Hotels near Chatham Windmill

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chatham Windmill hotels

Beach nearby
Chatham Wayside Inn

Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
0.5 km from Chatham Windmill
9.2 out of 10, Wonderful, (609)
"Yes, lovely place to stay."
United States
Angela
Chatham Wayside Inn
Seasonal outdoor pool
Chatham Bars Inn

Chatham Bars Inn

Chatham Bars Inn
5.0 star property
1.1 km from Chatham Windmill
9.2 out of 10, Wonderful, (799)
"Helpful staff & food & drinks were great ! "
United States
glen
The price is P22,215
P26,697 total
includes taxes & fees
Dec 29 - Dec 30
Chatham Bars Inn
Beach/ocean view
Nauset Beach Inn

Nauset Beach Inn

Nauset Beach Inn
3.0 star property
12.5 km from Chatham Windmill
9.4 out of 10, Exceptional, (175)
"very accommodating. Great location. Loved my stay!"
United States
Peter
The price is P13,508
P16,464 total
includes taxes & fees
Dec 29 - Dec 30
Nauset Beach Inn
Property grounds
The Escape Inn

The Escape Inn

The Escape Inn
2.5 star property
19.5 km from Chatham Windmill
9.4 out of 10, Exceptional, (658)
"Great place"
United States
Karim
The price is P5,272
P6,035 total
includes taxes & fees
Dec 28 - Dec 29
The Escape Inn
Gazebo
Veranda Cape Cod Family Resort

Veranda Cape Cod Family Resort

Veranda Cape Cod Family Resort
2.5 star property
19.4 km from Chatham Windmill
9.2 out of 10, Wonderful, (262)
"Beautiful grounds, quiet and comfortable. Very well run. "
United States
Benita
The price is P10,513
P12,032 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Veranda Cape Cod Family Resort
Premium bedding, minibar, blackout drapes, iron/ironing board
Pelham House Resort

Pelham House Resort

Pelham House Resort
2.5 star property
14.8 km from Chatham Windmill
8.6 out of 10, Excellent, (204)
"Excellent location and the room was stunning! "
United States
james
The price is P10,983
P13,827 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Pelham House Resort
Indoor pool, seasonal outdoor pool, sun loungers
Ambassador Inn & Suites

Ambassador Inn & Suites

Ambassador Inn & Suites
3.0 star property
19 km from Chatham Windmill
8.6 out of 10, Excellent, (629)
"I love staying here. "
United States
Jacqueline
Ambassador Inn & Suites
Terrace/patio
The Mansion at Ocean Edge

The Mansion at Ocean Edge

The Mansion at Ocean Edge
4.0 star property
13.3 km from Chatham Windmill
8.2 out of 10, Very Good, (1000)
"The hotel is beautifully decorated for the holiday season"
United States
Mary
The price is P9,348
P14,060 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Mansion at Ocean Edge
Fitness facility
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham
3.0 star property
19.6 km from Chatham Windmill
8.4 out of 10, Very Good, (306)
"My room was very clean. The staff were friendly."
United States
Shanique
The price is P5,022
P6,553 total
includes taxes & fees
Jan 4 - Jan 5, 2026
All Seasons Resort, Trademark Collection by Wyndham
Premium bedding, desk, iron/ironing board, rollaway beds
Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
2.0 star property
13.2 km from Chatham Windmill
8.0 out of 10, Very Good, (788)
"Clean and comfortable room very enjoyable stay"
United States
Douglas
The price is P6,167
P7,058 total
includes taxes & fees
Dec 28 - Dec 29
Rodeway Inn Orleans - Cape Cod
Indoor pool, seasonal outdoor pool
Four Points by Sheraton Eastham Cape Cod

Four Points by Sheraton Eastham Cape Cod

Four Points by Sheraton Eastham Cape Cod
3.0 star property
19 km from Chatham Windmill
8.2 out of 10, Very Good, (860)
"Perfect overnight stay in every way!"
United States
Debra
The price is P6,930
P7,932 total
includes taxes & fees
Dec 30 - Dec 31
Four Points by Sheraton Eastham Cape Cod
Front of property
Jonathan Edwards Motel

Jonathan Edwards Motel

Jonathan Edwards Motel
2.0 star property
14.5 km from Chatham Windmill
6.6 out of 10, (46)
"It’s was a really great place to stay and very clean. The staff was very nice we will return again"
United States
Joe
The price is P5,233
P5,989 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Jonathan Edwards Motel
Terrace/patio
An English Garden Bed & Breakfast

An English Garden Bed & Breakfast

An English Garden Bed & Breakfast
3.0 star property
13.7 km from Chatham Windmill
9.0 out of 10, Wonderful, (60)
"A charming hotel a block away from a nice sandy beach, loved a stay there."
United States
Hwamee
The price is P11,306
P14,621 total
includes taxes & fees
Jan 1 - Jan 2, 2026
An English Garden Bed & Breakfast
Private kitchen
Brewster Green Resort

Brewster Green Resort

Brewster Green Resort
2.5 star property
12 km from Chatham Windmill
The price is P41,112
P47,053 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Brewster Green Resort
3 bedrooms, desk
Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
16.6 km from Chatham Windmill
The price is P20,752
P49,027 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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.
View all properties

Top Chatham Windmill Hotel Reviews

Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"An incredible stay. Room at the main inn could use some updating. Just a bit tired with cracked tiles and some worn furniture, but overall the hotel is spectacular. The breakfast at Stars was amazing. "
Kyle 2-night trip
Posted 11 days ago
Chatham Bars Inn

Hotels near other Chatham Windmill attractions

Chatham Light is a lighthouse located in Chatham, Massachusetts. Built in 1808 is a popular landmark in Cape Cod,and easily accessible by car. #BVSBlue
Photo by Donny Campos
Open Photo by Donny Campos

Chatham Lighthouse

4.6/5 (96 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.
See properties
Summer Baseball Game at Chatham, Cape Cod League

Veterans Field

Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.
See properties

Frequently asked questions

What's the area like around Chatham Windmill?
Chatham Windmill is located in a trendy area of Chatham known for its top seafood restaurants and sporting events. If you're looking for a convenient place to stay, check out the 154 hotels and other accommodations you'll find within a mile.
What's the best place to stay near Chatham Windmill?
Adjacent to Chatham Windmill, Chatham Wayside Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. Other good options within a short distance include Chatham Bars Inn and Surfside Inn Chatham.
How many hotels will I find close to Chatham Windmill?
Expedia has 154 hotels and other accommodations within a mile from Chatham Windmill.
If I need to cancel the hotel reservation for my stay near Chatham Windmill, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to review top deals close to Chatham Windmill.
What can I see and do near Chatham Windmill?
You'll want to browse the collections at Chatham Shark Center, Atwood House Museum, and Chatham Railroad Museum. Some landmarks that you won't want to miss include Chatham Lighthouse, Chatham Lighthouse Beach, and Mayo House. You can enjoy live performances at Monomoy Theatre and Chatham Drama Guild.