Best Windsor Hotels in 2026 from HK$544 - Fully Refundable Options

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Cottage

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Our top choices for Windsor hotels

Desk, laptop workspace, blackout curtains, iron/ironing board

1. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Glenda

HK$775

HK$865 total

includes taxes & fees

21 Sept - 22 Sept

In-room safe, desk, free WiFi, bed sheets

2. Blue Vista Motor Lodge

North Adams

Frederic

HK$1,679

HK$1,774 total

includes taxes & fees

16 Sept - 17 Sept

Desk, laptop workspace, iron/ironing board, free WiFi

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

42-inch flat-screen TV with cable channels, TV

3. The Yankee Inn

Lenox

Robert

HK$910

HK$1,016 total

includes taxes & fees

22 Sept - 23 Sept

Premium bedding, minibar, in-room safe, desk

4. Hotel On North

Pittsfield

Drew

HK$1,053

HK$1,176 total

includes taxes & fees

16 Sept - 17 Sept

Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

5. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Alexandra

HK$1,135

HK$1,268 total

includes taxes & fees

21 Sept - 22 Sept

55-inch LCD TV with digital channels, printers

Desk, iron/ironing board (on request), free WiFi

6. The Revival House

Adams

Katrina

HK$1,299

HK$1,451 total

includes taxes & fees

16 Sept - 17 Sept

7. Harbour House Inn

Cheshire

Gregory

HK$1,990

HK$2,103 total

includes taxes & fees

17 Sept - 18 Sept

In-room safe, desk, laptop workspace, blackout curtains

8. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

HK$868

HK$970 total

includes taxes & fees

1 Oct - 2 Oct

9. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

HK$1,147

HK$1,282 total

includes taxes & fees

20 Sept - 21 Sept

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

Pittsfield

Steve

HK$996

HK$1,113 total

includes taxes & fees

20 Sept - 21 Sept

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

HK$902

HK$1,007 total

includes taxes & fees

13 Oct - 14 Oct

12. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

HK$1,537

HK$1,717 total

includes taxes & fees

20 Sept - 21 Sept

Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

HK$1,042

HK$1,164 total

includes taxes & fees

23 Sept - 24 Sept

In-room safe, desk, laptop workspace, iron/ironing board

14. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

HK$620

HK$692 total

includes taxes & fees

20 Sept - 21 Sept

Desk, iron/ironing board, cots/infant beds, rollaway beds

15. Quality Inn Lee - Lenox South

Lee

Christine

HK$840

HK$938 total

includes taxes & fees

28 Sept - 29 Sept

Desk, iron/ironing board, free WiFi, bed sheets

16. FairBridge Inn Express

Pittsfield

Horace

HK$487

HK$544 total

includes taxes & fees

20 Sept - 21 Sept

28-inch TV with digital channels, Netflix, books

1 bedroom, premium bedding, desk, free WiFi

17. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

HK$1,461

HK$1,632 total

includes taxes & fees

16 Sept - 17 Sept

Blackout curtains, iron/ironing board (on request), free WiFi

18. Cozy Corner Motel

Williamstown

Janis

HK$692

HK$813 total

includes taxes & fees

23 Sept - 24 Sept

Indoor pool, outdoor pool, pool umbrellas

19. Vacation Village in the Berkshires

Williamstown

Sarah

HK$746

HK$919 total

includes taxes & fees

17 Sept - 18 Sept

20. Willows Motel Williamstown

Williamstown

Bill

HK$812

HK$907 total

includes taxes & fees

16 Sept - 17 Sept

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Top Windsor Hotel Reviews

The Yankee Inn

10/10 Excellent

"We were here for a good night’s rest on a cross country roadtrip. This place had very good Expedia reviews and I agree. Very clean, decent breakfast, plenty of hot water, a toilet that flushed properly. Did not use amenities. Sleep, shower, quiet time to read some, eat and on down the highway. Would gladly stay here again the next time thru the Berkshires."

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

10/10 Excellent

"Pristine and new. Staff was friendly and the breakfast was delicious."

Hotel On North

10/10 Excellent

"Great location, clean room!"

The Whitlock

10/10 Excellent

"Front desk staff amazing. Very quaint and well maintained building. Room large and free standing tub wonderful. Great location. Good bargin as well."

The Red Lion Inn

8/10 Good

"We stopped at the red lion Inn on our travels back home from Maine. Our room was a block away from the main building and in an old house. It was very clean and comfortable. The location in town is nice."

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent

"The staff was very helpful"

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Clean room, great location. Perfect base for a weekend in the Berkshires."

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

HK$487

HK$544 total

20 Sept - 21 Sept

includes taxes & fees

5.4/10 (905 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

HK$775

HK$865 total

21 Sept - 22 Sept

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

HK$840

HK$938 total

28 Sept - 29 Sept

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

HK$910

HK$1,016 total

22 Sept - 23 Sept

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

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

1055 South Street Pittsfield MA

HK$996

HK$1,113 total

20 Sept - 21 Sept

includes taxes & fees

9.2/10 Wonderful! (207 reviews)

The Whitlock

16 Church St Lenox MA

HK$1,127

HK$1,258 total

16 Sept - 17 Sept

includes taxes & fees

8.4/10 Very good! (383 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.

Windsor hotels from HK$544

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

1. Red Roof Inn PLUS+ South Deerfield – Amherst

2. Blue Vista Motor Lodge

3. The Yankee Inn

4. Hotel On North

5. Hotel Downstreet, an Ascend Collection Hotel

6. The Revival House

7. Harbour House Inn

8. Best Western Plus Berkshire Hills Inn & Suites

9. Hilton Garden Inn Lenox Pittsfield

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

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

12. Courtyard by Marriott Lenox Berkshires

13. Hampton Inn & Suites Berkshires-Lenox

14. Howard Johnson by Wyndham Lenox

15. Quality Inn Lee - Lenox South

16. FairBridge Inn Express

17. The Trail in Adams - Berkshires’ Art Hotel

18. Cozy Corner Motel

19. Vacation Village in the Berkshires

20. Willows Motel Williamstown

Top Windsor Hotel Reviews

The Yankee Inn

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

Hotel On North

The Whitlock

The Red Lion Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Windsor

FairBridge Inn Express

Red Roof Inn PLUS+ South Deerfield – Amherst

Quality Inn Lee - Lenox South

The Yankee Inn

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

The Whitlock

Hotels in Windsor with star-rating

Frequently asked questions

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