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Chatham House Rentals

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    Travellers to Chatham are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    425 Matching Rentals in ChathamView all 459 rentals
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    Spectacular Waterfront Townhome - Oyster Pond #321 / 14
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, Sleeps 9 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    South Chatham Cape Cod Vacation Rental (7129)1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Just steps away from Forest Beach this 3 bedroom, 3 bath home boasts wonderful views of Nantucket Sound from the three decks, main living area and the two upstairs bedrooms. The first floor den has a queen sleep-sofa and large flat-screen TV. The third bedroom and bathroom are located in an...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    *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, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,310 - $6,750 (Pets Considered)  Rents Saturday to Saturday during peak season SELECT WEEKS JUST REDUCED 10%! (click the rates tab for the new rates) Located in a premier Chatham Village location, this...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
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    Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting and modern comforts. Enjoy stunning views over Stage Harbor throughout the home and direct water access from the private dock (boats under 20' can be brought and tied up for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5850 per week Off-Season: $4400 per week Click for More Photos, Map, and Availability Calendar Gorgeous home, recently updated and lovingly decorated. This home features peeks of Oyster Pond from the newly enclosed screened porch, as well as...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    5 Bedrooms, Sleeps 12 Quick View
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    2018 Rental Rates (Cleaning Fee and Linen Fee Included): In-Season: $7,150 per week Off-Season: $4,650 per week Click for More Photos, Map, and Availability Calendar Fabulous home in a great location! About one mile from the village, and Oyster Pond Beach, it is also steps to deeded access to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    PROPERTY OVERVIEW Located just steps from family-friendly Ridgevale Beach, this charming 2BR/1.5BA cottage offers a quintessential Chatham vacation. The walk to the coast is short and the shops and restaurants of downtown are just a quick drive away! Spend your days at the picturesque beach...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    South Chatham Cape Cod Vacation Rental (4861)1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This beautiful, newer 4 bedroom, 3 bath custom home has an expansive deck and custom built patio area with plenty of outdoor seating, a fire pit and both gas and charcoal grills. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Chatham Village Charm Next to Chatham Light Peak summer weekly rate: $4,675 - $5,900  Just REDUCED! Rates for select open weeks lowered by 10% (see new rates in the rates tab) Rents Saturday to Saturday during peak season This 5 bedroom home offers impressive views of the Atlantic Ocean and a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    South Chatham Cape Cod Waterfront Vacation Rental (6972)1 / 15
    (3)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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This recently renovated 3 bedroom, 3 bath home is situated on a nicely landscaped lot nestled at the end of a private road just .2 miles from Pleasant Street Beach. This property has high-quality finishes and décor and a unique layout perfect for extended or multi-generational families or...
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    Chatham, Cape Cod 02659
    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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    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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    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 open dining and living rooms (new couch and chair coming for 2018) with flat screen TV, small kitchen with new stove for 2018, bathroom with shower stall, and two...
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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 9 Quick View
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    • DVD Player
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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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    3 Bedrooms, Sleeps 12 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,900 per week Off-Season: $1,700 per week Click for More Photos, Map, and Availability Calendar Beautiful home built in 2006 with an airy open floor plan and tons of living space throughout. Great central location, close to all the shops and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    169 Lime Hill Road CHATHAM This magnificent and well-appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from central air to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
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    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Waterfront Vacation Rental (1841)1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Spectacular panoramic water views from this 4 bedroom, 2 bath Chatham rental situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few homes where you can step out your door and take only a few steps to the water's edge. The living room, dining room, kitchen and a full...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2900 per week Off-Season: $1800 per week Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Spectacular rental property. This newer and very spacious 4 bedroom, 4.5 bathroom home offers plenty of space with it's soaring ceilings, spacious bedrooms and large back yard. Centrally located in a wonderful neighborhood of higher-end homes this rental includes use of the association pool and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9 Quick View
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    2018 Rental Rates (Cleaning Fee Included): FRIDAY TO FRIDAY In-Season: $4,725 per week Off-Season: $3,725 per week Click for More Photos, Map, and Availability Calendar Beautiful, new home centrally located in Chatham with upscale and lavish furnishings throughout. Simple elegance defines the home...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 9
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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. House has...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    This spacious 3 bedroom, 3 bathroom home has plenty of gathering space both inside and out. Inside you will find vaulted ceilings in the living room, a sunroom and a finished lower level with ample seating and flat screen TV. The beautifully landscaped yard, complemented with a stone patio, fire...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 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 and just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include central AC, washer, dryer,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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. Perfect for a relaxing getaway, this cottage is steps away from the sand, and is ready for your vacation! Stroll up...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $8450 per week Off-Season: $5950 per week Click for More Photos, Map, and Availability Calendar Stunning home located in Chatham's prestigious Stage Island neighborhood. Gaze out at Stage Harbor from almost every room in the house! It features a...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    61 Eliphamets Lane Chatham Cape Cod - Milhaven1 / 38
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond.   The Old Village is popular for its historic nature and architectural beauty.  Witness beautiful sunrise and sunset views as you are directly on the waterfront.  It is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chatham Village Classic, Behind Lighthouse (Pets Considered)  Peak Summer Rates: $5,300 - $5,500 Just REDUCED! Rates for select open weeks lowered by 10% (see new rates in the rates tab) Rents Saturday to Saturday during peak season This grand Chatham Village family home is located in Chatham,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, 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, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    $2,000 01/01 - 06/08 $2,400 06/09 - 06/22 $3,000 06/23 - 07/20 $3,400 07/21 - 08/24 $3,000 08/25 - 08/31 $2,400 09/01 - 09/14 $2,000 09/15 - 12/31 This recently renovated and fully updated 4 bedroom, 2 bathroom Chatham vacation rental is located in Harbor Cove...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1225 per week Weekly rentals from mid-JUNE to mid-SEPT Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 5
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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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    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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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2450 per week Off-Season: $1600 per week Click for More Photos, Map, and Availability Calendar Adorable, beach cottage on a quiet street ~ located within a walk or bike ride to Chatham's favorite, family-friendly Ridgevale Beach! Light & bright...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for a relaxing getaway, this romantic cottage is just steps from the sand, Find your pathway...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming.   Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 ac units in the main floor bedrooms and free...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1575 per week ~ FRIDAY TO FRIDAY Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    Spectacular Waterfront Townhome - Oyster Pond #251 / 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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