Find hotels near Chatham Windmill, Chatham

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Compare hotels close to Chatham Windmill with room rates, reviews, and availability. Most hotels are fully refundable.

Chatham Wayside Inn

4.0 star property
0.3 mi from Chatham Windmill
9.2 out of 10, Wonderful, (592)
"We loved staying here! Our room was spacious, clean, quiet and very well maintained. The hotel is beautiful and a perfect location. "
United States
Beth
$174 nightly
The price is $199
Nov 24 - Nov 25
Total with taxes and fees
Chatham Wayside Inn

Chatham Tides

2.5 star property
3.8 mi from Chatham Windmill
9.4 out of 10, Exceptional, (661)
"We loved it so much that we will definitely going back. "
United States
Faith
$152 nightly
The price is $174
Dec 8 - Dec 9
Total with taxes and fees
Chatham Tides

Jonathan Edwards Motel

2.0 star property
9 mi from Chatham Windmill
6.6 out of 10, (45)
"It’s was a really great place to stay and very clean. The staff was very nice we will return again"
United States
Joe
$83 nightly
The price is $96
Nov 30 - Dec 1
Total with taxes and fees
Jonathan Edwards Motel

Nauset Beach Inn

3.0 star property
7.8 mi from Chatham Windmill
9.4 out of 10, Exceptional, (175)
"very accommodating. Great location. Loved my stay!"
United States
Peter
$245 nightly
The price is $280
Nov 24 - Nov 25
Total with taxes and fees
Nauset Beach Inn

Candleberry Inn on Cape Cod

4.5 star property
8.7 mi from Chatham Windmill
10.0 out of 10, Exceptional, (139)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
United States
Michelle
$309 nightly
The price is $354
Nov 24 - Nov 25
Total with taxes and fees
Candleberry Inn on Cape Cod

Rodeway Inn Orleans - Cape Cod

2.0 star property
8.2 mi from Chatham Windmill
8.0 out of 10, Very Good, (784)
"Clean and comfortable room very enjoyable stay"
United States
Douglas
$105 nightly
The price is $120
Nov 24 - Nov 25
Total with taxes and fees
Rodeway Inn Orleans - Cape Cod

The Mansion at Ocean Edge

4.0 star property
8.2 mi from Chatham Windmill
8.2 out of 10, Very Good, (1000)
"Amazing stay and location! "
United States
Joanne
$255 nightly
The price is $283
Nov 24 - Nov 25
Total with taxes and fees
The Mansion at Ocean Edge

Pelham House Resort

2.5 star property
9.2 mi from Chatham Windmill
8.6 out of 10, Excellent, (198)
"Wonderful stay "
United States
jennifer
$161 nightly
The price is $184
Dec 23 - Dec 24
Total with taxes and fees
Pelham House Resort

The Escape Inn

2.5 star property
12.1 mi from Chatham Windmill
9.4 out of 10, Exceptional, (648)
"One of the best hotels I stayed at "
United States
Robert
$90 nightly
The price is $103
Nov 24 - Nov 25
Total with taxes and fees
The Escape Inn

Ambassador Inn & Suites

3.0 star property
11.8 mi from Chatham Windmill
8.6 out of 10, Excellent, (628)
"I love staying here. "
United States
Jacqueline
$108 nightly
The price is $122
Nov 24 - Nov 25
Total with taxes and fees
Ambassador Inn & Suites

All Seasons Resort, Trademark Collection by Wyndham

3.0 star property
12.2 mi from Chatham Windmill
8.4 out of 10, Very Good, (301)
"My room was very clean. The staff were friendly."
United States
Shanique
$103 nightly
The price is $118
Nov 24 - Nov 25
Total with taxes and fees
All Seasons Resort, Trademark Collection by Wyndham

Four Points by Sheraton Eastham Cape Cod

3.0 star property
11.8 mi from Chatham Windmill
8.2 out of 10, Very Good, (851)
"Perfect overnight stay in every way!"
United States
Debra
$118 nightly
The price is $135
Dec 23 - Dec 24
Total with taxes and fees
Four Points by Sheraton Eastham Cape Cod

Coastal Haven in West Dennis -15

2.0 star property
10.3 mi from Chatham Windmill
$725 nightly
The price is $850
Dec 6 - Dec 7
Total with taxes and fees
Coastal Haven in West Dennis -15
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.

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 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.
Can I find Expedia discounts for hotels near Chatham Windmill?
To look for discounts on hotels near Chatham Windmill, join One Key™—our free travel rewards program. One Key members always get our best prices and earn OneKeyCash™* on eligible bookings for every dollar spent. Another way to save is by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Explore a world of travel with Expedia