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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This quaint Cape home is located just minutes away from Harding's Beach, a beautiful and popular spot to spend the day soaking in the sun and sea. Situated along Bucks Creek Marsh and just a stone's throw from the Oyster River, this 3-bedroom home is a perfect mix of seclusion and convenience. A...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    255 Tanglewood Drive CHATHAM Just a short drive to many salt water beaches and fresh water ponds, as well as both downtown Chatham and Harwich Port, this house is convenient indeed! The backyard is fully enclosed and offers a great place to relax and grill after enjoying all the many things this...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your central courtyard accessed...
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    Chatham, Cape Cod 02633
    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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    122 CHATHAM CREST DRIVE Four bedroom three bath home located in a quiet part of Chatham. Two queen beds and 4 single beds this home sleeps 8. Outdoor shower, high speed internet, wifi and cable tv are some of the attributes of this vacation home. Three quarters of a mile from Ridgevale beach....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Chatham Cape Cod Vacation Rental (1771)1 / 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both downtown Chatham and beaches. This property is only 1/2 mile to White Pond, a large fresh water pond which is great for fishing, swimming or paddle boarding....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * $100 Handling Fee * Choice of...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rates: ~~~Pre-season (May 13-June 16) $1,200 per week ~~~IN SEASON: $1800 per week (June 17-Sept 9) ~~~Post-season (Sept 9-Oct 14th) $1,200 per week Off-season (subject to Owner's prior approval) $800 week $175 MANDATORY cleaning fee per lease Weekly rentals from mid-JUNE to mid-SEPT...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Views galore from this two bedroom one bath cottage nestled along a saltmarsh only 500 feet from the semi private association beach on Nantucket Sound. A perfect getaway for nature lovers and bird watchers. Newly renovated kitchen and interior includes granite countertops, stainless steel...
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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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    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...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $2375 including the cleaning fee Off-Season: $1575 per week including the cleaning fee Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale Beach! This comfy, spacious home features high speed Internet, fireplace, and a/c units in each...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Exquisitely Renovated Chatham Sea Captain's Home Linens included, brand new furnishings, hot tub Peak Summer Weekly Rates: $4,500-$5,500/week This immaculate newly renovated home is set close to everything in Chatham.  The property is located about a mile from the center of Chatham, and about a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $1925 per week including the cleaning fee ~~ Off Season: $1425 per week including the cleaning fee Comfortable home in a wonderful location near Chatham Village! Let the children play in the huge yard or walk the short distance to Chatham's playground. The location is a few blocks...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2018 Rental Rate: $2450 per week including the cleaning fee No Off-Season Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in kitchen overlooks the backyard gardens and walks out to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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...
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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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    2017 Rental Rate: $3275 per week, including the cleaning fee Off Season: $1475 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. This home is 1/2 mile from the quaint town center and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Enjoy your summer vacation in this charming bright, contemporary home just 1/2 of a mile to Pleasant Street and Red River Beaches. This 3 bedroom, 2 bath home was fully renovated in 2007 including bathrooms, kitchen and flooring. Enjoy furnished multi-level decks with a gas grill, nice yard and an...
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    Chatham, Cape Cod 02659
    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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    2017 Rental Rate: $2800 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2018 Rental Rate: $1550 per week, including the cleaning fee~~~NO OFF-SEASON~~~ Enjoy your Chatham summer vacation in this light and bright vacation home. Located on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most popular family beaches! Filled with bright colors and comfy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    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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    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 sports...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2018 Rental Rates: $4725 per week, including the cleaning fee Weekly rentals ONLY No Off-Season 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 fenced in back yard and enclosed outdoor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $6450 per week, including the cleaning fee This recently renovated antique farmhouse is filled with upscale furnishings and is practically in the center of town! Located on large lot, it offers a wonderful mixture of new and old. There is one bedroom on the first floor with a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    #601 - The Salty Seashell: Great Holiday Deal! Beautiful private Chatham home in great location with a deck, patio, grill & yard!  You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    WATERFRONT on Lover's Lake - CM03751 / 18
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Waterfront on Lovers Lake, 1 AC This lovely 3 bedroom, 2 bath ranch features a private, sandy beach right on Lovers Lake (one of Cape Cod's beautiful, glacier-formed kettle ponds); ideal for swimming, or bring your kayak and enjoy the serenity. This property is located down a quiet cul-de-sac in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 Rents Saturday to Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home This classic home is perched in the dunes of Chatham,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Near Chatham Village, Newly Remodeled, One Mile to Main Street Peak Summer Weekly Rates: $3,125 - $3,825 Rents Saturday to Saturday during peak season Linens Included This newly remodeled home is conveniently located under a mile from Chatham Village and set on a good sized lot in a quiet...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    CONDO IN CHATHAM! COCKLE COVE BEACH IS JUST 0.9 MILES AWAY!1 / 17
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    $975-$1250 Rates include all charges. No hidden fees! 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...
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    Chatham, Cape Cod 2659
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2018 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks and enjoy the amazing shops and restaurants. Head to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Chatham Cape Cod Vacation Rental (10327)1 / 12
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Enjoy this classic 3 bedroom, 1 full bath Cape beach cottage only 3/10ths of a mile to popular Ridgevale Beach. Amenities include washer, dryer, dishwasher, two window AC units (one in the Queen bedroom and one in the bedroom with 2 Twins), cable TV (includes sports and weather), DVD player, Wi-Fi,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    2018 Rental Rate: $4450 per week including the cleaning fee ~~ Off-Season: $3150 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great family rental home, within walking distance to the warm waters of kid-friendly Hardings Beach! There is sleeping for 10 people,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    52 PLEASANT STREET Easy access to Pleasant Street Beach! This house is close to South Chatham restaurants, Pleasant Street Beach, the Cape Cod Bike Trail and it is just a short drive to both downtown Chatham and Harwich Port. 3 bedrooms and 2 bathrooms allow for a comfortable living set up....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $4000 per week, including the cleaning fee Off Season: $2400 per week, including the cleaning fee Beautifully decorated and newly remodeled rental home, centrally located in North Chatham... just a quick car or bike ride to Chatham Center or any of Chatham's gorgeous beaches!...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This traditional two bedroom, one bathroom Cape Cod cottage is just .4 miles from popular Ridgevale Beach. This one floor cottage has an open living room and dining area with flat screen TV, small kitchen (no dishwasher), bathroom with shower stall, and two bedrooms, one with a full-size bed and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Come stay in this lovely, light, bright and open 2+ bedroom, 2.5 bath home with a deck overlooking a very private backyard with enclosed outdoor shower and charcoal grill. This rental is convenient to shopping, restaurants and beaches. Schoolhouse Pond is less than a mile away and Pleasant Street,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Enjoy your summer vacation in this charming 3+ bedroom 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches. Situated just 2/10ths of a mile to Mill Creek which is a great spot for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include washer, dryer,...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rate: $1775 per week with the cleaning fee ~~ Off Season Rate: $1050 per week with the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT This three bedroom home is a stones throw from Chatham's bike trail, so you can ride from your home all over the Cape. The Regional Middle School...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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