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Find hotels in Windsor, MA from ฿2,282

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Check prices for these dates

Tonight
10 Sep - 11 Sep
Tomorrow
11 Sep - 12 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

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Our top choices for Windsor hotels

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
฿3,883
฿4,337 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Prasanna
฿3,481
฿3,888 total
includes taxes & fees
13 Sept - 14 Sept
Best Western Plus Berkshire Hills Inn & Suites

3. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Basil
฿4,727
฿5,280 total
includes taxes & fees
21 Sept - 22 Sept
Hotel Downstreet, an Ascend Collection Hotel

4. Hotel On North

Hotel On North
Pittsfield
United States
Drew
฿4,417
฿4,934 total
includes taxes & fees
13 Sept - 14 Sept
Hotel On North

5. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
Horace
฿2,043
฿2,282 total
includes taxes & fees
17 Sept - 18 Sept
FairBridge Inn Express

6. The Revival House

The Revival House
Adams
United States
James
฿5,449
฿6,087 total
includes taxes & fees
13 Sept - 14 Sept
The Revival House

7. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
฿3,817
฿4,264 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
฿4,813
฿5,377 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Sarah
฿3,131
฿3,858 total
includes taxes & fees
15 Sept - 16 Sept
Vacation Village in the Berkshires

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
irene
฿2,599
฿2,904 total
includes taxes & fees
13 Sept - 14 Sept
Howard Johnson by Wyndham Lenox

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Steve
฿4,015
฿4,484 total
includes taxes & fees
15 Sept - 16 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

12. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
฿6,573
฿7,342 total
includes taxes & fees
1 Oct - 2 Oct
Courtyard by Marriott Lenox Berkshires

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
฿4,506
฿5,033 total
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn & Suites Berkshires-Lenox

14. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Janis
฿2,902
฿3,411 total
includes taxes & fees
16 Sept - 17 Sept
Cozy Corner Motel

15. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
฿3,328
฿3,718 total
includes taxes & fees
30 Sept - 1 Oct
Quality Inn Lee - Lenox South

16. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
฿8,348
฿8,824 total
includes taxes & fees
21 Sept - 22 Sept
Harbour House Inn

17. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Chris
฿3,407
฿3,806 total
includes taxes & fees
21 Sept - 22 Sept
Willows Motel Williamstown

18. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
฿3,739
฿4,102 total
includes taxes & fees
13 Sept - 14 Sept
The Springs Motel

19. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Christine
฿4,113
฿4,595 total
includes taxes & fees
14 Sept - 15 Sept
Maple Terrace Motel

20. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
Williamstown
United States
Donna
฿3,619
฿4,043 total
includes taxes & fees
14 Sept - 15 Sept
Howard Johnson by Wyndham Williamstown
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Top Windsor Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"beautiful place, great staff, would love to go back!"
Sam 1-night trip
Posted 11 hours ago
Berkshires Untold
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"Room was clean and comfortable."
Mark 2-night trip
Posted 23 hours ago
FairBridge Inn Express
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Joanne 2-night trip
Posted 1 day ago
The Yankee Inn
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Awesome staff plus pet-friendly."
Gina 1-night trip
Posted 2 days ago
Willows Motel Williamstown
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Kimberly 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Michael 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Williams Inn

The Williams Inn

10/10 Excellent
"Exceptional hotel. Friendly vibe."
Silvia 1-night trip
Posted 2 days ago
The Williams Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
Mary 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
฿2,043
฿2,282 total
17 Sept - 18 Sept
includes taxes & fees
5.4/10 (901 reviews)
FairBridge Inn Express
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
฿3,094
฿3,457 total
14 Sept - 15 Sept
includes taxes & fees
Red Roof Inn PLUS+ South Deerfield – Amherst
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
฿3,328
฿3,718 total
30 Sept - 1 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
Quality Inn Lee - Lenox South
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
฿3,817
฿4,264 total
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA
฿4,015
฿4,484 total
15 Sept - 16 Sept
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Whitlock

The Whitlock

16 Church St Lenox MA
฿4,727
฿5,280 total
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very good! (376 reviews)
The Whitlock

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 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! 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 Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center and Pontoosuc Lake. You'll also find Swift River and Mount Greylock 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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