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Aug 25 - Aug 26
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Compare 981 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₩175,230
₩195,731 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Wonderful place to stay"
The price is ₩173,086
₩193,342 total
includes taxes & fees
Sep 21 - Sep 22
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (695)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ₩222,259
₩248,264 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1973)
"Beautiful location!"
The price is ₩149,867
₩182,580 total
includes taxes & fees
Aug 28 - Aug 29
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1008)
"Great location!"
The price is ₩198,751
₩222,005 total
includes taxes & fees
Sep 24 - Sep 25
Hotel Downstreet, Ascend Hotel Collection
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ₩176,656
₩251,415 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (529)
"Great place , love it, will return"
The price is ₩201,947
₩225,575 total
includes taxes & fees
Sep 17 - Sep 18
The Constance by the Lenox Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (708)
"Pleasant stay"
The price is ₩126,611
₩160,744 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Wonderful old inn; chock full of charm."
The price is ₩275,332
₩369,360 total
includes taxes & fees
Sep 10 - Sep 11
The Red Lion Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (593)
"Amazing place to stay. Can’t wait to go again. "
The price is ₩106,197
₩149,532 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (865)
"Consistently a clean room with welcoming staff."
The price is ₩150,810
₩168,454 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (769)
"Close to our target event a plus"
The price is ₩98,373
₩109,884 total
includes taxes & fees
Sep 8 - Sep 9
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (24)
"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "
The price is ₩186,991
₩208,870 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (438)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is ₩93,378
₩104,585 total
includes taxes & fees
Sep 14 - Sep 15
Berkshire Travel Lodge
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (869)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is ₩152,180
₩169,987 total
includes taxes & fees
Aug 27 - Aug 28
Howard Johnson by Wyndham Williamstown
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (626)
"It was lovely!"
The price is ₩88,203
₩98,522 total
includes taxes & fees
Sep 9 - Sep 10
Econo Lodge Lee - Great Barrington
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (730)
"Great quiet stay. "
The price is ₩123,139
₩137,542 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Very clean rooms and excellent staff."
The price is ₩146,992
₩164,189 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is ₩123,277
₩137,700 total
includes taxes & fees
Sep 7 - Sep 8
Williamstown Motel
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1003)
"It’s the only place close to the Treehouse so we stayed there, it is definitely a RR Inn."
The price is ₩148,169
₩165,505 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn PLUS+ South Deerfield – Amherst
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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Learn more about Windsor

Explore Windsor: its food and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

The Constance by the Lenox Collection

The Constance by the Lenox Collection

10/10 Excellent
"We enjoyed our stay at the Whitlock (part of the same management as the Constance). Good restaurants easy to walk to. Quiet. Only thing we missed was a comfortable armchair in the bedroom."
James 1-night trip
Posted 13 hours ago
The Constance by the Lenox Collection

More cheap stays in Windsor

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is ₩109,303 per night from Sep 1 to Sep 2
₩109,303
₩122,087 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (785 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Berkshire Mountain Lodge and FairBridge Inn Express. 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.

Where can I learn more about changing or cancelling my trip to Windsor?

For more information about updating your trip to Windsor or cancelling it, click here.

What's the best hotel for staying near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 Mount Greylock State Reservation Visitor Center, Mount Greylock, and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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.