Windsor Hotels

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Tonight
Nov 20 - Nov 21
Tomorrow
Nov 21 - Nov 22
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

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Top 10 trending Windsor hotels

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is P6,261
P6,994 total
includes taxes & fees
Dec 11 - Dec 12
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
The price is P5,360
P5,987 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (800)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is P5,460
P6,098 total
includes taxes & fees
Nov 23 - Nov 24
Berkshires Untold
Restaurant
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, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,198
P5,806 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2138)
"Great place!"
United States
Nicole
The price is P4,364
P5,521 total
includes taxes & fees
Nov 23 - Nov 24
Vacation Village in the Berkshires
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is P7,590
P10,782 total
includes taxes & fees
Nov 21 - Nov 22
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (762)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (786)
"Place was great!"
United States
Benjamin
The price is P6,276
P7,833 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is P5,846
P6,530 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1005)
"Staff was very nice!"
United States
David
The price is P7,937
P8,866 total
includes taxes & fees
Dec 18 - Dec 19
Hotel Downstreet, an Ascend Collection Hotel
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is P8,780
P12,441 total
includes taxes & fees
Dec 15 - Dec 16
The Red Lion Inn
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (798)
"Clean room and staff was super friendly"
United States
Yuen
The price is P7,861
P8,781 total
includes taxes & fees
Dec 7 - Dec 8
Hotel On North
Desk, laptop workspace, blackout drapes, iron/ironing board
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, (1004)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is P5,250
P5,864 total
includes taxes & fees
Nov 23 - Nov 24
Red Roof Inn PLUS+ South Deerfield – Amherst
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby sitting area
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, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is P5,509
P6,153 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Plus Berkshire Hills Inn & Suites
2 bedrooms, Frette Italian sheets, premium bedding, down comforters
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (438)
"It is the perfect place to stay!"
United States
Darrell
The price is P8,963
P11,328 total
includes taxes & fees
Dec 4 - Dec 5
The Porches Inn at Mass MoCA
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (392)
"our stay was great."
United States
nathaniel
The price is P8,427
P9,413 total
includes taxes & fees
Dec 7 - Dec 8
Fairfield Inn & Suites by Marriott Williamstown
Front of property - evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (544)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is P11,615
P12,974 total
includes taxes & fees
Nov 23 - Nov 24
The Williams Inn
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (761)
"It's very good for stay over"
United States
Frances
The price is P4,066
P4,542 total
includes taxes & fees
Dec 1 - Dec 2
The Villager Motel
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (345)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is P5,262
P5,878 total
includes taxes & fees
Nov 25 - Nov 26
The Central Downtown Inn & Suites
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 6 days ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
The price is P5,250 per night from Nov 23 to Nov 24
P5,250
P5,864 total
Nov 23 - Nov 24
includes taxes & fees
7/10 Good! (1,002 reviews)

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 traveler data. Other good options for your visit to the area are Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. 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! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given 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 accommodations 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 Wahconah Falls State Park, Crane Museum of Papermaking, and Mount Greylock State Reservation Visitor Center. You'll also find Swift River and Mount Greylock in the area. Check out what more to see and do in Expedia's Windsor guide.
What's the seasonal weather like in Windsor?
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.

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