A windmill, a boat, and a beach.

Find hotels near Chatham Windmill, Chatham from $107

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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
Maria
$441 nightly
$505 total
Sep 20 - Sep 21
Total with taxes and fees
Old Harbor Inn

2. Chatham Bars Inn

Chatham Bars Inn
0.7 mi from Chatham Windmill
United States
Yousuf Hussain
$561 nightly
$642 total
Sep 20 - Sep 21
Total with taxes and fees
Chatham Bars Inn

3. Chatham Wayside Inn

Chatham Wayside Inn
0.3 mi from Chatham Windmill
United States
Nicole Ann
$397 nightly
$454 total
Sep 29 - Sep 30
Total with taxes and fees
Chatham Wayside Inn

4. 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

5. 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

6. 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

7. Candleberry Inn on Cape Cod

Candleberry Inn on Cape Cod
8.7 mi from Chatham Windmill
United States
Christopher
$314 nightly
$359 total
Sep 7 - Sep 8
Total with taxes and fees
Candleberry Inn on Cape Cod

8. Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod
9.2 mi from Chatham Windmill
United States
Timothy
$169 nightly
$193 total
Oct 7 - Oct 8
Total with taxes and fees
Eagle Wing Inn - Cape Cod

9. Charm on Main by Ocean Edge

Charm on Main by Ocean Edge
8.2 mi from Chatham Windmill
United States
Kathleen
$185 nightly
$212 total
Sep 7 - Sep 8
Total with taxes and fees
Charm on Main by Ocean Edge

10. The Captain Farris House B&B

The Captain Farris House B&B
11.8 mi from Chatham Windmill
United States
Timothy
$167 nightly
$190 total
Oct 4 - Oct 5
Total with taxes and fees
The Captain Farris House B&B

11. Ship's Knees Inn

Ship's Knees Inn
7.8 mi from Chatham Windmill
United States
Elizabeth
$307 nightly
$351 total
Oct 4 - Oct 5
Total with taxes and fees
Ship's Knees Inn

12. Chatham Tides

Chatham Tides
3.9 mi from Chatham Windmill
United States
Melissa
$236 nightly
$270 total
Oct 7 - Oct 8
Total with taxes and fees
Chatham Tides

13. Doryman Motel

Doryman Motel
9.1 mi from Chatham Windmill
United States
Leslie
$170 nightly
$195 total
Sep 20 - Sep 21
Total with taxes and fees
Doryman Motel

14. Dennis Port Surf Club (Boutique Hotel)

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

15. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
3.7 mi from Chatham Windmill
United States
Lisa
$626 nightly
$716 total
Sep 7 - Sep 8
Total with taxes and fees
Wequassett Resort and Golf Club

16. The Escape Inn

The Escape Inn
12.1 mi from Chatham Windmill
United States
Chad
$94 nightly
$107 total
Oct 1 - Oct 2
Total with taxes and fees
The Escape Inn

17. Skaket Beach Motel

Skaket Beach Motel
7.5 mi from Chatham Windmill
United States
Jason
$129 nightly
$147 total
Oct 7 - Oct 8
Total with taxes and fees
Skaket Beach Motel

18. The Villa Callo Inn

The Villa Callo Inn
8.5 mi from Chatham Windmill
United States
Shawn
$383 nightly
$439 total
Sep 14 - Sep 15
Total with taxes and fees
The Villa Callo Inn

19. Sesuit Harbor House

Sesuit Harbor House
11.7 mi from Chatham Windmill
Canada
Natasha
$291 nightly
$333 total
Oct 1 - Oct 2
Total with taxes and fees
Sesuit Harbor House

20. Kingfisher Oceanside

Kingfisher Oceanside
9.2 mi from Chatham Windmill
United States
David
$162 nightly
$186 total
Sep 8 - Sep 9
Total with taxes and fees
Kingfisher Oceanside
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Compare popular hotels close to Chatham Windmill

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A sandy beach path with wooden fencing, leading to the ocean.
Old Harbor Inn
9.6
Exceptional
169 reviews
View
A pathway leading to a beach with boats in the background and a building with a tower.
Chatham Bars Inn
9.2
Wonderful
859 reviews
View
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
Chatham Wayside Inn
9.2
Wonderful
726 reviews
View
Four sun loungers aligned along a poolside with a tiled floor.
Greyfinch Chatham Inn
8.8
Excellent
280 reviews
View
A covered porch with wicker furniture and a red cushion, a brick pathway, and a grassy area with a sign in the background.
Surfside Inn Chatham
8.2
Very Good
171 reviews
View

Top Chatham Windmill Hotel Reviews

Old Harbor Inn

Old Harbor Inn

10/10 Excellent
"Absolutely loved our stay at the inn! The whole inn is so charming and the staff (including the owners Ray and Judy) were the best!!! They serve breakfast every morning, which was so good and they also had baked goods available all day and it was also phenomenal. We were very impressed how well the property was maintained and it’s nice that the inn is slightly off of Main Street which made it quieter experience. I highly recommend this inn!"
Maria 4-night trip
Posted 20 hours ago
Old Harbor Inn
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

10/10 Excellent
"Could not have asked for a better Chatham experience. The house is beautiful, spacious and incredibly comfortable, with plenty of room for everyone to gather while still having space to spread out.The location is truly exceptional. Being right on the water made mornings and evenings at the house feel special, and we loved being able to walk into town and to the beach so easily. The backyard and patio were particular favorites—perfect for coffee in the morning, cocktails at the end of the day and simply taking in the view.The house was spotless, thoughtfully equipped and had everything we needed for a relaxed stay with friends. It’s one of those rare rentals that feels even better in person than it looks in the photos.We made some very happy memories here and would absolutely stay again."
Melissa W. 6-night trip
Posted 21 hours ago
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Water View-Walk town/beach, pets considered, Linen Option

Water View-Walk town/beach, pets considered, Linen Option

10/10 Excellent
"A wonderful house in a great location. We will be back!"
jacqueline h. 7-night trip
Posted 21 hours ago
Water View-Walk town/beach, pets considered, Linen Option
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Clean room, nice staff, no laundry on site, property could use upgrades."
Claudia 2-night trip
Posted 2 days ago
Chatham Wayside 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 8 days ago
Cozy Cape near Chatham Center
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 2 weeks 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 2 weeks 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 3 weeks ago
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

10/10 Excellent
"Our family loves this charming cottage and its close proximity to town! Charming in style and comfortable to relax with a book! Thanks for sharing your piece of Cape Cod!"
Kathi S. 7-night trip
Posted 2 months ago
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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 seaside, 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 $107 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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