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Windsor hotels from HK$588

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Check prices for these dates

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30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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Our top choices for Windsor hotels

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

1. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,004 reviews)
"Great experience and Great onsite restaurant."
United States
mary ellen
The price is HK$935
HK$1,045 total
includes taxes & fees
19 Nov - 20 Nov
Hotel Downstreet, an Ascend Collection Hotel
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

2. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (971 reviews)
"Very nice hotel"
United States
Philip
The price is HK$911
HK$1,017 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

3. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,990
HK$2,104 total
includes taxes & fees
12 Nov - 13 Nov
Harbour House Inn
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

4. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (527 reviews)
"Great stay"
United States
Ram
The price is HK$1,166
HK$1,477 total
includes taxes & fees
30 Nov - 1 Dec
The Porches Inn at Mass MoCA
A living room with a fireplace, two sofas, and four black side tables.

5. The Revival House

The Revival House
3.0 star property
Adams
8.8 out of 10, Excellent, (43 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is HK$1,083
HK$1,210 total
includes taxes & fees
9 Nov - 10 Nov
The Revival House
Two Adirondack chairs facing a river with a forested hill in the background.

6. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The location was good for our trip."
United States
Basil
The price is HK$832
HK$929 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is HK$860
HK$961 total
includes taxes & fees
10 Nov - 11 Nov
Hampton Inn & Suites Berkshires-Lenox
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,810 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is HK$630
HK$790 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

9. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (158 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is HK$1,363
HK$1,523 total
includes taxes & fees
2 Nov - 3 Nov
The Trail in Adams - Berkshires’ Art Hotel
A hotel patio with outdoor seating and a fire pit.

10. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is HK$931
HK$1,040 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (252 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is HK$808
HK$903 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

12. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,247 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is HK$649
HK$900 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

13. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (930 reviews)
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
United States
Richard
The price is HK$558
HK$623 total
includes taxes & fees
9 Nov - 10 Nov
FairBridge Inn Express
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,000 reviews)
"enjoyed our stay"
United States
Mark
The price is HK$808
HK$903 total
includes taxes & fees
28 Nov - 29 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

15. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (49 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is HK$1,059
HK$1,183 total
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

16. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (931 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
The price is HK$620
HK$692 total
includes taxes & fees
10 Nov - 11 Nov
Howard Johnson by Wyndham Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

17. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!"
United States
Vandhana
The price is HK$985
HK$1,101 total
includes taxes & fees
8 Nov - 9 Nov
Courtyard by Marriott Lenox Berkshires
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

18. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,000 reviews)
"Room was spacious and clean"
United States
James
The price is HK$733
HK$819 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Plus Berkshire Hills Inn & Suites
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

19. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,056 reviews)
"A very good place to stay"
United States
Madhavi R
The price is HK$957
HK$1,069 total
includes taxes & fees
29 Nov - 30 Nov
Berkshires Untold
A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

20. Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (241 reviews)
"Up on top of the mountain, the views were great. This motel faces east so sunrises are spectacular. I enjoyed the rural location and being able to go out by the fire pits was a nice touch."
United States
William
The price is HK$1,426
HK$1,508 total
includes taxes & fees
18 Nov - 19 Nov
Blue Vista Motor Lodge
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

Hotel On North

Hotel On North

10/10 Excellent
"What a nice place to stay!"
Jason 1-night trip
Posted 1 hour ago
Hotel On North

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is HK$558 per night from 9 Nov to 10 Nov
HK$558
HK$623 total
9 Nov - 10 Nov
includes taxes & fees
5.4/10 (930 reviews)

Hotels in Windsor with star-rating

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 The Yankee Inn. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Windsor is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. See all 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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