Find hotels in Windsor, MA from ฿2,438

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1 Nov - 2 Nov
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2 Nov - 3 Nov
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7 Nov - 9 Nov
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14 Nov - 16 Nov

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Top 10 Windsor hotels and places to stay

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1002)
"We had a lakeside room which was wonderful!"
United States
Nancy
The price is ฿3,545
฿3,960 total
includes taxes & fees
10 Nov - 11 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (787)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is ฿2,995
฿3,346 total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1025)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is ฿3,463
฿3,868 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (935)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ฿3,330
฿3,720 total
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2117)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is ฿2,966
฿3,667 total
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (742)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1002)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
The price is ฿4,164
฿5,915 total
includes taxes & fees
2 Nov - 3 Nov
The Cornell Inn, Lenox & The Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1004)
"Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are."
United States
Robert
The price is ฿4,826
฿5,391 total
includes taxes & fees
9 Nov - 10 Nov
Hotel Downstreet, an Ascend Collection Hotel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is ฿3,820
฿4,267 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (788)
"Clean modern place in town, good value. Room on street side was a little noisy at night, ask for back room if light sleeper. Restaurant was not good value. "
United States
Michael
The price is ฿4,312
฿4,817 total
includes taxes & fees
17 Nov - 18 Nov
Hotel On North
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
9.0 out of 10, Wonderful, (773)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is ฿3,783
฿4,677 total
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1026)
"Food was great!"
United States
Emily
The price is ฿4,817
฿6,825 total
includes taxes & fees
13 Nov - 14 Nov
The Red Lion Inn
Front of property – evening/night
The Williams Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (532)
"Great stay"
United States
SIDNEY
The price is ฿6,372
฿7,118 total
includes taxes & fees
17 Nov - 18 Nov
The Williams Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (803)
"Good service and people"
United States
Jerod
The price is ฿2,182
฿2,438 total
includes taxes & fees
16 Nov - 17 Nov
FairBridge Inn Express
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (334)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is ฿3,655
฿4,082 total
includes taxes & fees
3 Nov - 4 Nov
The Central Downtown Inn & Suites
Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
7.2 out of 10, Good, (1049)
"Parking was great. Food in the area was good. Staff was nice. "
United States
Gabriel
The price is ฿2,764
฿3,087 total
includes taxes & fees
5 Nov - 6 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (558)
"I liked the old world decor and the living room area to chill out in "
United States
Jelena
The price is ฿4,059
฿4,534 total
includes taxes & fees
4 Nov - 5 Nov
The Constance by the Lenox Collection
Exterior detail
Williamstown Motel
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (309)
"It was clean and in a convenient location "
United States
Karen
The price is ฿3,201
฿3,575 total
includes taxes & fees
2 Nov - 3 Nov
Williamstown Motel
Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (432)
"Excellent place! "
United States
Francisco
The price is ฿5,194
฿6,524 total
includes taxes & fees
30 Nov - 1 Dec
The Porches Inn at Mass MoCA
Exterior
Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (390)
"We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner."
United States
Kathleen
The price is ฿5,076
฿5,670 total
includes taxes & fees
5 Nov - 6 Nov
Fairfield Inn & Suites by Marriott Williamstown
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

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

10/10 Excellent
"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "
Mona 3-night trip
Posted 5 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 ฿2,764 per night from 5 Nov to 6 Nov
฿2,764
฿3,087 total
5 Nov - 6 Nov
includes taxes & fees
7/10 Good! (1,045 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 traveller data. Other good options for your visit to the area are Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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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