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Holiday Rentals in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday home today, and have the perfect trip.
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    3 Bedrooms, Sleeps 6 Quick View
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    South Chatham Cape Cod Vacation Rental (3388)1 / 20
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    $9,800/week Peak Season (7/27 - 8/16) $9,400/week Shoulder Season (Weeks of 7/20 and 8/17) $8,900/week Shoulder Season (Weeks of 7/13 and 8/24) $8,400/week Shoulder Season (Week of 7/6) $7,900/week Shoulder Season (Weeks of 6/29 and 8/31) $6,500/week Off Season (Week of 9/7) $6,000/week Off...
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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 7 Quick View
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    Enjoy views of Nantucket Sound from every floor of this recently updated, meticulously maintained, 3 bedroom, 2 bathroom Chatham rental property. It is a perfect balance between having all of the modern amenities, with an open, light and bright feel while still maintaining the true essence of a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to Forest Beach Cottage. This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach.   Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four bedrooms, two baths, and an outstanding family room. (Small...
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    South Chatham, Chatham 02659
    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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    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, 4 Bathrooms, Sleeps 10 Quick View
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    Immaculate Fully Renovated Chatham Village Home, Walk to Beach & Village Peak Summer Weekly Rates: $8,550-$9,500 (Linens Included) Rents Saturday to Saturday during peak season Please note these photos were taken before the renovations. Photos of the new home to be posted after the first of the...
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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 8 Quick View
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    04/27/19 - 06/08/19 $1,400 06/08/19 - 06/22/19 $2,000 06/22/19 - 06/29/19 $2,500 06/29/19 - 08/24/19 $2,900 08/24/19 - 08/31/19 $2,000 08/31/19 - 09/07/19 N/A 09/07/19 - 11/02/19 $1,400 Enjoy the convenient location of this 3 bedroom, 2 full bathroom classic Cape style Chatham...
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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 8 Quick View
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    On Season Weeks of 6/29 - 8/24 ~ $3,500/wk Shouder Week of 8/24 - 8/31 ~ $3,200 This renovated 3 bedroom, 2 bathroom property in the Ridgevale Beach area is well equipped to make your vacation stay comfortable. The home features gleaming hardwood floors on the first floor, new carpeting on the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning/Linens Fee Included): In-Season: $13,000 per week Off-Season: Call for Availability Click for More Photos, Map, and Availability Calendar Stunning four bedroom home on Holway Street, with fabulous water views from almost every room in the house! Filled with gorgeous...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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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 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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    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful views of Nantucket Sound abound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. This home boasts multiple living areas including the living room, which has recently been upgraded...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chatham Cape Cod Vacation Rental (9068)1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy this 3 bedroom, 1.5 bathroom Chatham vacation home in the Harding's Hills neighborhood only 1/2 mile from popular Harding's Beach. Exclusive rights to the Bucks Creek Association dock and picnic area for kayaking, canoeing, paddle boarding or a cookout. There is a bonus 'Florida room' with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $1425 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar 'The Cottage on the Curve' is the perfect beach get-away! This charming two bedroom cottage, with many updates, is just minutes to kayaking or...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    3 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $5575 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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    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    Historic North Chatham Estate. Sleeps 20, private beach! Linens included and new beds/furniture for 2018 Peak Summer Weekly Rates: $12,500 - $14,000 Rents Saturday to Saturday during peak season Two-night rentals available in the offseason   Please click on the 'Virtual Tour' to see a 3D tour of...
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    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    $3,700/week Peak Season (June 29 - August 30) $2,100/week for the weeks of (6/22 and 8/31) $1,800/week Shoulder Season (6/15 and 9/7) $1,600/week Shoulder Season (6/8 and 9/14) $1,400/week (before 6/8 and after 9/21) This light, bright 2 bedroom, 2 bath Chatham rental home with panoramic...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Wonderful 4 bedroom, 3.5 bath rental home situated 3/10ths of a mile from Pleasant Street Beach and Forest Beach on Nantucket Sound. This home offers plenty of living space including two living rooms separated by glass doors both with comfortable furnishings. There is a nicely furnished deck for...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, Sleeps 10 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $6300 per week Off-Season: $3300 per week Click for More Photos, Map, and Availability Calendar Gorgeous home, recently updated and lovingly decorated. Filled with upscale furnishings and stylish decor, this home offers peeks of Oyster Pond from...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    Chatham Cape Cod Vacation Rental (1936)1 / 13
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This 3 bedroom, 2 bath home is located on a cul-de-sac just over 1/2 mile to Ridgevale Beach on Nantucket Sound. There is an open and spacious back yard that is great for games and BBQs. Amenties include central AC, washer, dryer, dishwasher, Cable TV, DVD player, Wi-Fi, furnished deck, gas...
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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 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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    South Chatham Cape Cod Vacation Rental (1011)1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This lovingly cared for, 3 bedroom, 2 bathroom Chatham home with open floor plan and hardwood floors throughout is located on a cul-de-sac in a pleasant neighborhood. This home is only .5 mile from Cockle Cove Beach or .2 mile from Taylor's Pond where you can launch a kayak or paddleboard and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Fabulous Home in Chatham! Lovely and overflowing with natural light, this open floor plan home is a great home base for your vacation on the Cape! The comfortable deck offers glimpses of Oyster Pond and a great spot for relaxing after enjoying all that nearby downtown Chatham has to offer. New...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This renovated antique 3 bedroom, 1 full bathroom Chatham home is located in a lovely neighborhood in Chatham Village. It is only 7/10ths of a mile to the shops and restaurants on Main Street in downtown Chatham and even closer (.25 mi) to the Chatham Fish Pier, Chatham Bars Inn and Claflin...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2019 Rental Rate (Cleaning Fee Included): In-Season: $1750 per week No Off-Season Click for More Photos, Map, and Availability Calendar Light and bright ranch in Chatham's Countryside neighborhood. Hardwood floors throughout, on a nice quiet street. This charming ranch features central air and high...
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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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    2019 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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    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 mile to Nantucket Sound beaches and just .2 mile to Mill Creek which is great for kayaking and paddleboarding into Nantucket Sound or Taylor's Pond. Amenities include central AC, washer, dryer, dishwasher, Wi-Fi,...
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    Chatham, Cape Cod 02659
    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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    *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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    1 Bedroom, Sleeps 3 Quick View
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    Additional amenities: Area Town, Bedding rm1 King 2nd fl., Bedding rm2 Queen Sofa Bed 1st fl., Bedrooms 1.00, CD, Dist. To Downtown 1/10 mile, Distance to Beach Within 2 Blocks, Fans 1, Heat, Iron & Board, Lobster Pot, Name of beach Oyster Pond, Number of Full and Half Baths 1, Off Street Parking...
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    Chatham, Cape Cod MA
    Holiday Rental House - 1 Bedroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $8,300 per week Off-Season: $6,000 per week Click for More Photos, Map, and Availability Calendar Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the corner. The proximity to the beach is so close, you will frequent beach visits and be pleased with...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 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, flat screen TV and new half bathroom. The beautifully landscaped yard, complemented with a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 4 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: $2,700 per week Off-Season: $1,700 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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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, Sleeps 12 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,700 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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    5 Bedrooms, Sleeps 9 Quick View
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    2019 Rental Rates (Cleaning and Linen Fee Included): In-Season: $7840 per week Off-Season: $5840 per week Refundable Security Deposit - $1500 Click for More Photos, Map, and Availability Calendar This Lovely antique home overlooking the Oyster Pond Harbor has just completed a fabulous renovation!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 9
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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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    3 Bedrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,800 per week Off-Season: $1,800 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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    2 Captains Row E Chatham Cape Cod - Captain's Row1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Welcome to Captain's Row! Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court (Only 130 steps from your door!). Also...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    COMING IN 2019: BRAND NEW HEATED SALT WATER POOL! This perfectly situated Chatham rental features everything one is looking for in a Cape Cod rental. 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 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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    4 Bedrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2225 per week Off-Season: $1625 per week Click for More Photos, Map, and Availability Calendar Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully landscaped, fenced-in, private backyard....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    30 Seabeach Road Chatham Cape Cod - The Bluff House1 / 36
    (4)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    Smoking allowed
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    Come Stay at: The Bluff House! Dog Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. This spot is a boater's paradise! From kayaking to boating enthusiasts, there is a mooring available for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 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 - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $1800 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
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    Experience 'Chatham Coastal Charm'. Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Welcome to 'Keepin' it Reel' on Landing Lane in Chatham a 4 bedroom, 3 bath family friendly Cape Cod Vacation Rental Home that sleeps 9 and is Budget Friendly too! Enjoy this 4 bedroom, 3 bath Cape Cod vacation rental with central AC in Chatham. Sleeps 9. It is located in Ryder's Cove Landing...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 9 Quick View
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    Smoking allowed
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $4725 per week Off-Season: $3450 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 9
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    4 Bedrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2019 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, remodeled in 2016, located in the heart of the village and just steps to Mill Pond! It features comfortable furnishings, and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 6
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