home features beautiful water views from the...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    73 Main Street, Unit #8 Charming second-story condominium apartment located right across the street from Lighthouse Beach. Views of the beach from deck off the living room. Walk across the street to Lighthouse Beach and also within walking distance to the Village. NO pets accepted. $1500 per week *...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chatham Cape Cod Vacation Rental (11708)1 / 19
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Enjoy your Cape Cod vacation in this updated, bright and airy 5 bedroom, 3 bath Chatham rental property. This home is located in a lovely setting, with a terrific deck overlooking a saltmarsh and just 4/10ths of a mile from popular Ridgevale Beach. Multiple spacious living areas with many windows...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (7129)1 / 17
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Just steps away from Forest Beach this 3 bedroom, 3 bath home boasts wonderful views of Nantucket Sound from the three decks, main living area and the two upstairs bedrooms. The first floor den has a queen sleep-sofa and large flat-screen TV. The third bedroom and bathroom are located in an...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This renovated 3 bedroom, 2 bathroom property in the Ridgevale Beach area is well equipped to make your vacation stay comfortable. The home features gleaming hardwood floors on the first floor, new carpeting on the second floor, updated bathrooms and a fully equipped kitchen. New for 2018 is an...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the water. Large windows, cathedral ceilings, soft colors, and modern conveniences make this home oh-so-inviting. Please note:...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    2018 Rental Rate: $4,725 including cleaning fee FRIDAY TO FRIDAY Rental ~~ Off Season: $3,725 including the cleaning fee Beautiful, new home centrally located in Chatham with upscale and lavish furnishings throughout. Simple elegance defines the home with Custom Hardwood, stone and tile floors...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $2775 per week, with the cleaning fee ~~No Off-Season~~ Take advantage of the quick walk to the Chatham A's Ball Field, the playground and Main Street from this pristine three bedroom ranch! There are two living spaces, great for the kids and adults to be able to spread out. A...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stunning panoramic views of Nantucket Sound from this traditional 4 bedroom, 2 full bathroom Cape beach house with direct access to a private beach. Living space abounds on the first floor with multiple sitting areas, large dining area, furnished deck as well as a covered porch. A master bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (3631)1 / 17
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Situated at the end of a cul-de-sac in a wonderful neighborhood this Chatham home has a very private backyard which abuts conservation land. This 4 bedroom, 2 bath home is also just a half-mile from Nantucket Sound Beaches. Amenities include central AC, washer, dryer, dishwasher, cable TV...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chatham  Cape Cod Waterfront Vacation Rental (9718)1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    $3,500/week Off Season (1/1 - 6/29 and 9/1 - 12/12) $5,200/week Peak Season (6/30 - 8/17) $4,900/week Shoulder Season (8/18 - 8/31) Enjoy your vacation in this private setting with a water view and only a short walk to downtown Chatham. This well appointed, light and bright, 4 bedroom, 2...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates~~$3225, including the cleaning fee Off Season~~$2725 per week including the cleaning fee Gorgeous, updated rental with tons of open living space. This is a great beach rental, within 1/2 mile to Ridgevale Beach. Terrific family neighborhood spot for kids. Light and bright...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chatham  Cape Cod Waterfront Vacation Rental (6520)1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Magnificent views of Bassing Harbor, Ryder's Cove and Pleasant Bay from this 4-bedroom, 3 bathroom waterfront home perched high on a bluff. This home boasts an expansive deck with plenty of outdoor seating for relaxing or dining alfresco and a spacious yard including a stairway leading down to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Pretty, shabby chic, sunny cottage and barn on private two acres of land down quiet country road. Brand new six person hot tub on deck, in time for fall or winter rental. The grounds are naturally landscaped, not manicured, no chemicals used. Enjoy the serenity of the undisturbed woods, open floor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Chatham Village Charm Next to Chatham Light Peak summer weekly rate: $4,675 - $5,900 Rents Saturday to Saturday during peak season This 5 bedroom home offers impressive views of the Atlantic Ocean and a short walk across the street to Lighthouse Beach.This updated home has been renovated with the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This traditional Cape Cod beach cottage is just up the hill from Pleasant Street Beach. Cute coastal décor fill the two bedrooms, one with a queen and one with two twins, as well as the living, dining and kitchen area. Amenities include a window AC unit in the living room, cable TV (includes...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2018 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    2018 Rental Rates ~ $4725 per week, including the cleaning fee Off Season Weeks, $3225 per week, including the cleaning fee Clean, bright, and spacious beach rental located just over 1/2 of a mile from the popular Hardings Beach in Chatham! Two master bedrooms, each with a king bed and...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $1575 per week, including the cleaning fee No Off-Season FRIDAY TO FRIDAY Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming and Kayaking in Pleasant Bay is right down the road at Jackknife Beach! This charming year-round home is well-maintained and has...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $1675 per week, including the cleaning fee Off-Season: $975 per week, including the cleaning fee Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating space too! Nice back deck off the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    105 Wood Carver Knoll, Chatham - ID# 106342. Spectacular waterfront home in Chatham overlooking Oyster Pond! Central Air, Wireless Internet, gourmet kitchen with espresso machine, Keurig and more. Enjoy the deck with incredible views of Oyster Pond, the church steeples of Main St, tidal marshes and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chatham  Cape Cod Waterfront Vacation Rental (10354)1 / 25
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Spectacular seaside views from almost every room in this beautiful 4 bedroom, 3 bathroom Chatham rental home which rests below the watchful gaze of Chatham Light. This Chatham rental home is ideally situated between scenic Lighthouse Beach and the edge of Monomoy National Wild Life Refuge, a beach...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1475 per week, including the cleaning fee Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an association picnic table and dock - great...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (993)1 / 17
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This brand new Chatham home is conveniently located only 6/10ths of a mile from Forest Beach. The gleaming hardwood floors and open floor plan give this home a light and airy feel and the dining area opens to a spacious furnished deck for relaxing afternoons or an alfresco dinner after a long day...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    West Chatham Cape Cod Vacation Rental (2307)1 / 19
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy your Cape Cod vacation in this tastefully decorated, comfortable home. It is located in Hardings Beach Hills, only 4/10ths of a mile from popular Harding's Beach. This 3 bedroom, 2.5 bathroom home has an updated kitchen with granite countertops and stainless steel appliances as well as...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    2018 Rental Rate: $9350 per week, including the cleaning fee Call about Off-Season! The entire family will enjoy this gorgeous, newly built 4+ BR home with a private association path down to Ridgevale Beach! The beach is close, there is a path across the street that takes you to a bridge to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    2018 Rental Rate: $1225 per week, including the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT Nicely decorated house on a quiet street near town and the Cape Cod Rail Trail. This is a very well maintained and comfortable home with the owner's original artwork throughout. Small yard in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    $2,800/week Peak Season (6/30 - 8/24) $1,500/week Shoulder Weeks (6/23 - 6/29 and 8/25 - 8/31) $1,400/week Off - Season (6/9 - 6/22 and 9/1 - 10/12) This upgraded and very well maintained 4 bedroom, 3 bath cape style home is situated on a cul-de-sac 8/10ths of a mile from Cockle Cove Beach....
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2018 Rental Rates: $4425 per week, including cleaning Off-Season: $3125 per week cleaning Weekly rentals from mid-JUNE to mid-SEPT Stunning, new home located on Oyster River with breathtaking views of the river and marsh. Enjoy your afternoons after the beach watching the birds and wildlife from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    2018 Rental Rate: $2225 per week including the cleaning fee ~~ Off-season $1525 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully landscaped, fenced-in, private...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Chatham Cape Cod Vacation Rental (4861)1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This beautiful, newer 4 bedroom, 3 bath custom home has an expansive deck and custom built patio area with plenty of outdoor seating, a fire pit and both gas and charcoal grills. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    2018 Rental Rate: $7000 plus a mandatory $300 cleaning fee for one week, and $450 cleaning fee for a two week lease ~~ Off-Season: $4000 per week, plus same cleaning fees as above. Weekly rentals from mid-JUNE to mid-SEPT Fabulous renovated Cape located in the heart of Chatham with water-views from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    About this property
    Overlooking the saltwater inlet of Bucks Creek Marsh, this stunning 3BR/3BA waterfront home affords the quintessential Cape Cod experience. Vaulted ceilings with exposed beams and intriguing artwork create a sophisticated style, while large windows provide incredible views throughout the home....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2018 Rental Rate: $2375 per week, including the cleaning fee~~ No Off-Season Centrally located, this lovely updated three bedroom home is a wonderful spot for your Chatham vacation! Only one mile from everything downtown Chatham has to offer, it is also close the Cape Cod Rail Trail, and an easy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Convenient Location, Near Riverbay in Chatham! Open floor plan living, central A/C, 3 bedrooms and 2 bathrooms are just the beginning of what this property offers. Enjoy relaxing on the deck after exploring nearby East Harwich and Chatham. $1600 per week * $100 Handling Fee * Choice of $55...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lovely renovated home with central air just steps away from Lighthouse Beach. Lovely renovated home just 5 doors down from beautiful Lighthouse Beach- you don t have to worry about parking! This home features many upgrades including central air conditioning and lovely, comfortable living spaces. So...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2018 Rental Rate: $2900 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (1798)1 / 17
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spend your vacation in this newer 2+ bedroom, 2.5 bath Chatham rental home situated on a lovely country lane only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. The master bedroom with queen bed is located on the first floor. The second floor bedroom has a queen and a twin bed and...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2018 Rental Rate: $9200 per week, including the cleaning fee Off Season: $6650 per week, including the cleaning fee Stunning home located in Chatham's prestigious Stage Island neighborhood. Gaze out at Stage Harbor from almost every room in the house! It features a contemporary design, offering a...
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    Location Information
    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Smoking allowed
    About this property
    2018 Rental Rate: $2825 per week including the cleaning fee ~~~ Off-Season: $2225 per week including the cleaning fee Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to Cow Yard Landing for enjoying the morning...
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    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Smoking allowed
    About this property
    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms all...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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