The Best Windsor, MA Resorts from $71

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Recommended hotels in Windsor

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

1. FairBridge Inn Express

Pittsfield

Richard

$65 nightly

Nov 19 - Nov 20

Total with taxes and fees

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

2. Rodeway Inn

Adams

Joann

$64 nightly

Nov 2 - Nov 3

Total with taxes and fees

A building entrance with a large planter with purple flowers and a small tree.

3. Hotel On North

Pittsfield

John

$132 nightly

Nov 10 - Nov 11

Total with taxes and fees

Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

Lenox

Basil

$105 nightly

Nov 1 - Nov 2

Total with taxes and fees

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.

5. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

$144 nightly

Nov 2 - Nov 3

Total with taxes and fees

A living room with a fireplace, two sofas, and four black side tables.

6. The Revival House

Adams

Katrina

$150 nightly

Nov 1 - Nov 2

Total with taxes and fees

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

7. The Central Downtown Inn & Suites

Pittsfield

Debra

$99 nightly

Oct 27 - Oct 28

Total with taxes and fees

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

$79 nightly

Oct 27 - Oct 28

Total with taxes and fees

A patio area with outdoor furniture, a fire pit, and potted plants.

9. The Springs Motel

New Ashford

Elizabeth

$106 nightly

Nov 1 - Nov 2

Total with taxes and fees

10. Berkshire Mountain Lodge

Pittsfield

Michael

$115 nightly

Nov 24 - Nov 25

Total with taxes and fees

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

Ginger

$95 nightly

Nov 24 - Nov 25

Total with taxes and fees

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

12. Berkshire Inn

Pittsfield

cheryl

$79 nightly

Nov 26 - Nov 27

Total with taxes and fees

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

13. Berkshire Village Carriage House - Super Private!!

Lanesborough

Mary R.

$189 nightly

Oct 27 - Oct 28

Total with taxes and fees

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

14. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

$119 nightly

Nov 15 - Nov 16

Total with taxes and fees

15. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

$119 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious hotel lobby with multiple seating areas, large windows, and a television.

16. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

$110 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

17. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

$98 nightly

Nov 15 - Nov 16

Total with taxes and fees

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

18. Harbour House Inn

Cheshire

Gregory

$254 nightly

Oct 28 - Oct 29

Total with taxes and fees

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

19. Vacation Village in the Berkshires

Williamstown

Luke

$128 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

20. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Allie T.

$324 nightly

Oct 29 - Oct 30

Total with taxes and fees

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Top Windsor Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every night. If you want an old school meet the other visitors experience, you could probably have it. There is laundry on every floor. I think the awesome prices we got were due to it not being ski season? once we go there and did some driving around we realized Bousquet mountain was right there. So probably a brilliant choice for a long family ski trip. There are a couple of really convenient grocery stores and restaurants right there - but most of the tourist attractions and pittsfield downtown are 10minute or so drive away. Beautiful lobby/property. Enjoyed the coffee machine in the library. Really great experience. We'd love to stay again."

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"First off, the hotel is super conveniently located. We were traveling with 2 other couples, and I booked 3 standard rooms, 2 queen beds in each. The rooms were clean, the beds were comfortable. The room we stayed in had some minor issues. As we only stayed one night, it wasn't a bother. We were going ro report the issues when we checked out, but the front desk had a note saying they would be back in just a moment please leave any keys on the counter when you checked out. We had reservations for breakfast to make so we couldn't wait around for someone to come back. Our issue with our room was just that the light on the bureau did not light up the bulbs flicker but wouldn't light. Also the toilet wasn't secured properly to the floor so when you sat down on it and then stood up the toilet tank would clunk loudly. We were on an end unit so we didn't have a neighbor to bother but I would think they would want to attend to that. The other thing that was slightly strange is the other two rooms that were identical in the booking, but ine had different amenities. One had a refrigerator but the other two rooms didn't. One was missing an iron. All minor things and it did not affect the quality of our stay. Overall it was a very good value for the money, clean, comfortable, and perfectly situated near of the places we were visiting. When we checked in the lady behind the desk was pleasant and accommodating and greeted us warmly. I would be confident booking another stay here."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"After having been away from The Black Swan Inn since the 1980’s, I was happy to see the hotel is being maintained and cared for. The lakeside views are beautiful (even though I had to pay an up charge to get this side upon check in). The room was large. My only wish regarding the bedding, is that the pillows weren’t so hard and stiff. Balconies need a little maintenance. A staff member, “Rocky”, was especially nice to be greeted by in the breakfast room on the morning we left. Thank you."

Find out more about Windsor

Windsor Resorts information

Number of reviews	11,906
Accommodation	8 Resorts
Lowest Price	$71
Highest Price	$361

Frequently asked questions

What is Windsor like for a resort vacation?

You deserve a getaway, and a resort is the perfect place to pamper yourself with the amenities and services you need for a relaxing stay in Windsor. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, blissful spa treatments, or nightly entertainment options.

What's a favorite resort for my stay in Windsor?

Our top-rated resorts near Windsor: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Windsor. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.8 mi (20.7 km) from Windsor. Access to ski-in/ski-out access, a fitness center, and an indoor pool.

What can I do in Windsor?

Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Pontoosuc Lake are a few interesting places to visit nearby. In the area, other attractions include Swift River and Mount Greylock.

What's the weather like in Windsor?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What's the best way to get to and around Windsor?

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the city center. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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Recommended hotels in Windsor

1. FairBridge Inn Express

2. Rodeway Inn

3. Hotel On North

4. The Yankee Inn

5. The Trail in Adams - Berkshires’ Art Hotel

6. The Revival House

7. The Central Downtown Inn & Suites

8. Howard Johnson by Wyndham Lenox

9. The Springs Motel

10. Berkshire Mountain Lodge

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

12. Berkshire Inn

13. Berkshire Village Carriage House - Super Private!!

14. Hilton Garden Inn Lenox Pittsfield

15. Hotel Downstreet, an Ascend Collection Hotel

16. Hampton Inn & Suites Berkshires-Lenox

17. Best Western Plus Berkshire Hills Inn & Suites

18. Harbour House Inn

19. Vacation Village in the Berkshires

20. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Red Roof Inn PLUS+ South Deerfield – Amherst

Hotel On North

Vacation Village in the Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Jiminy Peak Mountain Resort

The Cornell Inn, Lenox & The Berkshires

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

Find out more about Windsor

Windsor Resorts information

Frequently asked questions

Explore a world of travel with Expedia

Best Resorts in Windsor

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Recommended hotels in Windsor

1. FairBridge Inn Express

2. Rodeway Inn

3. Hotel On North

4. The Yankee Inn

5. The Trail in Adams - Berkshires’ Art Hotel

6. The Revival House

7. The Central Downtown Inn & Suites

8. Howard Johnson by Wyndham Lenox

9. The Springs Motel

10. Berkshire Mountain Lodge

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

12. Berkshire Inn

13. Berkshire Village Carriage House - Super Private!!

14. Hilton Garden Inn Lenox Pittsfield

15. Hotel Downstreet, an Ascend Collection Hotel

16. Hampton Inn & Suites Berkshires-Lenox

17. Best Western Plus Berkshire Hills Inn & Suites

18. Harbour House Inn

19. Vacation Village in the Berkshires

20. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Find out more about Windsor

Windsor Resorts information

Frequently asked questions

Explore a world of travel with Expedia