
Find hotels near Chatham Windmill, Chatham from $69
Check prices for these dates
Tonight
Sep 1 - Sep 2Tomorrow
Sep 2 - Sep 3This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13 Our top choices for Chatham Windmill hotels




1. Old Harbor Inn
Old Harbor Inn0.5 mi from Chatham Windmill
Pamela
$441 nightly
$505 total
Sep 20 - Sep 21
Total with taxes and fees




2. Chatham Wayside Inn
Chatham Wayside Inn0.3 mi from Chatham Windmill
jacquelyn
$337 nightly
$386 total
Sep 29 - Sep 30
Total with taxes and fees




3. Greyfinch Chatham Inn
Greyfinch Chatham Inn0.9 mi from Chatham Windmill
Sara
$210 nightly
$240 total
Oct 1 - Oct 2
Total with taxes and fees




4. Surfside Inn Chatham
Surfside Inn Chatham0.5 mi from Chatham Windmill
Jenee
$235 nightly
$269 total
Oct 1 - Oct 2
Total with taxes and fees




5. Pleasant Bay Village Resort
Pleasant Bay Village Resort2.8 mi from Chatham Windmill
Allison
$239 nightly
$274 total
Sep 22 - Sep 23
Total with taxes and fees




6. Olde Tavern Motel And Inn
Olde Tavern Motel And Inn7.6 mi from Chatham Windmill
Rosalie
$112 nightly
$128 total
Sep 2 - Sep 3
Total with taxes and fees




7. Charm on Main by Ocean Edge
Charm on Main by Ocean Edge8.2 mi from Chatham Windmill
Kathleen
$171 nightly
$195 total
Sep 3 - Sep 4
Total with taxes and fees




8. Skaket Beach Motel
Skaket Beach Motel7.5 mi from Chatham Windmill
Jason
$137 nightly
$157 total
Sep 15 - Sep 16
Total with taxes and fees




9. Dennis Port Surf Club (Boutique Hotel)
Dennis Port Surf Club (Boutique Hotel)9.2 mi from Chatham Windmill
Jose Alejandro
$98 nightly
$112 total
Sep 9 - Sep 10
Total with taxes and fees




10. Sea Meadow Inn
Sea Meadow Inn9.2 mi from Chatham Windmill
Joanne
$254 nightly
$290 total
Oct 1 - Oct 2
Total with taxes and fees




11. Chatham Seafarer Inn
Chatham Seafarer Inn2.6 mi from Chatham Windmill
Nicholas
$194 nightly
$222 total
Sep 22 - Sep 23
Total with taxes and fees




12. Kingfisher Harwich Port
Kingfisher Harwich Port6 mi from Chatham Windmill
Marc
$230 nightly
$263 total
Sep 7 - Sep 8
Total with taxes and fees




13. Chatham Tides
Chatham Tides3.9 mi from Chatham Windmill
Melissa
$311 nightly
$356 total
Oct 1 - Oct 2
Total with taxes and fees




14. Brewster Green Resort
Brewster Green Resort7.5 mi from Chatham Windmill
Jim
$177 nightly
$203 total
Sep 24 - Sep 25
Total with taxes and fees




15. The Tern Inn Bed & Breakfast and Cottages
The Tern Inn Bed & Breakfast and Cottages7.7 mi from Chatham Windmill
Donald
$210 nightly
$240 total
Sep 10 - Sep 11
Total with taxes and fees




16. Blue Rock Resort
Blue Rock Resort11.4 mi from Chatham Windmill
Patricia
$111 nightly
$127 total
Sep 2 - Sep 3
Total with taxes and fees




17. GuestLodge
GuestLodge11.1 mi from Chatham Windmill
John
$60 nightly
$69 total
Sep 21 - Sep 22
Total with taxes and fees




18. Kingfisher Oceanside
Kingfisher Oceanside9.2 mi from Chatham Windmill
David
$179 nightly
$205 total
Sep 7 - Sep 8
Total with taxes and fees




19. Lighthouse Inn
Lighthouse Inn11 mi from Chatham Windmill
Craig
$149 nightly
$171 total
Sep 16 - Sep 17
Total with taxes and fees




20. Handkerchief Shoals Inn
Handkerchief Shoals Inn4.6 mi from Chatham Windmill
David
$134 nightly
$153 total
Sep 17 - Sep 18
Total with taxes and fees
Compare popular hotels close to Chatham Windmill
Property | Star rating | Guest rating | Breakfast included | Pool | Spa | Pet friendly | WiFi included |
|---|---|---|---|---|---|---|---|
![]() Old Harbor Inn | 9.6 Exceptional 168 reviews | View | |||||
![]() Chatham Wayside Inn | 9.2 Wonderful 725 reviews | View | |||||
![]() Greyfinch Chatham Inn | 8.8 Excellent 280 reviews | View | |||||
![]() Surfside Inn Chatham | 8.2 Very Good 170 reviews | View | |||||
![]() Pleasant Bay Village Resort | 9.6 Exceptional 328 reviews | View |
Top Chatham Windmill Hotel Reviews
Chatham Wayside Inn
10/10 Excellent
"Nice location and cute hotel! The staff was great, and the restaurant was really good!"
Queen Anne Inn
8/10 Good
"7/10 — Charming property with room for improvement We stayed for two nights this past weekend and overall had a pleasant stay. We were in the back cottage, and the room itself was totally fine. I especially liked the hardwood floors, and we had no major concerns with the room during our stay. The bathroom could use some updating, but everything was functional. The main building has a cute, eclectic New England feel, with some really charming sitting areas and common spaces. There’s definitely a lot of character to the property, and with a few updates and a little more attention to the grounds, I think it could be a really lovely place. One area that stood out was the upkeep of the outdoor spaces. There were tables and chairs with quite a few fallen leaves sitting on them throughout the weekend, which made the outdoor areas feel a bit less inviting than they could have been. A little more regular maintenance would make a noticeable difference. The front desk receptionist was wonderful. She was very friendly and checked in with us a couple of times throughout the weekend to make sure everything was going well and that we didn’t need anything, which we really appreciated. Overall, we had a good stay and everything went smoothly. The property has a lot of charm and potential, and I think some updates to the bathrooms and a bit more attention to the outdoor grounds could really elevate the experience."
Cozy Cape near Chatham Center
10/10 Excellent
"The house was perfect and in a great location, and the host was very kind and responsive! Would definitely stay again!"
Private Beach, Water Views, Incredible Location!
10/10 Excellent
"We stayed here for 6 nights with 2 of our adult children. The house was beautiful in an exceptionally quiet, peaceful setting with panoramic views and a wrap around deck. The house was comfortable and pristine with a beautiful kitchen that was very well stocked with everything you’d need for cooking in and very nice bathrooms with great showers! Chatham is centrally located for quick trips to many public beaches. We visited Chatham beaches, Nauset beach and Corporation Beach. We were able to watch seals from the private beach one night."
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
10/10 Excellent
"Lovely location, well equipped home, great selection of toys for kids"
Old Harbor Inn
10/10 Excellent
"The owner was so nice and knowledgeable. He made us feel like home."
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
10/10 Excellent
"First time to the Cape- Loved the location and ease of getting a copy of coffee with a short walk to town. Everything was clean and quiet. Thank you for such a great place to stay."
Greyfinch Chatham Inn
10/10 Excellent
"Clean room and great location"
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
10/10 Excellent
"Beautiful property is great location! Very comfortable, quiet and centrally located. Susan was an excellent host!"
Other attractions near Chatham Windmill

Chatham Lighthouse
9.4/10 (173 reviews)
One of the most photographed of Cape Cod’s historic lighthouses overlooks a beautiful, white sand beach that’s great for fun in the sun.

Veterans Field
9.6/10 (9 reviews)
Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Chatham Lighthouse Beach
9.2/10 (46 reviews)
Offering a fun seaside escape for the whole family, this beautiful beach is one of the largest in Chatham and features an iconic lighthouse.
Chase Park
You can take time to visit Chase Park during your travels to Chatham. Wander the beautiful beaches in this trendy area.
Mayo House
8.0/10 (3 reviews)
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.
Atwood House Museum
6.0/10 (1 review)
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.
Chatham Seaside Links
9.2/10 (20 reviews)
Enjoy a round of golf in Chatham at Chatham Seaside Links. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
Chatham Railroad Museum
8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chatham Railroad Museum during your travels in Chatham. Stroll along the area's beautiful beaches, or simply savor its seafood restaurants.
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