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2026-08-20
2026-08-21
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Holiday Homes in Chatham

Oyster Beach Bungalow

37 Kent Pl, Chatham, United States Show map

Situated only 5 minutes' stroll from the Eldredge Public Library, Oyster Beach Bungalow Chatham offers quick access to numerous city landmarks nearby. More

From US$ 125 Book Now

Sea House

139 Honeysuckle Lane, Chatham, United States Show map

Situated just 8 minutes' walk from the Atwood House & Museum, Sea House Villa Chatham entices guests with fishing in the area. More

From US$ 630 Book Now

Updated Beach House Deck Outdoor Shower!

49 Florence Dr, Chatham, United States Show map

Updated Beach House Deck Outdoor Shower! Chatham villa hosts up to 6 guests and is nestled 4.6 km from natural sites such as the Cape Cod Lavender Farm. This accommodation features opportunities for… More

From US$ 678 Book Now

1 Mile From Downtown Chatham Walk To Pier

356 Old Harbor Rd, Chatham, United States Show map

The 4-bedroom 1 Mile From Downtown Chatham Walk To Pier villa is located nearly 25 minutes on foot from the Atwood House & Museum and allows guests to enjoy fishing. More

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Lucky Number Seven

Chatham, United States Show map

During the stay at Lucky Number Seven Villa Chatham, guests can indulge in fishing or visit the Chatham Village Market, located a 25-minute walk away. More

From US$ 1386 Book Now

Full Renovation Amazing Spot With Views

442 Main St, Chatham, United States Show map

Situated just a 9-minute stroll from the historic Chatham's Godfrey Windmill, the 2-bedroom Full Renovation Amazing Spot With Views Villa Chatham ensures a great leisure experience by offering… More

From US$ 782 Book Now

B By The Sea

Chatham, United States Show map

B By The Sea Villa Chatham offers swift access to various city sites, such as the Arconti American Museum, situated nearly 5 minutes' walk away. More

From US$ 246 Book Now

Large Home W Fire Pit And Dogs Welcome

21 Heatherwood Ln, Chatham, United States Show map

During the stay at Large Home W Fire Pit And Dogs Welcome Chatham, guests can indulge in fishing or visit the Chatham Marconi Maritime Center, located a 25-minute walk away. Located 4.1 km from the… More

From US$ 353 Book Now

Wrap-Around Porch Mins To Beach

2574 Main St, Chatham, United States Show map

Positioned 3.3 km from bustling shopping destinations such as the Maps of Antiquity, the 2-bedroom Wrap-Around Porch Mins To Beach Chatham villa offers guests to use a private parking lot. This… More

From US$ 382 Book Now

Walk To Beach: Chatham Gem W/ Ocean-View Sunroom!

32 Cabot Ln, Chatham, United States Show map

Located 2.9 km from the Atwood House & Museum, the 3-bedroom Walk To Beach: Chatham Gem W/ Ocean-View Sunroom! villa provides access to various tourist attractions in the vicinity. More

From US$ 416 Book Now

Pond Front Home W Game Room Dog Friendly

46 Partridge Path, Chatham, United States Show map

During the stay at Pond Front Home W Game Room Dog Friendly Chatham, guests can indulge in fishing or visit the Chatham Lighthouse, located 7 km away. Located 15 minutes' drive from the Chatham… More

From US$ 357 Book Now

Pristine Multi-Family Home W Barn Game Room

Main Street 1359, Chatham, United States Show map

The 5-bedroom Pristine Multi-Family Home W Barn Game Room Chatham is located within 5 minutes' walk of Chatham Orpheum Theatre and welcomes its guests to enjoy fishing. This Chatham villa… More

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Sun Room Beaches And Dog Welcome

40 Mayflower Dr, Chatham, United States Show map

During the stay at Sun Room Beaches And Dog Welcome Chatham villa, guests can indulge in fishing or visit the Chatham Marconi Maritime Center, located 4.4 km away. Located 10 minutes' drive from the… More

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1 Mi To Sand! Mid-Cape Chatham W/ Furnished Deck

17 Goose Pond Rd, Chatham, United States Show map

Accommodating up to 8 guests, 1 Mi To Sand! Mid-Cape Chatham W/ Furnished Deck villa is situated 4.1 km from renowned cultural sites such as the Eldredge Public Library. Providing guests with Wi-Fi… More

From US$ 712 Book Now

Centrally Located Home W Patio Fire Pit

84 Old Harbor Rd, Chatham, United States Show map

During the stay at Centrally Located Home W Patio Fire Pit Chatham, guests can indulge in fishing or visit the Atwood House & Museum, located a 17-minute walk away. Located within a 200-metre… More

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Stellar Home With Hot Tub & Movie Room

49 Bay View St, Chatham, United States Show map

Located only 350 metres from the Maps of Antiquity, the 4-bedroom Stellar Home With Hot Tub & Movie Room Chatham offers guests to relax in a Jacuzzi, or enjoy fishing. This accommodation can host up… More

From US$ 1666 Book Now

Cozy Cape Time

41 Tern Lane, Chatham, United States Show map

During the stay at Cozy Cape Time Villa Chatham, guests can indulge in horseback riding and fishing or visit the Large Lighthouse Sandy Beach, located 4.5 km away. More

From US$ 1220 Book Now

Chatham Ranch Retreat Near Hardings Beach

19 Old Cart Way, Chatham, United States Show map

Featuring horse riding tours to make your visit more entertaining, Chatham Ranch Retreat Near Hardings Beach villa is 2.9 km from the Veterans Field. Guests can enjoy windsurfing, snorkelling, and… More

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Central Ac Close To Beach Dog Friendly!

49 Monomoit Ln, Chatham, United States Show map

Situated 3.1 km from the Ridgevale Beach, the 3-bedroom Central Ac Close To Beach Dog Friendly! Chatham villa entices guests to enjoy fishing in the area. Providing guests with high-speed Internet… More

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Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-Newly Renovated Private Retreat Ac

27 Phoebe Lane, Chatham, United States Show map

During the stay at Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-Newly Renovated Private Retreat Ac villa, guests can indulge in lawn tennis, mini golf, and cycling or visit the Stage… More

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Charming Updated Home In Chatham

119 Pleasant St, Chatham, United States Show map

The 4-bedroom Charming Updated Home In Chatham accommodates up to 8 guests and offers a convenient location about a 10-minute drive from shopping venues such as the Maps of Antiquity. The Chatham… More

From US$ 350 Book Now

Ping-Pong & Backyard: Spacious Chatham Retreat

152 Stagecoach Dr, Chatham, United States Show map

Nestled 3 km from the Maps of Antiquity, Ping-Pong & Backyard: Spacious Chatham Retreat villa entices guests to explore various tourist destinations nearby. The 3-bedroom holiday home hosts up to 8… More

From US$ 417 Book Now

Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach

135 Pine Knoll Ave, Chatham, United States Show map

Hosting up to 4 guests, Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach Chatham is located in a residential area, about 4 km from the Forest Beach. Guests can enjoy canoeing at this holiday home… More

From US$ 525 Book Now

7-Br Retreat Pool, Hot Tub, Sauna, Barn

22 Lorenzo Buck Way, Chatham, United States Show map

The 7-bedroom 7-Br Retreat Pool, Hot Tub, Sauna, Barn Chatham villa can host up to 16 guests, boasting a convenient location 3.8 km from iconic cultural attractions such as the Chatham Shark Center. More

From US$ 2000 Book Now

Spacious Home With Direct Pond Access!

580 Meetinghouse Rd, Chatham, United States Show map

With the capacity to host 12 guests, Spacious Home With Direct Pond Access! Chatham is located approximately a 15-minute ride from such significant cultural landmarks as the Eldredge Public Library. More

From US$ 477 Book Now

Fully Updated Home W Great Outdoor Space

21 Quail Trl, Chatham, United States Show map

Accommodating up to 4 guests, Fully Updated Home W Great Outdoor Space Chatham is situated 4.8 km from renowned cultural sites such as the Chatham Railroad Museum. The 2-bedroom holiday home features… More

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Beautifully Renovated W Access To Beach

17 Whidah Rd, Chatham, United States Show map

The 6-bedroom Beautifully Renovated W Access To Beach Chatham villa offers proximity to nearby tourist spots, such as the Veterans Field, situated nearly 25 minutes' walk away. The accommodation… More

From US$ 1247 Book Now

Great Chatham Location Near Beach

64 Meadow Brook Rd, Chatham, United States Show map

Located around 25 minutes' walk from the Chase Park, Great Chatham Location Near Beach villa provides access to various tourist attractions in the vicinity. The accommodation can host up to 8 guests,… More

From US$ 518 Book Now

16612 - Stunning Home With Wraparound Deck Views Of Bucks Creek And Nantucket Sound

93 Ridgevale Road South, Chatham, United States Show map

Situated only 0.6 km from the Ridgevale Beach, the 2-bedroom 16612 - Stunning Home With Wraparound Deck Views Of Bucks Creek And Nantucket Sound Chatham is ideal for up to 4 guests. This villa… More

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Quintessential Cape Directly On The Cape Cod Rail Dog Friendly

Nob Hill Road 52, Chatham, United States Show map

Quintessential Cape Directly On The Cape Cod Rail Dog Friendly Villa Chatham is nestled just a 9-minute walk from the Chatham Village Market and can accommodate up to 8 guests. Located 2 km from the… More

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The Sea Star

25 Greenwood Lane, Chatham, United States Show map

Staying at The Sea Star Villa Chatham, guests can easily reach the Chatham Shark Center, located approximately 6 km away. Guests can enjoy fishing at the Chatham villa, located around a 10-minute… More

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A Chatham Pearl On Oyster River

Chatham, United States Show map

During the stay at A Chatham Pearl On Oyster River villa, guests can indulge in fishing or visit the Chatham Railroad Museum, located about 25 minutes' walk away. More

From US$ 204 Book Now

South Chatham Sunshine

Chatham, United States Show map

During the stay at South Chatham Sunshine villa, guests can indulge in fishing or visit the Cape Cod Lavender Farm, located 4.7 km away. More

From US$ 684 Book Now

Close To Bike Path 1 Mile To Beaches

39 Mayflower Dr, Chatham, United States Show map

Staying at the 3-bedroom Close To Bike Path 1 Mile To Beaches Chatham villa, guests can visit the Ridgevale Beach, which is nearly a 25-minute walk away. Suitable for up to 6 guests, the Chatham… More

From US$ 263 Book Now

Beautiful Home W Artistic Flair

5 Holly Dr, Chatham, United States Show map

The 3-bedroom Beautiful Home W Artistic Flair Chatham is located nearly a 25-minute walk from the Ridgevale Beach and provides fishing for active guests. Located 4.8 km from the Chatham Village… More

From US$ 340 Book Now

Gorgeous Home With Game Room Dog Welcome

81 Joshua Jethro, Chatham, United States Show map

Located within a 4-km distance of the family-friendly Oyster Pond Beach, the 3-bedroom Gorgeous Home With Game Room Dog Welcome Chatham provides access to various tourist attractions in the vicinity.… More

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Lovely Home Near Bike Path Dog Welcome!

193 Old Queen Anne Rd, Chatham, United States Show map

During the stay at Lovely Home Near Bike Path Dog Welcome! Chatham, guests can indulge in fishing or visit the Veterans Field, located a 20-minute walk away. Located 3.2 km from the Large Lighthouse… More

From US$ 281 Book Now

Rail Trail Access: Home 2 Mi To Lighthouse Beach!

7 Earles Way, Chatham, United States Show map

Situated 3.4 km from the Ridgevale Beach, the 3-bedroom Rail Trail Access: Home 2 Mi To Lighthouse Beach! Chatham provides access to numerous tourist attractions in the area. More

From US$ 400 Book Now

Coastal Comfort Cape Cod Charm Await

31 Bayview Street, Chatham, United States Show map

Situated 3.2 km from the Large Lighthouse Sandy Beach, Coastal Comfort Cape Cod Charm Await Chatham villa entices guests to enjoy windsurfing, hiking, and cycling in the area. Offering horse riding… More

From US$ 1135 Book Now

Spacious W Large Outdoor Area Fire Pit

125 Wood Valley Rd Ext, Chatham, United States Show map

Staying at the 4-bedroom Spacious W Large Outdoor Area Fire Pit Chatham villa, guests can visit the Wharfinger Chatham Fish Pier, which is nearly a 25-minute walk away. Offering fishing, the Chatham… More

From US$ 687 Book Now

Walk To Downtown Chatham Steps To Beach

166 Chatham Bars Avenue, Chatham, United States Show map

Staying at the 4-bedroom Walk To Downtown Chatham Steps To Beach villa, guests can easily reach the Steve Lyons Art Gallery, located a mere 500 metres away. Suitable for up to 8 guests, this Chatham… More

From US$ 1426 Book Now

Waterfront On Private Lake

404 Old Queen Anne Rd, Chatham, United States Show map

Waterfront On Private Lake Chatham villa is located 3.8 km from the Large Lighthouse Sandy Beach and provides fishing for active guests. Located 25 minutes' stroll from the Chatham Shark Center, the… More

From US$ 362 Book Now

Located On Rail Trail By Beach & Downtown

20 Wilfred Rd, Chatham, United States Show map

The 4-bedroom Located On Rail Trail By Beach & Downtown Chatham villa, located about a 5-minute walk from White Pond Beach, can host up to 8 guests. This accommodation features opportunities for… More

From US$ 495 Book Now

Game Room Walk To Nantucket Sound

47 Glendon Way, Chatham, United States Show map

During the stay at Game Room Walk To Nantucket Sound Chatham villa, guests can indulge in fishing or visit the Maps of Antiquity, located 4 km away. Located a 15-minute drive from the historic… More

From US$ 381 Book Now

Waterfront On Pond W Private Beach

909 Old Queen Anne Rd, Chatham, United States Show map

The 4-bedroom Waterfront On Pond W Private Beach Chatham villa is located 3.7 km from the Forest Beach and provides fishing for active guests. Providing guests with high-speed Internet access and… More

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Seashell Wishes-Salty Kisses

102 Morton Road, Chatham, United States Show map

Featuring horse riding tours to make your visit more entertaining, Seashell Wishes-Salty Kisses Villa Chatham is 3.8 km from the Wychmere Harbor. Guests can enjoy horseback riding and fishing at the… More

From US$ 399 Book Now

0 6 Miles To Beach Great For Families

32 E Rd, Chatham, United States Show map

During the stay at 0 6 Miles To Beach Great For Families Chatham villa, guests can indulge in fishing or visit the Red River Beach, located a 19-minute walk away. Located 4.3 km from the Cape Cod… More

From US$ 862 Book Now

Amazing Location Lakefront Waterside Deck

1149 Old Queen Anne Rd, Chatham, United States Show map

The 4-bedroom Amazing Location Lakefront Waterside Deck Chatham villa offers proximity to such city sites as Goose Pond, located only a 5-minute walk away. The Chatham holiday home features… More

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Perfect For Group W Kids & Dogs W Hot Tub

29 Cleo Ln, Chatham, United States Show map

The 4-bedroom Perfect For Group W Kids & Dogs W Hot Tub Villa Chatham, located nearly 10 minutes' walk from the Forest Beach, invites guests to relax in a Jacuzzi. More

From US$ 906 Book Now

Steps To Oyster Pond Private Dock!

47 Capri Ln, Chatham, United States Show map

Steps To Oyster Pond Private Dock! Villa Chatham is situated only 5 minutes on foot from the Oyster Pond, featuring such comforts as high-speed Internet access and private car parking. Offering… More

From US$ 876 Book Now