Find hotels in Windsor, MA from ฿2,235

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Our top choices for Windsor hotels

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ฿13,461
฿14,767 total
includes taxes & fees
20 Mar - 21 Mar
Inn at Kenmore Hall

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (358 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿3,136
฿3,503 total
includes taxes & fees
11 Mar - 12 Mar
The Central Downtown Inn & Suites

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (203 reviews)
"Great stay! "
United States
ALEKSey
The price is ฿5,758
฿6,086 total
includes taxes & fees
11 Mar - 12 Mar
Blue Vista Motor Lodge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (846 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ฿2,724
฿3,042 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Inn

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)
"Very friendly and good Breakfast."
United States
Jesse
The price is ฿3,547
฿3,962 total
includes taxes & fees
15 Mar - 16 Mar
Best Western Plus Berkshire Hills Inn & Suites

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (672 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ฿4,050
฿4,524 total
includes taxes & fees
15 Mar - 16 Mar
Hilton Garden Inn Lenox Pittsfield

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (459 reviews)
"Location, hospitality, breakfast"
United States
Terry
The price is ฿4,818
฿6,089 total
includes taxes & fees
11 Mar - 12 Mar
The Porches Inn at Mass MoCA

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (838 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is ฿2,186
฿2,441 total
includes taxes & fees
12 Mar - 13 Mar
Howard Johnson by Wyndham Lenox

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is ฿4,719
฿5,286 total
includes taxes & fees
16 Mar - 17 Mar
Inn at Silver Maple Farm

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (830 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is ฿4,719
฿5,272 total
includes taxes & fees
15 Mar - 16 Mar
Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ฿4,023
฿4,493 total
includes taxes & fees
31 Mar - 1 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ฿15,647
฿17,478 total
includes taxes & fees
6 Apr - 7 Apr
33 Main

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "
United States
Cameron
The price is ฿1,995
฿2,235 total
includes taxes & fees
12 Mar - 13 Mar
Berkshire Travel Lodge

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ฿4,719
฿5,272 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (870 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is ฿3,368
฿4,470 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Mountain Lodge

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is ฿3,009
฿4,422 total
includes taxes & fees
1 Apr - 2 Apr
Becket Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (85 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is ฿4,181
฿4,670 total
includes taxes & fees
22 Mar - 23 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ฿8,036
฿8,494 total
includes taxes & fees
18 Mar - 19 Mar
Harbour House 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, (1,004 reviews)
"Really nice place staff "
United States
Omayra
The price is ฿2,680
฿2,993 total
includes taxes & fees
1 Apr - 2 Apr
Red Roof Inn PLUS+ South Deerfield – Amherst

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
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.
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Top Windsor Hotel Reviews

More cheap stays in Windsor

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Berkshire Mountain Lodge and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
What is staying in Windsor like?
Visitors can enjoy all that Windsor has to offer, including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodation options to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
Places to visit in the wider area include Mount Greylock State Reservation Visitor Center, Swift River and Mount Greylock. You'll also find Berkshire Athenaeum and Berkshire Museum in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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