Villa Bay - Vacation Rentals in Adventure Chatham

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From US $529

         

9.8 (55 Reviews)

Cottage

Walk to private beach, central air, wifi, 3 bedrooms.

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $713

         

|

10.0 (3 Reviews)

House

Central AC Close to Beach Dog Friendly!

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $204

         

|

9.4 (126 Reviews)

House

Winstead Inn

• Air Conditioner
• Parking
• Pool

• Harwich
• Harwich Center

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From US $599

         

10.0 (11 Reviews)

House

Sea Glass Cottage Near Nantucket Sound Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $515

         

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10.0 (3 Reviews)

House

Fully Updated Home w Great Outdoor Space

• Air Conditioner
• Parking
• View

• Massachusetts
• South Chatham

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From US $1,040

         

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New

Cottage

1 Mi to Beach: Home w/Fire Pit & BBQ in Cape Cod!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• South Chatham

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From US $2,306

         

9.8 (47 Reviews)

House

Overlooking Wychmere Harbor, 400 steps to beach, town & Nantucket ferry.n

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Harwich Port

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From US $739

         

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10.0 (2 Reviews)

House

Stellar Home with Hot Tub & Movie Room

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $252

         

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9.6 (304 Reviews)

Hotel

Pleasant Bay Village Resort

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Chatham

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From US $388

         

9.6 (24 Reviews)

House

Lovely Home Minutes from Beach in Chatham!

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $523

         

10.0 (100 Reviews)

House

See the World Cup AND Enjoy a Chatham Vacation June 2026

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $2,160

         

10.0 (42 Reviews)

House

5-bedroom vacation home just 3 minutes drive to Cape Cod Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $555

         

9.6 (55 Reviews)

House

Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $384

         

10.0 (19 Reviews)

Cottage

Waterfront Chatham Retreat w/WiFi & Privacy

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $625

         

9.4 (25 Reviews)

House

1 Mi to Beach: Home w/Fire Pit & BBQ in Cape Cod!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• South Chatham

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From US $523

         

9.6 (8 Reviews)

House

The Cape Escape: Walk to Harding's Beach

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $271

         

8.0 (9 Reviews)

House

Whip-o-Will Woods: Dog-Friendly Cape Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Harwich
• Harwich Center

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From US $617

         

10.0 (6 Reviews)

House

Beachside Bliss: Dog Friendly & Breezy Stay

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• South Chatham

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From US $376

         

9.2 (28 Reviews)

Cottage

Pond Front Beach Pet Friendly AC WiFi

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Harwich

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From US $592

         

10.0 (27 Reviews)

House

Sleeps 10+/Walk To Buck's Pond Lake! Close To Beach/Golf/Restaurants

• Air Conditioner
• Parking
• TV

• Harwich
• East Harwich

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From US $342

         

10.0 (7 Reviews)

House

Beach Days Await at Harwich Getaway

• Air Conditioner
• Parking
• TV

• Harwich
• East Harwich

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From US $1,300

         

9.8 (28 Reviews)

Cottage

Avoid crowds with private lakefront beach perfect for large groups!

• Parking
• Pet Friendly
• View

• Massachusetts
• Harwich

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From US $690

         

9.6 (24 Reviews)

Condo

Sea Mist Cottage by the sea w/central AC & views

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $534

         

9.6 (19 Reviews)

House

Cape Cod Retreat: A/C, WiFi & Pet Friendly

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Harwich

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★ Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Adventure Chatham.