Find Cheap Hotels in Windsor, MA

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Our top choices for Windsor cheap hotels

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is NT$3,143
NT$3,510 total
includes taxes & fees
May 27 - May 28
Berkshires Untold

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (135 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is NT$3,165
NT$5,074 total
includes taxes & fees
May 27 - May 28
Blooming Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is NT$3,519
NT$3,860 total
includes taxes & fees
May 11 - May 12
Shaker Mill Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is NT$5,244
NT$5,858 total
includes taxes & fees
May 20 - May 21
Element Lenox Berkshires

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is NT$5,417
NT$6,050 total
includes taxes & fees
May 11 - May 12
The Revival House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is NT$2,755
NT$3,778 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain 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, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is NT$3,452
NT$3,856 total
includes taxes & fees
May 13 - May 14
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is NT$3,109
NT$3,472 total
includes taxes & fees
May 12 - May 13
The Yankee 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, (1,006 reviews)
"Was great room was clean staff was nice"
United States
Theresa
The price is NT$3,424
NT$3,825 total
includes taxes & fees
May 31 - Jun 1
Red Roof Inn PLUS+ South Deerfield – Amherst

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,004 reviews)
"Great location "
United States
Edith
The price is NT$3,467
NT$3,872 total
includes taxes & fees
May 19 - May 20
Quality Inn Lee - Lenox South
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 Windsor Hotel Reviews

Frequently asked questions

What is Windsor like for travelers on a budget?
Discover discount places to stay in Windsor on Expedia.com and book a trip that stays within your budget. You can browse a wide selection of hotels and other types of accommodation with Member Prices to find the best deal for you. With our site's helpful page filters, you can limit results by price per night, or by amenities that customers often look for like free breakfast and a swimming pool. If you're interested in affordable options near specific attractions, try filtering by location to refine your search. As you browse, click the heart button to save your favorites so that it's easy to find them when you're ready to book. Need a flight or a rental car along with your hotel? Choose from the Bundle and Save travel packages and discover huge discounts by reserving transportation at the same time.
When is the best time for a budget trip to Windsor?
Weather will likely play an important role when you plan your trip to Windsor, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to see and do in Windsor?
You don't need to spend a fortune to find things to see and do in Windsor. You can budget for the local attractions that interest you most, and then plan some activities that cost very little. Check out the local culture at Susan B. Anthony Birthplace Museum and Barrington Stage Company, or visit other spots like Berkshire Museum.
How can I get to Windsor and get around on a budget?
Scoping out the transportation options in Windsor can help keep you on budget. The closest airport is 13.8 mi (22.2 km) away from the center in Pittsfield, MA (PSF-Pittsfield Municipal). However, if that doesn't suit your budget, you can book a flight to Westfield, MA (BAF-Barnes Municipal), located 28.9 mi (46.5 km) away. Windsor might not have many public transit choices so a car rental could be a reasonable alternative to see more of the area.

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