Holiday Homes in Chatham
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493 rentals in Chatham.
Beautiful home near Jacknife Beach and bike trail
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Convenient to all amenities and beaches in Chatham
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
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Fully Updated Chatham Cottage Near Hardings Beach
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Charming 3b/2ba House Close to Downtown/Pier/Beach
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Renovated cottage 1 mile to beach in Chatham!
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Outermost Waterfront Chatham Home w/ Wraparound Views
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
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Chatham walk to Cape Cod beach
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4 Bedrooms, 2 Baths, Sleeps 8-10
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Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!
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Clean, Bright, and Spacious; Family Friendly!
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
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Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!
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Luxurious Home with Pool & Game Room in Cape Cod
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach
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SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
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Renovated, modern Chatham beach house with lots of cozy charm
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Beautiful Harwich home with private pool in great location!
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Classic Cape House Walking Distance to the Beach
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...
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Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
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Carriage House with Beautiful Water View, Steps to Beach & Main Street
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area
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Cozy Cape near Chatham Center
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PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
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Full Renovation! Amazing Spot with Views!
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Chatham 3 Bedroom/2 Bath Retreat
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
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Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
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Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!
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Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.
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BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
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Charming Downtown Chatham
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Chatham Getaway w/ Sunroom: Walk to Beach!
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Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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Cozy one bedroom on White pond (Must bring your own linens)
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Close to Bike Path 1 Mile to Beaches!
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Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
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Luxury Chatham Town Home. Close to town & beaches!
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Fully Updated Home w/ Great Outdoor Space!
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Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.
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Pleasant Chatham Cape
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Showing results 1-50 of 493
Frequently Asked Questions about Chatham
- Yes, here are some popular holiday rentals in Chatham that have a pool:
- Beautiful home near Jacknife Beach and bike trail
- Convenient to all amenities and beaches in Chatham
- Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
- Yes, here are some popular holiday rentals in Chatham that have internet access:
- Beautiful home near Jacknife Beach and bike trail
- Convenient to all amenities and beaches in Chatham
- Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
- The best pet friendly rentals in Chatham are:
- Convenient to all amenities and beaches in Chatham
- Chatham walk to Cape Cod beach
- 4 Bedrooms, 2 Baths, Sleeps 8-10
- Some of the most popular kid friendly rentals in Chatham are:
- Beautiful home near Jacknife Beach and bike trail
- Convenient to all amenities and beaches in Chatham
- Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
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