1088+ Vacation Rentals Near Adventure Chatham |
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This City Knows - Vacation Rentals in Adventure Chatham

Central AC Close to Beach Dog Friendly! From US $645
         

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10.0 (3 Reviews)
House
Central AC Close to Beach Dog Friendly!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Walk to private beach, central air, wifi, 3 bedrooms. From US $834
         

9.8 (55 Reviews)
Cottage
Walk to private beach, central air, wifi, 3 bedrooms.
  • Air Conditioner
  • Parking
  • TV

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Winstead Inn From US $204
         

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9.4 (126 Reviews)
House
Winstead Inn
  • Air Conditioner
  • Parking
  • Pool

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Fully Updated Home w Great Outdoor Space From US $515
         

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10.0 (3 Reviews)
House
Fully Updated Home w Great Outdoor Space
  • Air Conditioner
  • Parking
  • View

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Sea Glass Cottage Near Nantucket Sound Beaches From US $640
         

10.0 (11 Reviews)
House
Sea Glass Cottage Near Nantucket Sound Beaches
  • Air Conditioner
  • Parking
  • TV

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Pleasant Bay Village Resort From US $252
         

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9.6 (304 Reviews)
Hotel
Pleasant Bay Village Resort
  • Air Conditioner
  • Parking
  • Pool

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Stellar Home with Hot Tub & Movie Room From US $739
         

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10.0 (2 Reviews)
House
Stellar Home with Hot Tub & Movie Room
  • Air Conditioner
  • Parking
  • Pet Friendly

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Overlooking Wychmere Harbor, 400 steps to beach, town & Nantucket ferry.n From US $1,607
         

9.8 (47 Reviews)
House
Overlooking Wychmere Harbor, 400 steps to beach, town & Nantucket ferry.n
  • Air Conditioner
  • Parking
  • Pet Friendly

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Chatham Tides From US $184
         

9.4 (671 Reviews)
Hotel
Chatham Tides
  • Air Conditioner
  • Parking
  • TV

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Lovely Home Minutes from Beach in Chatham! From US $403
         

9.6 (25 Reviews)
House
Lovely Home Minutes from Beach in Chatham!
  • Air Conditioner
  • Parking
  • TV

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See the World Cup AND Enjoy a Chatham Vacation June 2026 From US $494
         

10.0 (100 Reviews)
House
See the World Cup AND Enjoy a Chatham Vacation June 2026
  • Air Conditioner
  • Parking
  • TV

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Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail From US $537
         

9.6 (55 Reviews)
House
Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Chatham Retreat w/WiFi & Privacy From US $393
         

10.0 (19 Reviews)
Cottage
Waterfront Chatham Retreat w/WiFi & Privacy
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Cape Escape: Walk to Harding's Beach From US $425
         

9.6 (8 Reviews)
House
The Cape Escape: Walk to Harding's Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Whip-o-Will Woods: Dog-Friendly Cape Cottage From US $262
         

8.0 (9 Reviews)
House
Whip-o-Will Woods: Dog-Friendly Cape Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beachside Bliss: Dog Friendly & Breezy Stay From US $620
         

10.0 (6 Reviews)
House
Beachside Bliss: Dog Friendly & Breezy Stay
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pond Front Beach Pet Friendly AC WiFi From US $354
         

9.2 (28 Reviews)
Cottage
Pond Front Beach Pet Friendly AC WiFi
  • Air Conditioner
  • Parking
  • Pet Friendly

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

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Beach Days Await at Harwich Getaway From US $331
         

10.0 (7 Reviews)
House
Beach Days Await at Harwich Getaway
  • Air Conditioner
  • Parking
  • TV

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Sea Mist Cottage by the sea w/central AC & views From US $676
         

9.6 (24 Reviews)
Condo
Sea Mist Cottage by the sea w/central AC & views
  • Air Conditioner
  • Parking
  • TV

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Cape Cod Retreat: A/C, WiFi & Pet Friendly From US $540
         

9.6 (19 Reviews)
House
Cape Cod Retreat: A/C, WiFi & Pet Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Near Ponds Near Bike Trail AC Large Outdoor Space Cape Retreat From US $821
         

9.6 (4 Reviews)
House
Near Ponds Near Bike Trail AC Large Outdoor Space Cape Retreat
  • Air Conditioner
  • Parking
  • TV

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Spacious w/Basketball Court & Playground! From US $461
         

9.6 (34 Reviews)
House
Spacious w/Basketball Court & Playground!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Chatham Home Near the Bike Trail & Nantucket Sound (1524) From US $373
         

9.4 (13 Reviews)
House
Chatham Home Near the Bike Trail & Nantucket Sound (1524)
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Thiscityknows makes it easy to compare the best listings on Thiscityknows homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thiscityknows 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.

Weather in Adventure Chatham

View the weather forecast for Adventure Chatham before booking your Adventure Chatham Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Adventure Chatham, MA

Thiscityknows offers a large selection of top attractions around Adventure Chatham. Research things to do on your vacation before you visit Adventure Chatham.


Harwich Port Cape Cod National Seashore Nauset Beach Mayflower Beach West Dennis Beach Seagull Beach Cape Cod Inflatable Park Ocean Edge Golf Club Edward Gorey House Skaket Beach Chatham Fish Pier Cape Cod Beaches Chatham Lighthouse Sea Street Beach Nickerson State Park Breakwater Beach Corporation Beach Orleans Bowling Center Nauset Lighthouse Cape Cod Rail Trail

Adventure Chatham Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Adventure Chatham?

There are a lot of options in Adventure Chatham. If you plan on staying in the Adventure Chatham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Adventure Chatham:

How many vacation rentals are available in Adventure Chatham?

Currently, the total number of properties listed in 2026 is over 1088 in the Adventure Chatham area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Adventure Chatham.