A windmill, a boat, and a beach.

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Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

Old Harbor Inn
0.8 km from Chatham Windmill
United States
Pamela
CA $611
CA $699 total
includes taxes & fees
Sep 20 - Sep 21
Old Harbor Inn

2. Chatham Wayside Inn

Chatham Wayside Inn
0.5 km from Chatham Windmill
United States
jacquelyn
CA $499
CA $632 total
includes taxes & fees
Sep 29 - Sep 30
Chatham Wayside Inn

3. Greyfinch Chatham Inn

Greyfinch Chatham Inn
1.5 km from Chatham Windmill
United Kingdom
Sara
CA $261
CA $349 total
includes taxes & fees
Oct 1 - Oct 2
Greyfinch Chatham Inn

4. Surfside Inn Chatham

Surfside Inn Chatham
0.8 km from Chatham Windmill
United States
Jenee
CA $326
CA $373 total
includes taxes & fees
Oct 1 - Oct 2
Surfside Inn Chatham

5. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
12.3 km from Chatham Windmill
Canada
Rosalie
CA $128
CA $147 total
includes taxes & fees
Sep 2 - Sep 3
Olde Tavern Motel And Inn

6. Pleasant Bay Village Resort

Pleasant Bay Village Resort
4.5 km from Chatham Windmill
United States
Allison
CA $320
CA $366 total
includes taxes & fees
Sep 28 - Sep 29
Pleasant Bay Village Resort

7. Charm on Main by Ocean Edge

Charm on Main by Ocean Edge
13.2 km from Chatham Windmill
United States
Kathleen
CA $246
CA $282 total
includes taxes & fees
Sep 2 - Sep 3
Charm on Main by Ocean Edge

8. Skaket Beach Motel

Skaket Beach Motel
12 km from Chatham Windmill
United States
Jason
CA $190
CA $218 total
includes taxes & fees
Sep 28 - Sep 29
Skaket Beach Motel

9. GuestLodge

GuestLodge
17.9 km from Chatham Windmill
United States
John
CA $83
CA $95 total
includes taxes & fees
Sep 21 - Sep 22
GuestLodge

10. Kingfisher Harwich Port

Kingfisher Harwich Port
9.6 km from Chatham Windmill
United States
Marc
CA $318
CA $364 total
includes taxes & fees
Sep 7 - Sep 8
Kingfisher Harwich Port

11. Chatham Seafarer Inn

Chatham Seafarer Inn
4.2 km from Chatham Windmill
United States
Nicholas
CA $293
CA $335 total
includes taxes & fees
Sep 17 - Sep 18
Chatham Seafarer Inn

12. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
14.8 km from Chatham Windmill
United States
Jose Alejandro
CA $138
CA $157 total
includes taxes & fees
Sep 2 - Sep 3
Dennis Port Surf Club (Boutique Hotel)

13. Blue Rock Resort

Blue Rock Resort
18.3 km from Chatham Windmill
United States
Patricia
CA $149
CA $172 total
includes taxes & fees
Sep 8 - Sep 9
Blue Rock Resort

14. Handkerchief Shoals Inn

Handkerchief Shoals Inn
7.3 km from Chatham Windmill
United States
David
CA $185
CA $212 total
includes taxes & fees
Sep 17 - Sep 18
Handkerchief Shoals Inn

15. Lighthouse Inn

Lighthouse Inn
17.7 km from Chatham Windmill
United States
Craig
CA $188
CA $215 total
includes taxes & fees
Sep 10 - Sep 11
Lighthouse Inn

16. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
13.2 km from Chatham Windmill
United States
Kurt
CA $147
CA $168 total
includes taxes & fees
Oct 1 - Oct 2
Rodeway Inn Orleans - Cape Cod

17. Sea Meadow Inn

Sea Meadow Inn
14.9 km from Chatham Windmill
United States
Joanne
CA $403
CA $468 total
includes taxes & fees
Oct 1 - Oct 2
Sea Meadow Inn

18. The Tern Inn Bed & Breakfast and Cottages

The Tern Inn Bed & Breakfast and Cottages
12.5 km from Chatham Windmill
United States
Donald
CA $245
CA $280 total
includes taxes & fees
Sep 22 - Sep 23
The Tern Inn Bed & Breakfast and Cottages

19. Brewster Green Resort

Brewster Green Resort
12 km from Chatham Windmill
United States
Jim
CA $252
CA $288 total
includes taxes & fees
Sep 24 - Sep 25
Brewster Green Resort

20. The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort
13.8 km from Chatham Windmill
United States
Pamela
CA $187
CA $226 total
includes taxes & fees
Sep 14 - Sep 15
The Corsair & Cross Rip Oceanfront Resort
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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
168 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
723 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
170 reviews
View
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
Olde Tavern Motel And Inn
9.4
Exceptional
287 reviews
View

Top Chatham Windmill Hotel Reviews

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

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

8/10 Good
"Great house, location was great also. Great yard for children to play. The biggest complaints are the master bedroom upstairs had a huge claw foot tub for shower, not suitable for seniors. The downstairs master bedroom had a ridiculous high bed impossible even for young couple to climb in with step. The lighting in the house was inadequate. We received a text reminding us to not have flood lights on after 10pm and be off the top deck by then which was no problem because we were always in way before then. Paul was very professional and recommended a great rental for sheets and bicycles."
Barbara T. 7-night trip
Posted 1 month ago
Water View-Walk town/beach, pets considered, Linen Option

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

Chase Park

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

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.
See properties

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 2.1 km 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 travellers, 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 5.1 km 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 travellers, 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 CA $95 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 trip 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 travellers' 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 1.8 km from Chatham Windmill, a travellers' 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 7.2 km from Chatham Windmill and is highly rated by travellers 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 travellers. 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 7.2 km 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 travellers.
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 travellers. With a lovely terrace and garden view restaurant, it offers a cozy atmosphere for travellers. 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 travellers, is a luxurious 5-star retreat located 7.2 km 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 travellers alike.Pleasant Bay Village ResortPleasant Bay Village Resort, a charming 3-star hotel located just 5.1 km from Chatham Windmill, offers travellers a warm, family-friendly atmosphere. With an impressive review rating of 9.6, travellers 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 travellers, 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 3.4 km from Chatham Windmill, is a fantastic option for budget-conscious travellers, rated 9.2 by travellers. 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 travellers 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 travellers' 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 7.2 km from Chatham Windmill, features a stunning array of boutique amenities and a remarkable travellers' rating of 9.4. This family-friendly resort boasts a children's club, babysitting services, and a poolside bar, ensuring a delightful stay for travellers 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 travellers 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 travellers. Rated 9.2 by travellers, 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 7.2 km from Chatham Windmill. With a fantastic review rating of 9.4, travellers 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 7.2 km from Chatham Windmill, with an impressive review rating of 9.4. This resort is ideal for travellers 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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