A windmill, a boat, and a beach.

Find hotels near Chatham Windmill, Chatham from $211

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chatham Windmill hotels

1. Old Harbor Inn

Old Harbor Inn
3.5 star property
0.5 mi from Chatham Windmill
9.6 out of 10, Exceptional, (166 reviews)
"We loved staying here. Everything is pristine and clean. The breakfast was delicious - the blueberry pancakes likely the best I’ve had in my life. Very walkable to everything on Main Street. Easy to drive to other beaches further up north. The staff are professional and attentive - what a pleasure."
United States
Kazuho
$558 nightly
The price is $638
Aug 12 - Aug 13
Total with taxes and fees
Old Harbor Inn

2. Chatham Bars Inn

Chatham Bars Inn
5.0 star property
0.7 mi from Chatham Windmill
9.2 out of 10, Wonderful, (845 reviews)
"Beautiful Cape Cod style Inn with every amenity you could want. Restaurants all had great menu selections"
United States
Mark
$1,045 nightly
The price is $1,196
Aug 2 - Aug 3
Total with taxes and fees
Chatham Bars Inn

3. The Chatham Motel

The Chatham Motel
2.0 star property
1.6 mi from Chatham Windmill
9.2 out of 10, Wonderful, (633 reviews)
"Staff were super friendly and helpful and the room was super clean and perfect for what we needed. Can't recommend this place enough! "
United States
Christopher
$341 nightly
The price is $390
Jul 22 - Jul 23
Total with taxes and fees
The Chatham Motel

4. Queen Anne Inn

Queen Anne Inn
4.0 star property
0.7 mi from Chatham Windmill
8.8 out of 10, Excellent, (253 reviews)
"Great breakfast, nice pool area"
United States
David
$245 nightly
The price is $280
Aug 5 - Aug 6
Total with taxes and fees
Queen Anne Inn

5. Candleberry Inn on Cape Cod

Candleberry Inn on Cape Cod
4.5 star property
8.7 mi from Chatham Windmill
10.0 out of 10, Exceptional, (142 reviews)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
United States
Michelle
$370 nightly
The price is $423
Jul 30 - Jul 31
Total with taxes and fees
Candleberry Inn on Cape Cod

6. Captain Freeman Inn

Captain Freeman Inn
4.0 star property
8.7 mi from Chatham Windmill
10.0 out of 10, Exceptional, (70 reviews)
"Lovely house with delicious breakfast and very welcoming hosts. Spacious room with heavenly sheets on a very comfortable bed. "
United States
Robert
$405 nightly
The price is $464
Aug 4 - Aug 5
Total with taxes and fees
Captain Freeman Inn

7. Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod
3.0 star property
9.2 mi from Chatham Windmill
9.8 out of 10, Exceptional, (447 reviews)
"staff were so so friendly! and the complimentary breakfast was really yummy too! Would definitely stay here again if we were in the area"
United States
Rachel
$203 nightly
The price is $232
Jul 22 - Jul 23
Total with taxes and fees
Eagle Wing Inn - Cape Cod

8. Pleasant Bay Village Resort

Pleasant Bay Village Resort
3.0 star property
2.8 mi from Chatham Windmill
9.6 out of 10, Exceptional, (321 reviews)
"Loved our recent stay ! This hotel Is so private and nice! My tweens loved the pool and feeding the koi fish everyday! Loved easy access of ordering poolside lunch and just a quick drive to Main Street for shopping. What a gem of a hotel-we will def be back! Thank you for such a great staff! Staff was so polite and helpful"
United States
Allison
$296 nightly
The price is $339
Aug 5 - Aug 6
Total with taxes and fees
Pleasant Bay Village Resort

9. The Old Manse Inn

The Old Manse Inn
4.5 star property
8.7 mi from Chatham Windmill
9.8 out of 10, Exceptional, (253 reviews)
"Lovely place to stay. Breakfast was delicious!"
United States
Roberta
$328 nightly
The price is $375
Jul 29 - Jul 30
Total with taxes and fees
The Old Manse Inn

10. The Captain Farris House B&B

The Captain Farris House B&B
3.5 star property
11.8 mi from Chatham Windmill
9.8 out of 10, Exceptional, (265 reviews)
"Had a wonderful stay and Carol and the staff were so delightful. It was a great experience. Highly recommend!"
United States
Laura
$301 nightly
The price is $343
Aug 4 - Aug 5
Total with taxes and fees
The Captain Farris House B&B

11. Charm on Main by Ocean Edge

Charm on Main by Ocean Edge
2.0 star property
8.2 mi from Chatham Windmill
9.6 out of 10, Exceptional, (21 reviews)
$357 nightly
The price is $408
Aug 2 - Aug 3
Total with taxes and fees
Charm on Main by Ocean Edge

12. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
2.5 star property
7.6 mi from Chatham Windmill
9.4 out of 10, Exceptional, (265 reviews)
"This place is very cute, clean, well maintained and quiet. We really enjoyed our stay here"
United States
Sheryl
$195 nightly
The price is $223
Jul 23 - Jul 24
Total with taxes and fees
Olde Tavern Motel And Inn

13. Doryman Motel

Doryman Motel
2.0 star property
9.1 mi from Chatham Windmill
9.6 out of 10, Exceptional, (130 reviews)
"Great place to stay. Close to the beach in a quiet neighborhood. Rooms are very clean!"
United States
Brian
$230 nightly
The price is $263
Jul 26 - Jul 27
Total with taxes and fees
Doryman Motel

14. Pelham on Earle

Pelham on Earle
3.0 star property
7.3 mi from Chatham Windmill
9.6 out of 10, Exceptional, (88 reviews)
"Great place the roof top bar restaurant was beautiful "
United States
Maryellen
$406 nightly
The price is $465
Jul 26 - Jul 27
Total with taxes and fees
Pelham on Earle

15. Chatham Tides

Chatham Tides
2.5 star property
3.9 mi from Chatham Windmill
9.4 out of 10, Exceptional, (731 reviews)
"Beautiful location and great amenities. Staff were super helpful and the room was everything we needed for a great stay."
United States
Pamela
$512 nightly
The price is $586
Aug 17 - Aug 18
Total with taxes and fees
Chatham Tides

16. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
3.0 star property
9.2 mi from Chatham Windmill
9.6 out of 10, Exceptional, (16 reviews)
"We stayed here over Memorial Day weekend with our dog and toddler, the place is really nice! Clearly recently renovated, rooms were well kept, great location on the cape. Would recommend!"
United States
Brandon
$212 nightly
The price is $243
Jul 22 - Jul 23
Total with taxes and fees
Dennis Port Surf Club (Boutique Hotel)

17. Sesuit Harbor House

Sesuit Harbor House
3.0 star property
11.7 mi from Chatham Windmill
9.6 out of 10, Exceptional, (194 reviews)
"Had a great time, close to great beaches, pool and activities for the kids, helpful staff. Will def be back !!"
United States
Marisa
$324 nightly
The price is $371
Jul 27 - Jul 28
Total with taxes and fees
Sesuit Harbor House

18. The Escape Inn

The Escape Inn
2.5 star property
12.1 mi from Chatham Windmill
9.4 out of 10, Exceptional, (726 reviews)
"We stayed for one night at the Escape Inn and thought it was great. Check in was easy, the room was very clean and the bed was comfortable. The property was quiet and pretty. Parking was free and easy and we enjoyed a swim in the pool. We did not partake in the free breakfast so I can't comment on that but all in all we enjoyed our stay and would come again!"
United States
Anne
$184 nightly
The price is $211
Jul 23 - Jul 24
Total with taxes and fees
The Escape Inn

19. Skaket Beach Motel

Skaket Beach Motel
2.0 star property
7.5 mi from Chatham Windmill
9.2 out of 10, Wonderful, (477 reviews)
"This is probably the nicest motel I have ever stayed at. I especially appreciate the gardens and planting throughout the property, and a quiet room despite being near a busy intersection."
United States
Richard
$220 nightly
The price is $252
Jul 22 - Jul 23
Total with taxes and fees
Skaket Beach Motel

20. Kingfisher Oceanside

Kingfisher Oceanside
2.0 star property
9.2 mi from Chatham Windmill
9.2 out of 10, Wonderful, (188 reviews)
"Very great stay, staff if very kind and accommodating, room was very clean super close to the beach."
United States
David
$244 nightly
The price is $279
Jul 22 - Jul 23
Total with taxes and fees
Kingfisher Oceanside
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.

Compare popular hotels close to Chatham Windmill

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Hiking
Old Harbor Inn
3.5 star property
9.6
Exceptional
166 reviews
View
Exterior
Chatham Bars Inn
5.0 star property
9.2
Wonderful
845 reviews
View
Superior Room, 2 Double Beds, Kitchenette | Private kitchen | Coffee/tea maker, fridge
The Chatham Motel
2.0 star property
9.2
Wonderful
633 reviews
View
Seasonal outdoor pool, pool umbrellas, sun loungers
Queen Anne Inn
4.0 star property
8.8
Excellent
253 reviews
View
Exterior detail
Candleberry Inn on Cape Cod
4.5 star property
10.0
Exceptional
142 reviews
View

Top Chatham Windmill Hotel Reviews

Hotels near other Chatham Windmill attractions

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 Inn

Captain'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 Inn

Old 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 Resort

Pleasant 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 Inn

Old 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 Hawthorne

The 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 Inn

Chatham 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 $211 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 Inn

Chatham 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 Inn

Greyfinch 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 Club

Wequassett 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 Inn

Chatham 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 Club

Wequassett 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 Inn

Chatham 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 Inn

Chatham 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 Club

Wequassett 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 Resort

Pleasant 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 Hawthorne

The 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 Motel

The 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 Inn

Chatham 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 Club

Wequassett 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 Inn

Chatham 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 Inn

Just 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 Club

Wequassett 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 Club

Wequassett 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.

Explore a world of travel with Expedia