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Holiday Rentals in Chatham

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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom home with central air. The entire house is equipped with all new furniture in June of 2016 and a few antiques (including a coffee table made from a real ship’s wheel). The house sits at the end of a private drive with plenty of parking. This...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Spend an idyllic vacation swimming, sunbathing, and riding bikes across Cape Cod at this three-bedroom Harwich home, a secluded, family-friendly retreat with a private deck, an outdoor fireplace, and easy access to picturesque beaches and towns. This tree-lined home sits equidistant from Chatham...
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    West Chatham, Chatham 02645
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $6,525 per week Off-Season: $3,325 per week Click for More Photos, Map, and Availability Calendar Gorgeous home near picturesque Scatteree Beach in N. Chatham! The 'upside-down' floor plan features the kitchen and master bedroom on the second...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,050 per week Off-Season: $1,750 per week Click for More Photos, Map, and Availability Calendar Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike trail...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This 3.5 bedroom and 2 full bath dog-friendly vacation home in Chatham with beautiful marsh views is just a half mile from Hardings Beach and Oyster Pond River. This home offers such amenities as a washer/dryer, 3 A/C units, dishwasher, cable TV, WIFI, and a gas BBQ grill. The first bedroom,...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 25 September 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
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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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 14 Quick View
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    SPECIAL FOR OPEN JULY WEEKS! $6350 per week, including the cleaning fee 2018 Rental Rates (Cleaning Fee Included): $7850 per week, including the cleaning fee Off-Season: $3,900 per week Click for More Photos, Map, and Availability Calendar A large recently renovated 6 bedroom home located in the...
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    North Chatham, Chatham 02650
    Holiday Rental House - 6 Bedrooms, Sleeps 14
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    2 Bedrooms, Sleeps 4 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1325 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Quaint two bedroom cottage surrounded by beautiful gardens! Located in lovely North Chatham, this little...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    4 Bedrooms, Sleeps 10 Quick View
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    e2018 Rental Rates (Cleaning Fee Included): In-Season: $4450 per week Off-Season: $3150 per week Click for More Photos, Map, and Availability Calendar Great family rental home, within walking distance to the warm waters of kid-friendly Hardings Beach! There is sleeping for 10 people, including a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2825 per week Off-Season: $2025 per week Click for More Photos, Map, and Availability Calendar 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...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $4,725 per week No Off-Season Click for More Photos, Map, and Availability Calendar Walk to the water in minutes from this light and bright 4 BR home located in Harding's Shores! The location is fabulous, and the home features a large private...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,675 per week Off-Season: $975 per week Click for More Photos, Map, and Availability Calendar Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    Additional amenities: A/C Units 5 ~ Lower Level, Den, 1st flr BR, 2 upstairs BRs, Area Hardings Beach, Beach Umbrella, Bedding rm1 King w/bath2nd fl, Bedding rm2 Queen w/bath 2nd fl., Bedding rm3 Twin Set1st fl., Bedding rm4 2 Bunkbeds (4 twins)~ Lower Level, Bedding rm5 Queen PullOut ~ 1st floor,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    5 Bedrooms, Sleeps 11 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens included) Off-Season: $4400 per week (6/23 to 6/30 & 8/25 to 9/1) (linens included) Click for More Photos, Map, and Availability Calendar Gorgeous home in secluded North Chatham neighborhood. The home features hardwood...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,175 per week No Off-Season Click for More Photos, Map, and Availability Calendar Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1675 per week Off-Season: $1275 per week Click for More Photos, Map, and Availability Calendar Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make this a very comfortable spot for your...
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    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3000 per week Call About Off-Season Click for More Photos, Map, and Availability Calendar Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy,...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,400 per week Off-Season: $1,400 per week Click for More Photos, Map, and Availability Calendar Light and bright 4 BR home, in a great central location! This recently updated home is across from the school tennis courts and playing fields, and...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    Private Contemporary Cape Set on a Hilltop1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 3 weeks ago
    Had a great stay with my family. It was quiet, relaxing, very well stocked with everything we needed and conveniently located. Would highly recommend.
    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...
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    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...
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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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    There's a path to Pleasant Street Beach just down from this 3 bedroom 2 bathroom cottage. Enjoy a day at the beach and return to relax on the back deck with dining table and both gas and charcoal grills. The kitchen has been beautifully updated with stainless steel appliances. There is a very...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5,800 per week Off-Season: $4,100 per week Click for More Photos, Map, and Availability Calendar Location Location Location! This wonderful, family rental is a short walk or easy bike ride into downtown Chatham and offers swimming/sunbathing...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini splits and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floor, end unit condo. An open...
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2775 per week No Off-Season Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 5 weeks ago
    Great house—-convenient to beach and all Chatham attractions— very responsive owner— comfortably furnished and super clean— great vacation!
    Reviewed 30 September 2016
    We had a lovely weekend here while attending a family wedding. The house was comfortable and equipped with everything a family might need. The neighborhood is quiet and an...
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    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,...
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    West Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,975 per week Off-Season: $1,425 per week Click for More Photos, Map, and Availability Calendar Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,275 per week Off-Season: $1,525 per week Click for More Photos, Map, and Availability Calendar You will be sure to enjoy your time in the idyllic town of Chatham. This home is 1/2 mile from the quaint town center and Oyster Pond, and 1/4 mile...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,900 per week Click for More Photos, Map, and Availability Calendar Adorable beach cottage located less than 1/2 of a mile to the peaceful shoreline of Forest Beach and a 1/2 mile stroll to 2 great dining establishments, Pieces & The Talkative...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5,150 per week Off-Season: $4,375 per week Click for More Photos, Map, and Availability Calendar The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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 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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    3 Bedrooms, 1 Bathroom, Sleeps 6 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 - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3450 per week Off-Season: $2450 per week Click for More Photos, Map, and Availability Calendar Beautiful, clean beach home located a quick half mile to Chatham's Ridgevale Beach. Plenty of space to spread out with the open floor plan, as well...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    About this property
    Brand new custom built beauty in South Chatham with water views (linens included) Peak Summer Weekly Rates: $7,400 - $8,900 Rents Saturday to Saturday during peak season Be among the first to vacation at this wonderful custom-built home in South Chatham. Just finished in January 2017, this...
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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    CONDO NEXT TO COCKLE COVE BEACH IS JUST 0.9 MILES AWAY!1 / 17
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Reviewed 19 August 2014
    rental was everything we expected. Place was clean and in a great location. There were bikes, boogie boards and beach chairs for your use.
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    About this property
    Cockle Cove Beach is just 0.9 miles away from this light & bright Chatham Condominium located at Cockle Cove Ridge. The Chatham Village center is just 3 miles away for shopping, dining, Chatham A's baseball games, & the bandstand. The entry level of this 2 bedroom, 2 bath home features a living...
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    Location Information
    Chatham, Cape Cod 2659
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $4725 per week Off-Season: $3225 per week Click for More Photos, Map, and Availability Calendar Fantastic home within walking distance to the playground, ball field, Chatham Fish Pier and Downtown Chatham! Filled with nautical, upscale...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There are two dining areas, one in the kitchen and another off the main living room that opens to a small patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath,...
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    Location Information
    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2600 per week Off-Season: $1700 per week Click for More Photos, Map, and Availability Calendar Pet Friendly! Spacious four bedroom home in quiet neighborhood near town. Path to a small private beach on Lovers Lake too! Plenty of space in the...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, Sleeps 9 Quick View
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    • Waterfront
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,625 per week Off-Season: $2,525 per week Click for More Photos, Map, and Availability Calendar Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 9
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    5 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3725 per week Off-Season: $3225 per week Click for More Photos, Map, and Availability Calendar Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach, Band concerts, baseball games, Movies, and fish pier. Total of 5...
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    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5425 per week Off-Season: $2825 per week Click for More Photos, Map, and Availability Calendar Lovely home within walking distance to downtown Chatham and the Chatham A's games!! Experience all Chatham has to offer without ever having to drive...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    Chatham  Cape Cod Vacation Rental (11231)1 / 23
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 4 September 2016
    Very recently renovated this is a spacious property with everything we (family of four) could want. Big kitchen, diner, comfortable living room and bedrooms and lots of space...
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    About this property
    Located on the Stage Harbor ?loop', this very private, quintessential Chatham 4-acre retreat has been recently renovated and has all new furnishings and amenities. The home is surrounded by mature plantings and conservation land and has views of Stage Harbor from the second floor master bedroom....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2425 per week No Off-Season Click for More Photos, Map, and Availability Calendar Take advantage of an easy walk to Hardings Beach from this light and bright updated ranch. The kitchen has been opened up with new appliances and finishing...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8 Quick View
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,475 per week Off-Season: $1,475 per week Click for More Photos, Map, and Availability Calendar Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an association...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    Pet friendly
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    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,600 per week Off-Season: $1,600 per week Click for More Photos, Map, and Availability Calendar Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even...
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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    Smoking allowed
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,775 per week Off-Season: $1,775 per week Click for More Photos, Map, and Availability Calendar Charming year-round home, with central air conditioning, within walking distance to the warm waters of popular Ridgevale Beach! Recently updated,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): SPECIAL FOR 8/25-9/1 ~ $1775, including the cleaning! In-Season: $2375 per week Off-Season: $1575 per week Click for More Photos, Map, and Availability Calendar Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    6 Bedrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $12,400 per week Off-Season: $8,800 per week Click for More Photos, Map, and Availability Calendar This beautiful home on Shore Road is the perfect spot for your Chatham vacation! It offers beautiful furnishings and plenty of space for...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, Sleeps 14
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