Top 10 Hotels in Windsor, MA from ￥13,025 - Fully Refundable Options

Compare 982 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

"The staff are absolutely wonderful. The inn is beautiful and so well cared for. And bonus the lake views are gorgeous!"

￥29,202 total

includes taxes & fees

Sep 25 - Sep 26

"The inn has an excellent location and amenities."

"Great property! Very large clean room in a unique hotel! "

￥26,235 total

includes taxes & fees

Sep 28 - Sep 29

"Great hotel, staff and restaurant!"

￥39,126 total

includes taxes & fees

Oct 5 - Oct 6

"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "

￥34,552 total

includes taxes & fees

Sep 29 - Sep 30

"Well-run and elegant property. "

￥66,304 total

includes taxes & fees

Sep 25 - Sep 26

"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "

￥20,883 total

includes taxes & fees

Sep 28 - Sep 29

Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

"Inn was gorgeous and staff exceptional!"

"Excellent place. Bountiful view. "

￥22,918 total

includes taxes & fees

Sep 28 - Sep 29

Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "

￥100,005 total

includes taxes & fees

Oct 8 - Oct 9

Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down comforters

"Great hotel, lovely pool and hot tub. We got upgraded to a suite!"

￥34,311 total

includes taxes & fees

Sep 28 - Sep 29

"Lovely Inn and very responsive and approachable staff. "

￥22,072 total

includes taxes & fees

Oct 5 - Oct 6

"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "

￥37,267 total

includes taxes & fees

Sep 25 - Sep 26

"Very casual and easy check in and out; lovely and substantial breakfast"

￥30,119 total

includes taxes & fees

Oct 1 - Oct 2

"Great breakfast, friendly helpful staff, pretty yard, good location "

￥55,261 total

includes taxes & fees

Oct 8 - Oct 9

"It was clean and in a convenient location "

￥19,033 total

includes taxes & fees

Oct 2 - Oct 3

"We always stay at the Garden Inn when visiting the Berkshires."

￥26,446 total

includes taxes & fees

Sep 28 - Sep 29

"ease of late check in. Super comfortable room."

"Fabulous place"

￥26,545 total

includes taxes & fees

Sep 29 - Sep 30

"It was a great Stay where we had to it was a good area I would come back to this place again "

￥18,677 total

includes taxes & fees

Sep 28 - Sep 29

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Always very relaxing. Kids love the pool and we enjoy the hot tub and views"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

" To whom it may concern, My wife & I were blessed beyond measures with Chris the recepcionista who was an amazing incredible human being who treated us like family. We needed some direction to southbridge Ma. He explain to us the best way to get there and back to the hotel. Also the other gentleman working along side of him also assisted us as well. Thank you for this beautiful experience and to let you know that we will come again. Please give our love to the precious lady housekeeper who blessed us as well. "

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA

￥11,661

￥13,025 total

Sep 28 - Sep 29

includes taxes & fees

7.4/10 Good! (802 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 traveler data. Other good options for your visit to the area are Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental in Windsor?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This vacation home rental outside of Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

Where can I learn more about changing or cancelling my trip to Windsor?

For more information about updating your trip to Windsor or cancelling it, click here.

What's the best hotel for staying near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations 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. Check out what more to see and do in Expedia's Windsor guide.

What's the seasonal 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.

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Compare 982 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lakehouse Inn

Lakehouse Inn

Devonfield Inn B&B

Devonfield Inn B&B

Hotel On North

Hotel On North

The Williams Inn

The Williams Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm

The Inn at Stockbridge

The Inn at Stockbridge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Brook Farm Inn

Brook Farm Inn

Maple Terrace Motel

Maple Terrace Motel

33 Main

33 Main

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

Blooming Inn

Blooming Inn

Harbour House Inn

Harbour House Inn

Shaker Mill Inn

Shaker Mill Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Williamstown Motel

Williamstown Motel

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Chambery Inn

Chambery Inn

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

More cheap stays in Windsor

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Frequently asked questions

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