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Find hotels in Windsor, MA from CA $90

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Our top choices for Windsor hotels

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (837 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is CA $81
CA $90 total
includes taxes & fees
Jul 7 - Jul 8
FairBridge Inn Express

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (478 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is CA $96
CA $107 total
includes taxes & fees
Jul 28 - Jul 29
Berkshire Travel Lodge

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, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is CA $192
CA $215 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Plus Berkshire Hills Inn & Suites

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (920 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is CA $125
CA $147 total
includes taxes & fees
Jul 26 - Jul 27
Cozy Corner Motel

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is CA $181
CA $202 total
includes taxes & fees
Jul 7 - Jul 8
The Yankee Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (870 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is CA $112
CA $125 total
includes taxes & fees
Jul 6 - Jul 7
Berkshire Inn

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, (1,005 reviews)
"Clean room, great staff, parking"
United States
Gail
The price is CA $148
CA $165 total
includes taxes & fees
Jul 5 - Jul 6
Red Roof Inn PLUS+ South Deerfield – Amherst

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (671 reviews)
"Decent place.friendly, quiet"
United States
William
The price is CA $114
CA $127 total
includes taxes & fees
Jul 8 - Jul 9
Econo Lodge Lee - Great Barrington

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is CA $105
CA $115 total
includes taxes & fees
Jul 7 - Jul 8
Pleasant Valley Motel West Stockbridge

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (915 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is CA $142
CA $159 total
includes taxes & fees
Jul 6 - Jul 7
Howard Johnson by Wyndham Williamstown

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (795 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is CA $141
CA $157 total
includes taxes & fees
Jul 6 - Jul 7
The Villager Motel

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (35 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $235
CA $263 total
includes taxes & fees
Jul 8 - Jul 9
The Revival House

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $225
CA $247 total
includes taxes & fees
Jul 6 - Jul 7
Shaker Mill Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (418 reviews)
"Nice place for a stay"
United States
Jay
The price is CA $152
CA $170 total
includes taxes & fees
Jul 6 - Jul 7
Sunset Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is CA $201
CA $225 total
includes taxes & fees
Jul 6 - Jul 7
Quality Inn Lee - Lenox South

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is CA $127
CA $211 total
includes taxes & fees
Jul 6 - Jul 7
Blooming 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, (118 reviews)
The price is CA $243
CA $272 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (3 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is CA $254
CA $283 total
includes taxes & fees
Aug 2 - Aug 3
Berkshire Lake Lodge

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (251 reviews)
"Had a great stay."
United States
Trevor
The price is CA $114
CA $127 total
includes taxes & fees
Jul 20 - Jul 21
Rodeway Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (876 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is CA $141
CA $157 total
includes taxes & fees
Jul 20 - Jul 21
Howard Johnson by Wyndham Lenox
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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 $90 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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