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Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Condo in Chatham
16620: Full Renovation! Amazing Location on Main St, Central A/C, Deck w/ Views!
16620 - A Step Above: Full Renovation! Amazing Location on Main St, Central A/C, Deck w/ Views! Our completely renovated and newly furnished condo, located directly in the center of town on Main Street in Chatham, is the perfect vacation spot for your next trip to Cape Cod. You will be a short walk away from many great restaurants, including Impudent Oyster, Chatham Squire, Bluefins Sushi & Sake Bar, and Wild Goose Tavern, as well as a variety of local shops, galleries, a movie theater, and plenty of other entertainment options. In addition to offering a central Main Street location, our condo is just a short drive from a number of desirable Chatham beaches; Lighthouse Beach and Oyster Pond Beach are each just a three minute drive away! Enter our thoughtfully-decorated second story condo to find a welcoming bright, open, and clean kitchen and living area with modern decor. Some features include new appliances, island seating, a large flat screen TV with sectional couch seating, central A/C, a washer/dryer, deck with gas grill, and two bedrooms on opposite sides of the condo, providing a level of privacy for each guest. Want to go shopping for shoes - just downstairs on the 1st floor of our condo building is the ultra-chic If The Shoe Fits boutique. Grab something new for your evening or beach outings. Such an amazing location with all the amenities you will need, in addition to being dog friendly, makes this vacation rental one that you won’t want to miss out on! Home Details: -Sleeps 4 -Single Floor (2nd story walkup) -Bedroom #1: 1 King Bed -Bedroom #2: 1 Full Bed -Central A/C -Cable TV -WiFi -Washer/Dryer -Dog Friendly (with additional fee, max = 1) -Deck -Gas Grill -Located on Main Street -Minutes to the Beach -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant
$168 per night
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Cottage in Chatham
Charming Chatham cottage: Walk to Schoolhouse Pond
This charming cottage is convenient to everything that Chatham and Cape Cod offers. It is a very short walk to the beach at Schoolhouse Pond, one-mile from ocean beaches, and a short drive to Chatham town center with restaurants and shopping. You’ll love relaxing on the private deck and backyard where you can sunbathe, read, bird watch, play with your dog and grill with the kids. The cottage is good for couples, families (with kids), with an additional charge/deposit for furry friends (pets).
$175 per night
Home in Chatham
'Maybe Tomorrow....' ~ the coziest summer home
Beautifully renovated historic farmhouse located on Main Street in Chatham. In our home, you will find historic charm combined with the modern conveniences your family will appreciate! Located on a lovely half acre of land, the house sits far back from the street, offering privacy but close proximity to downtown Chatham! In less than 3 miles, you can be downtown strolling the endless unique shops, dining in fabulous restaurants, as well as enjoy the Lighthouse and Chatham Lighthouse Beach.
$269 per night

Stay near Chatham's top sights

Photo of Chatham Bars Inn
Chatham Bars Inn97 locals recommend
Photo of Chatham Lighthouse
Chatham Lighthouse105 locals recommend
Photo of Ridgevale Beach
Ridgevale Beach21 locals recommend
Photo of Wequassett Resort and Golf Club
Wequassett Resort and Golf Club59 locals recommend
Photo of Chatham Pier Fish Market
Chatham Pier Fish Market77 locals recommend
Photo of Chatham Squire
Chatham Squire140 locals recommend

House rentals in Chatham

Home in Chatham
Tucked away in the middle of everything
$338 per night
Home in Chatham
Delightful Chatham Cottage, Cheerful and Clean
$101 per night
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Home in Chatham
Cute cottage walking distance to Ridgevale Beach
$113 per night
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Home in Chatham
Spacious studio on lovely pond in Chatham
$67 per night
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Home in Chatham
Chatham Charmer
$180 per night
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Home in Chatham
Beachfront Charmer! Newly Renovated.
$300 per night
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Private room in Chatham
Nantucket House of Chatham - Chatham Room
$108 per night
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Home in Chatham
Quaint Downtown Chatham Home
$249 per night
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Home in Chatham
Stunning Water Views, Walk to Beach, AC, Like New
$375 per night
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Home in Chatham
Walk to town + beach! 4BR, Newly renovated
$230 per night
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Home in Chatham
16650: Modern Cottage Feel, Great Chatham Location Near Beach & Downtown, Central A/C, Dog Friendly!
$150 per night
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Home in Chatham
16648: Fully Updated, Quiet St, Central A/C, Outdoor Shower, Ping Pong Table, Great Outdoor Space!
$144 per night
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Vacation rentals with pools in Chatham

Guest suite in Harwich Port
The Port - #5
$101 per night
Home in Chatham
The Barn at Hardings Beach
$611 per night
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Rental unit in Dennis Port
The Sea Salt Studio - Steps to the Beach!
$188 per night
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Condo in Harwich Port
Cape Cod Condo,Walk to Beach, near Nantucket Ferry
$146 per night
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Cottage in Sandwich
Gold Anchor Cottage - private hot tub getaway!
$137 per night
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Condo in Brewster
Lovely Cape Condo with Golf Course Views and Pool
$186 per night
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Private room in Harwich Port
The Captain's Quarters Suite - #10
$115 per night
Home in Dennis Port
Modern Private Beachside Cape Cod Cottage Rental
$300 per night
Private room in Brewster
Ocean Edge Resort One Bedroom Condo
$178 per night
Private room in North Eastham
Rugosa Guest House - Room 4
$121 per night
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Condo in Dennis Port
Cozy Studio Just Steps Away From the Beach!
$175 per night
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Cottage in Yarmouth
Cottage near the Beach on Mid-Cape
$197 per night
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Cottage rentals in Chatham

Cottage in Chatham
Secluded 1BR | W/D | Grill | Large Yard
$206 per night
Cottage in Chatham
Chit-Chat Cottage on White pond, near DT/beaches.
$250 per night
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Cottage in Chatham
Renovated Chatham Windmill! Walk to Beach/Town!
$225 per night
Cottage in Chatham
Chatham Beach Cottage 2BR + Loft Walk to the Beach
$314 per night
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Cottage in Chatham
Chatham Cottage - Quiet and Quaint - Beach-Bicycle
$120 per night
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Cottage in Chatham
Forbes, a South Chatham cottage
$127 per night
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Cottage in Chatham
Cozy Cottage
$206 per night
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Cottage in Chatham
Classic Cottage-Walk to Beach-Family Friendly
$214 per night
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Cottage in Chatham
Cape Cod Classic Cottage Near Forest Beach
$300 per night
PLUS
Cottage in Chatham
A True Chatham Cottage
$259 per night
Cottage in Dennis Port
Oceanview Cottage, Million $ View Sea Street Beach
$250 per night
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Cottage in Chatham
Modern Cottage With All Your Needs! Beach! Biking!
$257 per night

Stays in Chatham

Condo in Chatham
Chatham In-Town Pied-a-Terre. Be local.
$127 per night
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Hotel room in Chatham
East Room - Chatham Guest Rooms
$95 per night
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Hotel room in Chatham
Main Suite - Chatham Guest Rooms
$155 per night
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Condo in Chatham
DOWNTOWN Two Bedroom Condo in the heart of Chatham
$83 per night