Chatham Vacation Rentals
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638 rentals in Chatham.
Pleasant Forest Shores cottages #4 : So. Chatham
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful home near Jacknife Beach and bike trail
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Convenient to all amenities and beaches in Chatham
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fully Updated Chatham Cottage Near Hardings Beach
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 3b/2ba House Close to Downtown/Pier/Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated cottage 1 mile to beach in Chatham!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Outermost Waterfront Chatham Home w/ Wraparound Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chatham Walk to Beach Cape Cod
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bedrooms, 2 Baths, Sleeps 8
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Chatham Cape Cod Vacation Rental (15578)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Clean, Bright, and Spacious; Family Friendly!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxurious Home with Pool & Game Room in Cape Cod
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated, modern Chatham beach house with lots of cozy charm
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Harwich home with private pool in great location!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Classic Cape House Walking Distance to the Beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chatham Cape Cod Vacation Rental (16729)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chatham Cape Cod Vacation Rental (15639)
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chatham Cape Cod Waterfront Vacation Rental (12273)
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Walk to Ridgevale Beach From Family Friendly Home
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Carriage House with Beautiful Water View, Steps to Beach & Main Street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 Star Waterfront in North Chatham with dock, fire pit, and beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Cape near Chatham Center
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Chatham Cape Cod Vacation Rental (50)
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full Renovation! Amazing Spot with Views!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chatham 3 Bedroom/2 Bath Retreat
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Chatham Cape Cod Vacation Rental (14295)
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Cape House .9Miles from the Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE- CLOSE TO DOWNTOWN CHATHAM!!!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-50 of 638
Frequently Asked Questions about Chatham
- Yes, here are some popular vacation rentals in Chatham that have a pool:
- Harwich Retreat, Private Pool, Beach nearby, Family Home
- Pleasant Forest Shores cottages #4 : So. Chatham
- Beautiful home near Jacknife Beach and bike trail
- Yes, here are some popular vacation rentals in Chatham that have internet access:
- Pleasant Forest Shores cottages #4 : So. Chatham
- Beautiful home near Jacknife Beach and bike trail
- Convenient to all amenities and beaches in Chatham
- The best pet friendly rentals in Chatham are:
- Convenient to all amenities and beaches in Chatham
- Chatham Walk to Beach Cape Cod
- 4 Bedrooms, 2 Baths, Sleeps 8
- Some of the most popular kid friendly rentals in Chatham are:
- Pleasant Forest Shores cottages #4 : So. Chatham
- Beautiful home near Jacknife Beach and bike trail
- Convenient to all amenities and beaches in Chatham
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