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Cheap Holiday Rentals and Houses in Chatham, MA
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Chatham
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Internet or Wifi (491)
Air Conditioning (470)
Grill (437)
Other outdoor space (413)
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Suitability
Kid friendly (487)
Pet friendly (168)
Wheelchair access (0)
Elder access (0)
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Holiday Rental House (462)
Condominium/Apartment (31)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (51)
Boat Available (14)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Atwood Museum
Chatham Lighthouse Beach
Marconi-rca Wireless Museum
Chatham Lighthouse
Maps of Antiquity
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493 rentals
in Chatham.
Beautiful home near Jacknife Beach and bike trail
26
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Convenient to all amenities and beaches in Chatham
160
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
Match:
Sleeps
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
107
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Fully Updated Chatham Cottage Near Hardings Beach
12
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Charming 3b/2ba House Close to Downtown/Pier/Beach
19
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Renovated cottage 1 mile to beach in Chatham!
18
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Outermost Waterfront Chatham Home w/ Wraparound Views
12
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Chatham walk to Cape Cod beach
99
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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4 Bedrooms, 2 Baths, Sleeps 8-10
68
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!
12
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 14
Match:
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Clean, Bright, and Spacious; Family Friendly!
26
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
12
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 4
Match:
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Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!
16
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
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Luxurious Home with Pool & Game Room in Cape Cod
9
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 11
Match:
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach
20
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
41
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Renovated, modern Chatham beach house with lots of cozy charm
20
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Beautiful Harwich home with private pool in great location!
11
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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Classic Cape House Walking Distance to the Beach
15
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC
10
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...
17
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
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As seen on
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
108
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Carriage House with Beautiful Water View, Steps to Beach & Main Street
12
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area
8
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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As seen on
Cozy Cape near Chatham Center
13
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
13
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.
25
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
12
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 9
Match:
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
17
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Full Renovation! Amazing Spot with Views!
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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As seen on
Chatham 3 Bedroom/2 Bath Retreat
11
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
8
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
69
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
9
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 8
Match:
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!
6
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.
29
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
11
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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Charming Downtown Chatham
34
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Chatham Getaway w/ Sunroom: Walk to Beach!
7
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
29
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Cozy one bedroom on White pond (Must bring your own linens)
10
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Close to Bike Path 1 Mile to Beaches!
15
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
79
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Luxury Chatham Town Home. Close to town & beaches!
16
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Fully Updated Home w/ Great Outdoor Space!
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.
12
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Pleasant Chatham Cape
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
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