Find hotels in Windsor, MA from ฿2,451

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5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
7 Nov - 9 Nov
Next weekend
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, (1000)
"Good for one night stay"
United States
Marla
The price is ฿3,564
฿3,981 total
includes taxes & fees
5 Dec - 6 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (791)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is ฿3,011
฿3,363 total
includes taxes & fees
6 Nov - 7 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, (1030)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is ฿3,539
฿3,953 total
includes taxes & fees
6 Dec - 7 Dec
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, (941)
"Spotless and friendly staff"
United States
Nikisha
The price is ฿3,348
฿3,739 total
includes taxes & fees
7 Nov - 8 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, (2123)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is ฿2,981
฿3,686 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, (747)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
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, (1000)
"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 ฿4,186
฿5,946 total
includes taxes & fees
6 Nov - 7 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, (1000)
"Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again."
United States
Tammy
The price is ฿4,863
฿5,432 total
includes taxes & fees
16 Nov - 17 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, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is ฿3,849
฿4,299 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (778)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is ฿3,932
฿4,847 total
includes taxes & fees
6 Nov - 7 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (791)
"Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! "
United States
Ann
The price is ฿4,335
฿4,842 total
includes taxes & fees
6 Nov - 7 Nov
Hotel On North
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1028)
"Food was great!"
United States
Emily
The price is ฿4,843
฿6,861 total
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
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, (1057)
"Parking was great. Food in the area was good. Staff was nice. "
United States
Gabriel
The price is ฿2,778
฿3,104 total
includes taxes & fees
9 Nov - 10 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (806)
"Good service and people"
United States
Jerod
The price is ฿2,194
฿2,451 total
includes taxes & fees
18 Nov - 19 Nov
FairBridge Inn Express
Front of property – evening/night
The Williams Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (533)
"Great stay"
United States
SIDNEY
The price is ฿6,406
฿7,155 total
includes taxes & fees
17 Nov - 18 Nov
The Williams Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (338)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿3,674
฿4,104 total
includes taxes & fees
6 Nov - 7 Nov
The Central Downtown Inn & Suites
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 ฿2,893
฿3,231 total
includes taxes & fees
11 Nov - 12 Nov
Williamstown Motel
Exterior
Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
8.8 out of 10, Excellent, (391)
"We really liked the beautiful fire pit and the warm cup of tea after coming home from dinner."
United States
Kathleen
The price is ฿5,103
฿5,699 total
includes taxes & fees
11 Nov - 12 Nov
Fairfield Inn & Suites by Marriott Williamstown
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1025)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ฿3,038
฿3,394 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Plus Berkshire Hills Inn & Suites
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 ฿4,669
฿5,941 total
includes taxes & fees
4 Dec - 5 Dec
The Porches Inn at Mass MoCA
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We truly enjoyed our stay. Our room was spacious, beds comfy and the charm and history of the inn is truly enchanting. "
Lori 1-night trip
Posted 2 days ago
The Red Lion Inn

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 ฿2,778 per night from 9 Nov to 10 Nov
฿2,778
฿3,104 total
9 Nov - 10 Nov
includes taxes & fees
7/10 Good! (1,054 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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