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Find hotels in Windsor, MA from CA $97

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Our top choices for Windsor hotels

Historic Beaver Mill Inn

Historic Beaver Mill Inn
2.0 star property
North Adams
The price is CA $195
CA $218 total
includes taxes & fees
Aug 11 - Aug 12
Historic Beaver Mill Inn

Shelburne Springs

Shelburne Springs
2.0 star property
Shelburne
The price is CA $572
CA $639 total
includes taxes & fees
Jul 14 - Jul 15
Shelburne Springs

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,006 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is CA $169
CA $188 total
includes taxes & fees
Jul 15 - Jul 16
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is CA $214
CA $239 total
includes taxes & fees
Jul 13 - Jul 14
The Yankee Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (129 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is CA $223
CA $249 total
includes taxes & fees
Jul 16 - Jul 17
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (851 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is CA $87
CA $97 total
includes taxes & fees
Jul 27 - Jul 28
FairBridge Inn Express

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (36 reviews)
The price is CA $234
CA $262 total
includes taxes & fees
Jul 13 - Jul 14
The Revival House

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,003 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is CA $96
CA $105 total
includes taxes & fees
Jul 13 - Jul 14
Pleasant Valley Motel West Stockbridge

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (928 reviews)
"Very nice and cute place to stay. Staff was very friendly and helpful. Room was nice and clean. Very quiet with beautiful outside property. The only problem was no coffee or breakfast until 8am."
United States
Tracy
The price is CA $125
CA $147 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Corner Motel

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (490 reviews)
"We needed a bed for a quick crash session on the way through. The gentleman at the front desk was pleasant and so helpful and kind."
United States
Kyle
The price is CA $96
CA $107 total
includes taxes & fees
Jul 13 - Jul 14
Berkshire Travel Lodge

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,008 reviews)
"Clean and convenient!"
United States
Katie
The price is CA $140
CA $156 total
includes taxes & fees
Jul 20 - Jul 21
Red Roof Inn PLUS+ South Deerfield – Amherst

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (256 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
The price is CA $113
CA $127 total
includes taxes & fees
Jul 20 - Jul 21
Rodeway Inn

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (799 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is CA $140
CA $157 total
includes taxes & fees
Jul 15 - Jul 16
The Villager Motel

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (424 reviews)
"Nice place for a stay"
United States
Jay
The price is CA $156
CA $174 total
includes taxes & fees
Jul 20 - Jul 21
Sunset Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,012 reviews)
"Great place"
United States
Michelle
The price is CA $187
CA $209 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn Lee - Lenox South

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,009 reviews)
"Great value and excellent location"
United States
Truett
The price is CA $133
CA $149 total
includes taxes & fees
Jul 13 - Jul 14
Willows Motel Williamstown

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Great place"
United States
Luciane
The price is CA $140
CA $157 total
includes taxes & fees
Jul 13 - Jul 14
Howard Johnson by Wyndham Lenox

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (876 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is CA $127
CA $142 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Inn

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (17 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is CA $187
CA $209 total
includes taxes & fees
Jul 15 - Jul 16
Hideaway Inn Lenox

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (331 reviews)
"Clean rooms and the staff was extremely friendly and helpful"
United States
Graham
The price is CA $123
CA $138 total
includes taxes & fees
Jul 15 - Jul 16
Williamstown Motel
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Top Windsor Hotel Reviews

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Frequently asked questions

What is the best area to stay in Windsor?
The best area to stay in Windsor is the main town centre, particularly around the historic Market Square and along Peascod Street.

This central area is the heart of Windsor, offering easy pedestrian access to many of the town's key attractions. You'll find a wide selection of shops, restaurants, and pubs here, all within a short stroll of Windsor Castle and the Long Walk. The streets are generally well-kept and easy to navigate.

Couples looking for a romantic getaway will find the town centre ideal. With the castle on your doorstep, charming cobbled streets, and a variety of dining options from casual to fine dining, it provides a refined and convenient base for exploring. You can easily spend your days touring the castle, enjoying a boat trip on the River Thames, or simply relaxing in one of the many cafes.

Families will also appreciate the convenience of staying in the town centre. Being close to the castle means less travel time with little ones, and there are several parks nearby, including Alexandra Gardens along the river, superb for children to play.
When is the best time to go to Windsor?
The best time to go to Windsor, Massachusetts, is during the summer months, from June to August, and the early autumn, specifically September and October.

Summer offers warm, pleasant weather, ideal for outdoor activities like hiking, fishing, and exploring the natural beauty of the Berkshire Mountains. The days are long, allowing ample time for sightseeing and enjoying the region's lakes and rivers. This is a great time for families looking for a relaxed holiday with plenty of fresh air and nature.

Early autumn brings cooler temperatures and the spectacular colours of the fall foliage. This period is particularly good for couples or solo travellers who appreciate scenic drives, photography, and outdoor adventures in a picturesque setting.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor.
How can I save on a Windsor hotel booking with Expedia?
Members always get our best prices. Find our best Windsor hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Windsor hotel?
Prices for hotels in Windsor often vary, but you can find a great deal from CA $97 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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