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Chatham House Rentals

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    354 Matching Rentals in ChathamView all 389 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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, town tennis 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...
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    South Chatham, Chatham 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Just a mile from downtown Chatham, this 4 bedroom, 3 bathroom rental has all the comforts of home. The master bedroom with queen bed and a second bedroom with 2 twins are located on the 1st floor. The other two bedrooms and a bathroom are located on the second floor. Amenities include central...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Heart Of Chatham Village- Beach, CBI, Main Street1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms (King Master w/ Ensuite), 3 Bathrooms, Sleeps 8 - Sofa Sleeps 2 Addl Newly renovated (Spring 2016), quaint and charming in the heart of Chatham Village Center. Enjoy the full benefit of being steps away from the hustle and bustle of Main Street in one direction, or the scenic beaches...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 8 Quick View
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    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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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 12 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $4725 per week Off-Season: $3225 per week Click for More Photos, Map, and Availability Calendar Spacious beach rental located just over 1/2 of a mile from the popular Hardings Beach in Chatham! Light and bright, it offers two master bedrooms,...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    2 Bedrooms, 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, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There is a sunken dining room off the main living room that opens to a furnished patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath, wet-bar area, two sleep-sofas...
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    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Classic old-style Cape Cod home overlooking Chatham Harbor with private stairs leading down to Lighthouse Beach. SUNDAY arrival and departure at this Classic old-style Cape summer house in a simply spectacular location. This 4 bedroom home inside the Old Village Historic District overlooks...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond. The home is surrounded by oak trees creating a very private setting. There is a spacious deck with dining table for dining alfresco. A path offers direct access to Taylor's Pond for kayaking, canoeing or...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Chatham Cape Cod Vacation Rental (30)1 / 14
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy your Chatham vacation in this 3 bedroom, 2 bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. This traditional Cape home features 2 bedrooms on the first floor and 2 bedrooms on the 2nd floor. The living room and kitchen lead to a second light and...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,675 per week Off-Season: $2,675 per week Click for More Photos, Map, and Availability Calendar Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! Freshly painted, it features new beds,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gorgeous views of Nantucket Sound, Ridgevale Beach and Bucks Creek from this charming 2 bedroom, 1 bath authentic Cape cottage. Located just steps to popular Ridgevale Beach, the only public beach with watersports rentals and a snack bar, this cottage has one bedroom with a full size bed and...
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    Chatham, Cape Cod 02669
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 12 Quick View
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    • DVD Player
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $8,900 per week Off-Season: $6,900 per week Click for More Photos, Map, and Availability Calendar Stunning home in town! Walk to everything on Main Street, as well as kid friendly Oyster Pond Beach, and the playground right across the street!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the...
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    Chatham, Cape Cod 02633
    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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    This recently renovated 4 bedroom, 2 bath house has a bright open floor plan with new furnishings throughout. This comfortable home is situated in a wonderful neighborhood with a great yard for children and is only 5/10ths of a mile from Nantucket Sound Beaches. A queen bedroom and a twin bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    FABULOUS CHATHAM LOCATION! JUST A SHORT DISTANCE TO CHATHAM VILLAGE.1 / 16
    (5)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Fabulous Chatham location! Just a short distance to Chatham's Main Street Village, Aunt Lydia's Cove, Chatham Fish Pier, Chatham Bars Inn, and more! This charming 2.5 bedroom and 1.5 bath home is in a tranquil neighborhood, only 5/10ths of a mile to Aunt Lydia's Cove for seal watching and the...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 9 Quick View
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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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    About this property
    Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo retreat. Nestled in a quiet...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't need to get in your car to vacation here! Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2375 per week No Off-Season Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. $1650 per week * $100 Handling...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3225 per week Off-Season: $2325 per week Click for More Photos, Map, and Availability Calendar Private, traditional style Cape house in the peaceful Sears Point area of Chatham. It has a lovely sun porch, a spacious living room and a lovely...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (8975)1 / 21
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great views of Nantucket Sound from this 3 bedroom, 2.5 bathroom Chatham cottage. This is a newer house with multiple furnished decks and balconies as well as a covered porch and is just a stones throw to a semi-private beach on Nantucket Sound. The master bedroom is detached from the main house,...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chatham Cape Cod Vacation Rental (102)1 / 19
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    $7,200/week Peak Season (7/21 -8/17) $6,800/week On Season (6/30 -7/20 and 8/18 - 8/31) $5,000/week Off Season (6/23 - 6/29 and 9/1 - 9/7) $4,300/week Off Season (6/16 - 6/22 and 9/8 - 9/14) $3,600/week Off Season (1/1 - 6/15 and 9/15 - 12/31) Spectacular 3+ bedroom, 3.5 bath home in one...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Chatham Cape Cod Vacation Rental (1050)1 / 16
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This tastefully furnished 3 bedroom, 3 bathroom home is situated in a lovely neighborhood in Chatham Village. It is less than a mile from the shops and restaurants on Main Street and even closer to the Chatham Fish Pier and Chatham Bars Inn. The kitchen was beautifully renovated this winter to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1550 per week ~ No Off-Season Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    North Chatham, Chatham 02650
    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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in one of the most desirable areas of Chatham, this 3 bedroom, 2 bathroom classic Cape home is just a short walk to Lighthouse Beach. The spacious first floor master bedroom with queen bed and sitting area opens up to a comfortably furnished deck in a lovely private back yard. You can...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    About this property
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Well maintained two bedroom home that sleeps 6. One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 10 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10 minutes! INSIDE THE HOUSE From a drive with parking...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    3 Bedrooms, 2 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, 2 Bathrooms, Sleeps 8
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    42 Seastrand Chatham This 5 bedroom home is ideal for two groups to spend a vacation together. Two Master bedrooms, one on the first floor and one on the second floor. Open kitchen and living area. The kitchen is gourmet with silestone counter tops. This cape boasts a magnificent great room with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 2.5 bathroom house is within walking distance to downtown Chatham with some of the best restaurants and shopping that Cape Cod has to offer. The living room offers plenty of new, comfortable seating and the kitchen, with granite countertops and stainless appliances, is fully...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    This 4 bedroom, 2 bath home, located just 3/10ths of a mile from Pleasant Street Beach on Nantucket Sound, boasts a lovely yard with mature plantings that offer both privacy and a peaceful setting, especially while enjoying the deck and the double swing in the back yard. Inside, this home has an...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (76)1 / 11
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming 1 floor cottage with 3 bedrooms and 1 full bath and peeks of Nantucket Sound. There is a large backyard and the beach is less than 500 feet away. Amenities include washer, dryer, dishwasher, cable TV (includes sports and weather), DVD player, Wi-Fi, enclosed outdoor shower, a deck and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Secure Parking
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    Awesome Location New to Flipkey & Trip Advisor! A classic, beautiful 3-bedroom home to spend a memorable Chatham vacation with your family. Located walking distance to downtown .75 miles to Chatham A’s Baseball field and town playground/tennis courts. Walk to Chatham Fish Pier and beach at...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Adorable, Sunny and Bright Vacation Home! This sweet home has been lovingly redone and is waiting for you to come and visit! Three bedrooms, an open and welcoming living space, redone kitchen, brand new deck and convenient location make this a great spot for your vacation to the Cape. All this and...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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