Chatham Windmill

Photo by George Sykes
Photo by George Sykes

Plan a trip to see Chatham Windmill

Price found within the past 48 hours. Click for updated prices.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥257,578, price is now ￥201,923 per person
￥201,923
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
Everything about this place is right! One of the nicest hotels we've ever stayed at.

Reviewed on Sep 5, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥306,860, price is now ￥214,933 per person
￥214,933
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on Sep 15, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥288,364, price is now ￥226,598 per person
￥226,598
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This is one of the nicest hotels I’ve stayed in—it’s a beautiful, well-located property with top-notch front desk staff and many thoughtful extras.

Reviewed on Sep 18, 2025

Popular places to visit

Chatham Lighthouse

Chatham Lighthouse

Learn about the local history of Chatham when you spend time at Chatham Lighthouse. Wander the beautiful beaches and seaside in this trendy area.

Chatham Lighthouse
Enjoy the view, watch the fishing boats come in and unload their catch, and pick up fresh fish or seafood to take home for dinner at the market.

Chatham Fish Pier

Explore the waterfront in Chatham with a trip to Chatham Fish Pier. Wander the beautiful beaches and seaside in the area.

Chatham Fish Pier

Mayo House

Learn about the local history of Chatham when you take a trip to Mayo House. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Mayo House

Gallery Antonia

You can spend an afternoon studying the exhibits at Gallery Antonia during your travels in Chatham. Stroll along the area's seaside, or simply savor its seafood restaurants.

Gallery Antonia

Atwood House Museum

You can spend an afternoon studying the exhibits at Atwood House Museum during your travels in Chatham. Stroll along the beautiful beaches in this trendy area, or check out its seafood restaurants.

Atwood House Museum

Monomoy Theatre

You can get tickets for a performance at Monomoy Theatre during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Monomoy Theatre

Best Lodging Options Near Chatham Windmill

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
Chatham Wayside Inn
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St, Chatham, MA
Surfside Inn Chatham
The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd, Chatham, MA
The Hawthorne
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach

Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach

Chatham
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

4 out of 5
Chatham
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Old Harbor Inn

Old Harbor Inn

3.5 out of 5
22 Old Harbor Rd., Chatham, MA
Old Harbor Inn
See all 3,017 properties in Chatham Windmill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.