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Chatham Cottages

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    Travellers to Chatham are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    South Chatham Cape Cod Vacation Rental (76)1 / 11
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Cape Cod Pine Grove Cottage - 1/2 mile from beach!1 / 15
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Satellite TV
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    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes....
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    15 Bobbies Lane 430701 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    15 Bobbies Lane CHATHAM Charming and Updated Cottage in South Chatham! A/C, convenient to shopping, beaches, and golf. Only 1/2 mile to Nantucket Sound. Screened in Porch, WiFi, 1 Queen, 2 singles and 2 Queen Sofa beds. Sleeps 6. $1250 per week * $100 Handling Fee * Choice of $55 Damage...
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    South Chatham, Chatham 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopping, Cape Cod League Baseball...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Come stay at: Starfish Beach Cottage! Find your Pathway to Peace! Waterfront 3 bedroom, 2 bath vacation rental cottage is located right on the beach in Chatham, the best of Cape Cod. Peak Summer Weekly Rates:  last week of June until the first week in September: $3900-$4,600/week. Perfect for a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    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 miles to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 1 mile to Main St., Chatham for shopping,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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: $4800 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home....
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Waterfront Vacation Rental (6972)1 / 14
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    This 3 bedroom, 3 bath Chatham home has multiple decks overlooking Mill Creek, the salt marsh and Nantucket Sound. Stairs leading to the creek allow you to launch a kayak or paddleboard and paddle into Nantucket Sound right from the property. The house is only .5 mi walk or drive to Cockle Cove...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    11 JEANETTE DRIVE Just over a mile to downtown Chatham and also close to Hardings Beach and Oyster Pond! This great house is convenient to the bike trail, tennis courts and has deeded rights to a fresh water pond! With four bedrooms and two full baths, this updated home comfortably sleeps up to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (4520)1 / 18
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Spend your Cape Cod vacation sunbathing by the pool at this 3 bedroom, 2 1/2 bath Chatham vacation rental home. This home is located at the end of a cul-de-sac just 3/10ths of a mile from Pleasant Street Beach and Forest Beach on Nantucket Sound. The pool is surrounded by a spacious, grassy back...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2017 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 in Pleasant Bay is nearby at Jackknife Beach! This charming year-round home is impeccably maintained and has a finished lower...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    $7,200/week Peak Season (July 22 - August 18) $6,800/week On Season (7/1, 7/8, 7/15, 8/19 and 8/26) $5,000/week Off Season (week of June 24 and Sept 2) $4,300/week Off Season (week of June 17 and Sept 9) $3,600/week Off Season (before June 16 and after Sept 15) Spectacular 3+ bedroom, 3.5 bath home...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    2017 Rental Rate: $3165 per week, including the cleaning fee~~ ~~ Off-Season: $2215 per week, including the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Bright, spacious 3 bedroom home located in South Chatham, close to the Pleasant Street Beach. This home is a perfect set up for a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful views of Nantucket Sound abound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. There is a sun room off the living room with a full-size sleep sofa and the full bath was recently...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Waterfront
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    2017 Rental Rate: $1875 per week including the cleaning fee Off-Season: $1275 per week, including the cleaning fee You will love spending your beach vacation in this light and bright two-bedroom condo near Lighthouse Beach! Recently updated, it features new living and dining furniture, new carpet...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $3000 per week including the cleaning fee ~~ Weekly rentals from mid-JUNE to mid-SEPT Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy, light and bright decor. Finished walkout...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Enjoy staying in the heart of Chatham Village in this new, tastefully appointed 2 bedroom, 2.5 bath 1,300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. This home is only 2/10th's of a mile to Oyster...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $3625 per week, including the cleaning fee ~~~~~Off-Season: $2525 with cleaning fee included ~~~~~ Fabulous updated home located in North Chatham, convenient to town and many of Chatham's beaches! High ceilings & hardwood floors throughout and a screened in porch off of the...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer beach beyond. Located on a cul de sac near Eastward Ho! Country Club in North Chatham, the home is a classic Cape in style. Water access for kayaking in Pleasant Bay and beyond....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2017 Rental Rates ~ In Season, $1125 including cleaning fee No Off-Season Clean rental home located just 1/2 mile to Hardings Beach or Oyster River Boatyard. Fresh paint and furnishings throughout make this small yet comfortable rental a great buy! Good size living room with high ceilings make it...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    $7,900/week Peak Season (July 1 - September 1) $5,800/wk for the weeks of (6/24 and 9/2) $5,200/week Shoulder Season (6/17 and 9/9) $5,000/week Shoulder Season (6/10 and 9/16) $4,000/wk (before June 10 and after September 23) This beautiful 4 bedroom, 3 bathroom custom-built Cape-style home is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    2017 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, 4 Bathrooms, Sleeps 11 Quick View
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    Wonderful 4 bedroom, 3.5 bath rental home situated 3/10ths of a mile from Pleasant Street beach and Forest Beach on Nantucket Sound. This home offers plenty of living space with comfortable furnishings. There is a nicely furnished deck for relaxing afternoons or dinner after a day at the beach. The...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ref Additional amenities include: outdoor shower: enclosed, bedding rm2: twin day bed w/trundle ~ 1st floor, bedding rm1: queen ~ 1st floor, bedding rm4: queen ~ 2nd floor, beach umbrella, a/c units: 5: 1 in lr, and 1 in each bedroom, tub and shower: 1 ~ 2nd fl., priceclass: under $3000, lobster...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Waterfront Vacation Rental (4182)1 / 30
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond and is only 6/10ths of a mile to Cockle Cove beach by path. It is surrounded by oak trees creating a very private setting. There is a wonderful deck to lounge on, bbq on the gas grill or just take in the...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Welcome to #25 Stones Throw. This sunny end unit has everything you need for a relaxing vacation. There is a pool in the complex. There are no less that four beaches within a five minute drive. Salty's market is just down the hill, past the Truro Winery - also a great place for wine tasting. If...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location, location, location. Enjoy this classic 2 bedroom, 1 full bath Cape beach cottage less than 2/10ths of a mile to popular Ridgevale Beach. Amenities include window AC units in the queen bedroom as well as the kitchen/living room area, washer, dryer, dishwasher, cable TV (including sports...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    West Chatham Cape Cod Vacation Rental (2307)1 / 19
    (1)Excellent
    3 Bedrooms, 3 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, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2017 Rental Rate: $2175 per week, including the cleaning fee Off Season: $1475 per week, including the cleaning fee Recently updated, this cozy ranch is centrally located to all Chatham has to offer! It is filled with upscale furnishings and a cheerful Beachy decor. It offers two bedrooms and two...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh water ponds and just a short drive to Pleasant Bay! The property offers four comfortable bedrooms and two baths, sleeping up to 8. The first floor has a fully equipped kitchen, cozy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Waterfront cottage on Nantucket Sound. Enjoy the spectacular location and panoramic waterviews from this 6 bedroom, 2 bath Chatham rental cottage situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few cottages where you can step out your door and take only a few steps to...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Enjoy Chatham from this beautiful antique home! With 5 bedrooms and 3 full baths, it sleeps up to 12 very comfortably. The main house offers two level living with central air throughout. The first floor has a fully equipped kitchen, comfy living area, formal dining room, full, common bath with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This renovated antique 3 bedroom, 1 full bathroom Chatham home is located in a lovely neighborhood in Chatham Village. It is only 7/10ths of a mile to the shops and restaurants on Main Street in downtown Chatham and even closer (.25 mi) to the Chatham Fish Pier, Chatham Bars Inn and Claflin Landing...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $3075 per week including the cleaning fee ~ Off-Season Rate: $1775 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Summer rental one block from the popular Harding's Beach! This home is located in the private Harding's Shores Association, a great...
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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 9 Quick View
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    Welcome to "Keepin' it Reel" on Landing Lane in Chatham a 4 bedroom, 3 bath family friendly Cape Cod Vacation Rental Home that sleeps 9 and is Budget Friendly too! Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Enjoy this 4 bedroom, 3 bath Cape Cod...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Waterfront / pond front with Private Access right from house to Schoolhouse Pond in Chatham. This home is located with fantastic access to a beautiful freshwater pond. It has gorgeous views from the deck and living area. It is also so convenient to Chatham Village, the best village on Cape Cod....
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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 5 Quick View
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    2017 Rental Rate: $3675 per week, including the cleaning fee~~ Off-Season: $2675 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Unique Sea Captain's home with stunning waterfront views, right on the beach! Everyone's dream vacation spot in Chatham. Upscale furnishings...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Chatham Cape Cod Vacation Rental (6495)1 / 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    PRICE JUST REDUCED for week of 8/26 - 9/2...Now $2,000. This rental property boasts both a main house and fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms and 1 full bath. Amenities include central AC on the first floor and window AC units in the upstairs...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    2017 Rental Rate: $11,500 per week with the cleaning and linens included. Weekly rentals from mid-JUNE to mid-SEPT The views from this sprawling Crows Pond waterfront Cape, are incredible. You can see water from almost every window of this 4 bedroom, 5,400 square foot home with private dock. This...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 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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    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    Historic North Chatham Estate. Sleeps 20, private beach! (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $13,900 - $16,900 JUST REDUCED -- Remaining Peak Week reduced $2,000/week! Click on the rates tab for updated rates. (Rents Saturday to Saturday during peak season) Please...
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    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate ~ $3725 per week, including the cleaning fee Off Season: $2725 per week, including the cleaning fee Fabulous post and beam home walking distance to kid-friendly Hardings Beach! This spacious three-bedroom home is filled with upscale furnishings, two flat screen TV's and WIFI. There...
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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 7 Quick View
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    2017 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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