Find hotels in Windsor, MA from ￥11,931

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Dec 11 - Dec 12
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Dec 12 - Dec 13
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Our top choices for Windsor hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodations include refrigerators and microwaves. Unwind in the hot tub, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.
"Great stay there!! Very friendly staff"
United States
Ann
The price is ￥11,730
￥13,103 total
includes taxes & fees
Dec 24 - Dec 25
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Center. After working out in the 24-hour fitness center, savor Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,761
￥17,605 total
includes taxes & fees
Dec 21 - Dec 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2170)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥16,193
￥19,796 total
includes taxes & fees
Dec 17 - Dec 18
Vacation Village in the Berkshires
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (813)
This Lenox lodge combines comfort with convenience, just a short drive from Tanglewood Music Center. The Club Room serves delicious American cuisine, while a welcoming bar and outdoor terrace enhance your stay. Kennedy Park and Pleasant Valley Wilderness Sanctuary await nearby.
"Easiest check in and out. Great food in dining room. "
United States
William
The price is ￥17,077
￥19,076 total
includes taxes & fees
Dec 16 - Dec 17
Berkshires Untold
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (984)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transportation Center, this hotel offers peaceful accommodations with an indoor pool. Enjoy the fitness center, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theater.
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,437
￥16,127 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (798)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Center and Berkshire Theatre Festival.
"Place was great!"
United States
Benjamin
The price is ￥18,782
￥24,024 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
Located 10 minutes from Tanglewood Music Center, this hotel provides complimentary breakfast, WiFi, and parking. After exploring nearby attractions, unwind in the indoor pool or soothing hot tub for a peaceful end to your Pittsfield adventure.
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥16,867
￥18,840 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥23,443
￥33,192 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Red Lion Inn
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
Charming Cornell Inn offers a peaceful garden retreat within walking distance to Lenox attractions. Enjoy complimentary gourmet breakfast and unwind with a drink at the bar before retiring to comfortable rooms. Free WiFi and parking enhance your Berkshires getaway.
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ￥26,023
￥29,938 total
includes taxes & fees
Dec 14 - Dec 15
The Cornell Inn, Lenox & The Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ￥16,795
￥18,759 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (787)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is ￥15,369
￥20,646 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Berkshire Mountain Lodge
Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1003)
Discover convenience at this South Deerfield hotel, just minutes from Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy complimentary WiFi and parking, spotless rooms, and attentive 24-hour service, all within 15 minutes of UMass Amherst.
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is ￥13,875
￥15,497 total
includes taxes & fees
Dec 14 - Dec 15
Red Roof Inn PLUS+ South Deerfield – Amherst
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness center or enjoy nearby skiing options. Tanglewood Music Center and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ￥14,685
￥16,403 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property - evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
Minutes from Barrington Stage Company and Berkshire Athenaeum, this hotel offers comfortable rooms and attentive service. Just a 2-minute walk from Pittsfield Intermodal Transportation Center, enjoy room service and the convenient downtown location.
"Clean room and staff was super friendly"
United States
Yuen
The price is ￥23,205
￥25,921 total
includes taxes & fees
Dec 12 - Dec 13
Hotel On North
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down comforters, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"It is the perfect place to stay!"
United States
Darrell
The price is ￥22,527
￥28,667 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Porches Inn at Mass MoCA
Front of property - evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (549)
Nestled near Williams College, this inviting hotel offers free WiFi and parking plus a fitness center. Savor American cuisine at The Barn Kitchen & Bar, unwind on the terrace, or explore nearby Denison Park. Helpful staff enhance your stay.
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is ￥29,468
￥32,916 total
includes taxes & fees
Dec 21 - Dec 22
The Williams Inn
Exterior
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
Immerse in the tranquility of Williamstown at this cozy retreat with free continental breakfast and WiFi. Located near Mountain Meadow Preserve and Williamstown Trailhead, this motel offers clean rooms and exceptionally helpful staff.
"It's very good for stay over"
United States
Frances
The price is ￥10,746
￥12,003 total
includes taxes & fees
Dec 14 - Dec 15
The Villager Motel
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
Experience tranquility at this peaceful B&B in Lee, where deep-tissue massages and aromatherapy await. Just a 10-minute drive from Tanglewood Music Center, guests enjoy access to a hot tub, terrace, and snack bar while exploring nearby Berkshire attractions.
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
Guests love the attentive service and complimentary breakfast at this welcoming hotel. Located near Colonial Plaza, it offers an indoor pool for year-round enjoyment, 24-hour fitness center, and convenient amenities including free WiFi and parking.
"our stay was great."
United States
nathaniel
The price is ￥24,451
￥27,311 total
includes taxes & fees
Dec 15 - Dec 16
Fairfield Inn & Suites by Marriott Williamstown
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (590)
Set in Lenox with easy access to local attractions, this hotel offers an indoor pool and fitness center. Grab a bite at the café or unwind at the bar after exploring Kennedy Park. Rooms include refrigerators and microwaves for added convenience.
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥21,025
￥23,485 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Lenox Berkshires
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "
Meaghan 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

More cheap stays in Windsor

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is ￥11,730 per night from Dec 24 to Dec 25
￥11,730
￥13,103 total
Dec 24 - Dec 25
includes taxes & fees
9/10 Wonderful! (1,000 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 Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Windsor.
What's the top vacation rental in Windsor?
Peace and quiet on the lake: This vacation home rental outside of Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. 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 Wahconah Falls State Park, Crane Museum of Papermaking, and Mount Greylock State Reservation Visitor Center. You'll also find Skyline Trail and Swift River 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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