A windmill, a boat, and a beach.

Find hotels near Chatham Windmill, Chatham from $69

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Sep 1 - Sep 2
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Sep 2 - Sep 3
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Sep 4 - Sep 6
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Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

Old Harbor Inn
0.5 mi from Chatham Windmill
United States
Pamela
$441 nightly
$505 total
Sep 20 - Sep 21
Total with taxes and fees
Old Harbor Inn

2. Chatham Wayside Inn

Chatham Wayside Inn
0.3 mi from Chatham Windmill
United States
jacquelyn
$337 nightly
$386 total
Sep 29 - Sep 30
Total with taxes and fees
Chatham Wayside Inn

3. Greyfinch Chatham Inn

Greyfinch Chatham Inn
0.9 mi from Chatham Windmill
United Kingdom
Sara
$210 nightly
$240 total
Oct 1 - Oct 2
Total with taxes and fees
Greyfinch Chatham Inn

4. Surfside Inn Chatham

Surfside Inn Chatham
0.5 mi from Chatham Windmill
United States
Jenee
$235 nightly
$269 total
Oct 1 - Oct 2
Total with taxes and fees
Surfside Inn Chatham

5. Pleasant Bay Village Resort

Pleasant Bay Village Resort
2.8 mi from Chatham Windmill
United States
Allison
$239 nightly
$274 total
Sep 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort

6. Olde Tavern Motel And Inn

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

7. Charm on Main by Ocean Edge

Charm on Main by Ocean Edge
8.2 mi from Chatham Windmill
United States
Kathleen
$171 nightly
$195 total
Sep 3 - Sep 4
Total with taxes and fees
Charm on Main by Ocean Edge

8. Skaket Beach Motel

Skaket Beach Motel
7.5 mi from Chatham Windmill
United States
Jason
$137 nightly
$157 total
Sep 15 - Sep 16
Total with taxes and fees
Skaket Beach Motel

9. Dennis Port Surf Club (Boutique Hotel)

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

10. Sea Meadow Inn

Sea Meadow Inn
9.2 mi from Chatham Windmill
United States
Joanne
$254 nightly
$290 total
Oct 1 - Oct 2
Total with taxes and fees
Sea Meadow Inn

11. Chatham Seafarer Inn

Chatham Seafarer Inn
2.6 mi from Chatham Windmill
United States
Nicholas
$194 nightly
$222 total
Sep 22 - Sep 23
Total with taxes and fees
Chatham Seafarer Inn

12. Kingfisher Harwich Port

Kingfisher Harwich Port
6 mi from Chatham Windmill
United States
Marc
$230 nightly
$263 total
Sep 7 - Sep 8
Total with taxes and fees
Kingfisher Harwich Port

13. Chatham Tides

Chatham Tides
3.9 mi from Chatham Windmill
United States
Melissa
$311 nightly
$356 total
Oct 1 - Oct 2
Total with taxes and fees
Chatham Tides

14. Brewster Green Resort

Brewster Green Resort
7.5 mi from Chatham Windmill
United States
Jim
$177 nightly
$203 total
Sep 24 - Sep 25
Total with taxes and fees
Brewster Green Resort

15. The Tern Inn Bed & Breakfast and Cottages

The Tern Inn Bed & Breakfast and Cottages
7.7 mi from Chatham Windmill
United States
Donald
$210 nightly
$240 total
Sep 10 - Sep 11
Total with taxes and fees
The Tern Inn Bed & Breakfast and Cottages

16. Blue Rock Resort

Blue Rock Resort
11.4 mi from Chatham Windmill
United States
Patricia
$111 nightly
$127 total
Sep 2 - Sep 3
Total with taxes and fees
Blue Rock Resort

17. GuestLodge

GuestLodge
11.1 mi from Chatham Windmill
United States
John
$60 nightly
$69 total
Sep 21 - Sep 22
Total with taxes and fees
GuestLodge

18. Kingfisher Oceanside

Kingfisher Oceanside
9.2 mi from Chatham Windmill
United States
David
$179 nightly
$205 total
Sep 7 - Sep 8
Total with taxes and fees
Kingfisher Oceanside

19. Lighthouse Inn

Lighthouse Inn
11 mi from Chatham Windmill
United States
Craig
$149 nightly
$171 total
Sep 16 - Sep 17
Total with taxes and fees
Lighthouse Inn

20. Handkerchief Shoals Inn

Handkerchief Shoals Inn
4.6 mi from Chatham Windmill
United States
David
$134 nightly
$153 total
Sep 17 - Sep 18
Total with taxes and fees
Handkerchief Shoals Inn
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Compare popular hotels close to Chatham Windmill

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Hiking
Old Harbor Inn
9.6
Exceptional
168 reviews
View
Beach
Chatham Wayside Inn
9.2
Wonderful
725 reviews
View
Outdoor pool
Greyfinch Chatham Inn
8.8
Excellent
280 reviews
View
Porch
Surfside Inn Chatham
8.2
Very Good
170 reviews
View
Pool waterfall
Pleasant Bay Village Resort
9.6
Exceptional
328 reviews
View

Top Chatham Windmill Hotel Reviews

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Nice location and cute hotel! The staff was great, and the restaurant was really good!"
Nicole Ann 1-night trip
Posted 1 hour ago
Chatham Wayside Inn
Queen Anne Inn

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."
Julia 2-night trip
Posted 1 day ago
Queen Anne Inn
Cozy Cape near Chatham Center

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!"
Abigail T. 3-night trip
Posted 3 days ago
Cozy Cape near Chatham Center
Private Beach, Water Views, Incredible Location!

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."
Therese Q. 6-night trip
Posted 3 days ago
Private Beach, Water Views, Incredible Location!
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

10/10 Excellent
"Lovely location, well equipped home, great selection of toys for kids"
Denise G. 7-night trip
Posted 3 days ago
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Old Harbor Inn

Old Harbor Inn

10/10 Excellent
"The owner was so nice and knowledgeable. He made us feel like home."
Pamela 3-night trip
Posted 6 days ago
Old Harbor Inn
Chatham Village:  Lovely 1-Bedroom Apartment in Antique 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."
Emily B. 2-night trip
Posted 10 days ago
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 12 days ago
Greyfinch Chatham Inn
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

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!"
Shawna H. 3-night trip
Posted 13 days ago
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

Other attractions near Chatham Windmill

A lighthouse with a glass enclosure and metal railing, set against a partly cloudy sky.

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.
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A baseball game at night with players on the field and a house in the background.

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.
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A beach with people walking and standing on the sand, and the ocean in the background.

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.
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Chase Park

You can take time to visit Chase Park during your travels to Chatham. Wander the beautiful beaches in this trendy area.
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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.
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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.
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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.
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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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Frequently asked questions

What are the top-rated hotels near Chatham Windmill?
Discover some of the top-rated hotels near Chatham Windmill, perfect for an unforgettable stay in Chatham, Massachusetts.Captain's House InnCaptain's House Inn is a charming 4-star hotel located just 1.3 miles from Chatham Windmill, with an impressive review rating of 9.8. Guests can indulge in the serene atmosphere with amenities such as a private beach nearby, complimentary full breakfast, and cozy fireplaces in the rooms. The beautifully designed patio and terrace offer perfect spots to relax, while kayaking and boat tours are available at a nearby location, enhancing the coastal experience.Old Harbor InnOld Harbor Inn, rated 9.6 by travelers, is a delightful 3.5-star hotel situated just a short 12-minute walk from Chatham Windmill. This inn features a lovely terrace and offers a buffet breakfast, alongside unique amenities like on-site yoga classes and romantic champagne service. Guests appreciate the beach umbrellas for a day by the shore and the cozy fireplaces in the rooms, making it a great choice for a relaxing getaway.Pleasant Bay Village ResortPleasant Bay Village Resort is a welcoming 3-star hotel located 3.2 miles from Chatham Windmill, with an excellent review rating of 9.6. The resort features an inviting outdoor pool and a hot tub for ultimate relaxation. Guests can enjoy the convenience of kitchenettes in their rooms and access to self-parking. With a lovely garden and playground, this resort provides a serene environment perfect for unwinding after a day of exploring.
What hotels are within walking distance to Chatham Windmill?
Discover some top-rated hotels within walking distance to Chatham Windmill that promise a delightful stay in Chatham, Massachusetts.Old Harbor InnOld Harbor Inn offers an inviting atmosphere just a 12-minute walk from Chatham Windmill. Rated 9.6 by travelers, this 3.5-star hotel features a lovely terrace, complimentary daily breakfast, and convenient early check-in. Guests can unwind with yoga classes onsite or enjoy a romantic picnic in the garden. With amenities like beach towels and self-parking, this is an ideal spot for relaxation and exploration.The HawthorneThe Hawthorne is a charming escape located only 17 minutes on foot from Chatham Windmill, a review rating of 9.4. This hotel features a kitchenette in every room, perfect for longer stays. Guests can soak up the sun at the nearby private beach or enjoy ocean views from the terrace. With self-parking and beach sun loungers available, it's a comfortable choice for those looking to enjoy the coastal experience.Chatham Bars InnChatham Bars Inn, a luxurious 5-star hotel, is just an 18-minute stroll from Chatham Windmill and holds a review rating of 9.2. Guests can indulge in a full-service spa, outdoor tennis, and a beach shuttle. The hotel offers stunning ocean views and features a health club, swimming pool, and on-site dining. With amenities like valet parking and exclusive beach cabanas, this inn ensures a premium coastal retreat.
How much is a hotel near Chatham Windmill?
Staying near Chatham Windmill is a treat, with plenty of hotels from $69 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Chatham Windmill?
For families looking for top-rated hotels near Chatham Windmill, there are several excellent options that cater to both comfort and fun for all ages.Chatham Wayside InnChatham Wayside Inn, located just a 7-minute walk from Chatham Windmill, is a charming 4-star hotel with a strong travelers' rating of 9.2. Families can enjoy amenities like a kid-friendly restaurant, games for children, and free cribs. The inn also features a relaxing pool, garden views, and complimentary breakfast, making it an inviting option for families looking to explore the area.Greyfinch Chatham InnGreyfinch Chatham Inn is a delightful 3-star hotel located just 1.1 miles from Chatham Windmill, a travelers' rating of 8.8. This family-friendly inn offers amenities such as free cribs, a kitchenette, and rollaway beds to accommodate families. Guests can enjoy the pool with sun loungers, a lovely garden area, and easy access to nearby sandy beaches, making it a perfect retreat for families.Wequassett Resort and Golf ClubWequassett Resort and Golf Club is a luxurious 5-star resort situated 4.5 miles from Chatham Windmill and is highly rated by travelers with a score of 9.4. Families will appreciate the children's club, playground, and connecting rooms, ensuring a comfortable stay. The hotel also features a stunning pool, on-site dining with kids' meals, and a range of outdoor activities including golf and tennis, perfect for family adventures.
Are there any 5-star hotels near Chatham Windmill?
Discover top-rated hotels near Chatham Windmill that combine luxury and breathtaking surroundings for an unforgettable stay.Chatham Bars InnChatham Bars Inn is an exquisite 5-star hotel situated just an 18-minute walk from Chatham Windmill, rated 9.2 by travelers. This waterfront hotel boasts stunning ocean views and a variety of luxurious amenities. Guests can indulge in the full-service spa, relax at the outdoor pool, or enjoy beach access with complimentary beach shuttles. The inn also features tennis courts and gourmet dining with ocean views, making it a remarkable choice for an elegant getaway.Wequassett Resort and Golf ClubWequassett Resort and Golf Club is a stunning 5-star retreat located just 4.5 miles from Chatham Windmill. With an impressive review rating of 9.4, this resort offers a perfect blend of relaxation and adventure. Guests can enjoy direct access to a private beach, a luxurious pool area with cabanas, and golf nearby. Unique amenities include an extensive wellness program featuring yoga classes and an onsite sailing experience, ensuring a memorable stay for all travelers.
Which hotels near Chatham Windmill offer the best views?
Discover the top-rated hotels near Chatham Windmill that offer stunning views and memorable experiences.Chatham Wayside InnChatham Wayside Inn is a charming 4-star hotel, just a 7-minute walk from Chatham Windmill, rated 9.2 by travelers. With a lovely terrace and garden view restaurant, it offers a cozy atmosphere for travelers. The inn features a heated pool, complimentary breakfast, and is conveniently located near local shopping. Ideal for those seeking a relaxing getaway with easy access to scenic spots.Chatham Bars InnChatham Bars Inn offers an enchanting stay just an 18-minute walk from Chatham Windmill, a review rating of 9.2. This elegant 5-star hotel features stunning ocean views and direct beach access, along with a full-service spa, tennis courts, and complimentary beach shuttle service. Guests can unwind at the beachfront bar or indulge in relaxing treatments at the spa, ensuring a rejuvenating experience in a picturesque setting.Wequassett Resort and Golf ClubWequassett Resort and Golf Club, rated 9.4 by travelers, is a luxurious 5-star retreat located 4.5 miles from Chatham Windmill. Guests can enjoy breathtaking ocean views from the on-site restaurant, alongside exceptional amenities like a hot tub, a full-service spa, and direct beach access. The hotel also features a golf course nearby, making it perfect for golf enthusiasts who appreciate a scenic landscape.
What are the best affordable hotels near Chatham Windmill?
For those seeking affordable accommodations near Chatham Windmill, these top-rated options strike a perfect balance between comfort and value, providing great amenities for families and travelers alike.Pleasant Bay Village ResortPleasant Bay Village Resort, a charming 3-star hotel located just 3.2 miles from Chatham Windmill, offers travelers a warm, family-friendly atmosphere. With an impressive review rating of 9.6, travelers can enjoy amenities such as a hot tub, outdoor pool, and daily housekeeping. Families will appreciate the playground and cribs available on request, along with convenient features like free WiFi and self-parking.The HawthorneThe Hawthorne is a delightful choice for travelers, located within a 17-minute walk from Chatham Windmill and a great traveler rating score of 9.4. This hotel features ocean views and access to a sandy beach, making it ideal for those who enjoy coastal relaxation. Guests will find amenities such as free WiFi, self-parking, and kitchenettes for added convenience, along with beach towels and loungers for a perfect day by the water.The Chatham MotelThe Chatham Motel, situated just 2.1 miles from Chatham Windmill, is a fantastic option for budget-conscious travelers, rated 9.2 by travelers. This welcoming motel offers essential amenities like free WiFi and self-parking, along with a refreshing outdoor pool and playground for children. Guests will also enjoy the convenience of kitchenettes and microwaves in their rooms, making it easy to prepare meals during their stay.
What are the best boutique hotels near Chatham Windmill?
For travelers seeking a boutique experience near Chatham Windmill, there are some top-rated hotels that offer unique charm and exceptional amenities.Chatham Bars InnChatham Bars Inn is a luxurious 5-star hotel situated within an 18-minute walk from Chatham Windmill, offering an impressive travelers' rating of 9.2. This boutique hotel is perfect for families, featuring supervised childcare, a children's club, and a relaxing beachfront with beach cabanas. Guests can also indulge in spa services, tranquil ocean views, and convenient amenities such as a beach shuttle and tennis courts for a complete seaside retreat.Wequassett Resort and Golf ClubWequassett Resort and Golf Club, a 5-star gem located just 4.5 miles from Chatham Windmill, features a stunning array of boutique amenities and a remarkable travelers' rating of 9.4. This family-friendly resort boasts a children's club, babysitting services, and a poolside bar, ensuring a delightful stay for travelers of all ages. Additional amenities include an onsite golf course, hot tub, and a variety of water sports such as kayaking and windsurfing.
Are there any hotels with pools close to Chatham Windmill?
For travelers seeking a refreshing getaway near Chatham Windmill, here are some top-rated hotels with pools that promise a delightful stay.Chatham Wayside InnChatham Wayside Inn is a charming 4-star hotel located just a 7-minute walk from Chatham Windmill, featuring an inviting outdoor pool complete with sun loungers and accessible options for all travelers. Rated 9.2 by travelers, this family-friendly hotel offers complimentary breakfast, a lovely garden view restaurant, and nearby golf and beach activities to ensure a memorable stay.Chatham Bars InnJust an 18-minute walk from Chatham Windmill, Chatham Bars Inn is a prestigious 5-star hotel a top review rating of 9.2. Guests can enjoy a beautifully designed pool area, complete with accessibility features and spa treatments. This upscale hotel also offers complimentary beach shuttles, tennis courts, and a full-service spa, ensuring a luxurious and relaxing experience for families and couples alike.Wequassett Resort and Golf ClubWequassett Resort and Golf Club, a luxurious 5-star retreat, is situated 4.5 miles from Chatham Windmill. With a fantastic review rating of 9.4, travelers can indulge in a stunning pool area featuring cabanas and a poolside bar. This resort also offers activities like sailing and windsurfing, alongside exquisite dining options and family amenities like a children's club, making it perfect for a lavish family escape.
What are the best pet-friendly hotels near Chatham Windmill?
Finding the perfect pet-friendly stay near Chatham Windmill is a breeze with these top-rated hotels that welcome your furry friends.Wequassett Resort and Golf ClubWequassett Resort and Golf Club is a luxurious 5-star hotel located just 4.5 miles from Chatham Windmill, with an impressive review rating of 9.4. This resort is ideal for travelers traveling with pets, offering amenities such as pet-friendly rooms and food and water bowls. Guests can enjoy a range of features including an onsite golf course, outdoor pool, and a relaxing beach area. With options for fine dining and activities like tennis and kayaking, this resort promises a delightful stay for both you and your pet.
Can I book a fully refundable hotel close to Chatham Windmill?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Chatham Windmill", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

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