Top 10 Hotels in Windsor, MA (from $77) 2026 - Competitive Prices

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Windsor

Pet friendly

Hot tub

Condo

Apartment

Pool

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Windsor hotels

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

A spacious living room with large windows, a fireplace, and a variety of seating options.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

1. Vacation Village in the Berkshires

Williamstown

Rosario

$122 nightly

$136 total

Sep 27 - Sep 28

Total with taxes and fees

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

2. Berkshire Mountain Lodge

Pittsfield

Jonathan

$109 nightly

$121 total

Oct 1 - Oct 2

Total with taxes and fees

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.

3. D. Hotel Suites & Spa

Holyoke

Margaret

$142 nightly

$158 total

Sep 27 - Sep 28

Total with taxes and fees

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A cozy library with bookshelves, a fireplace, and comfortable seating.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

4. Berkshires Untold

Lenox

Olyvia

$143 nightly

$160 total

Sep 28 - Sep 29

Total with taxes and fees

A building with a porch and multiple windows, surrounded by purple flowers.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A café with a display case, a frozen food section, and a marketplace sign.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Jared

$135 nightly

$150 total

Sep 28 - Sep 29

Total with taxes and fees

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A bar with wooden floors and shelves filled with bottles.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

6. The Red Lion Inn

Stockbridge

Gerald

$198 nightly

$221 total

Sep 29 - Sep 30

Total with taxes and fees

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

7. The Yankee Inn

Lenox

William

$109 nightly

$122 total

Oct 25 - Oct 26

Total with taxes and fees

A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

A hotel room with two beds, a TV, a desk, and a chair.

A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.

A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.

8. Hotel Northampton

Northampton

Beth

$140 nightly

$157 total

Sep 27 - Sep 28

Total with taxes and fees

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

A modern hotel room with a dining area, a sofa, a bed, and a TV.

A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.

A modern hotel room with a bed, sofa, dining table, and chairs.

9. The Ellery

Northampton

Jay

$138 nightly

$154 total

Oct 26 - Oct 27

Total with taxes and fees

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A bar area with wooden beams, red chairs, and a long wooden table.

10. The Williams Inn

Williamstown

Adam

$183 nightly

$204 total

Sep 27 - Sep 28

Total with taxes and fees

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

11. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Howard

$138 nightly

$154 total

Sep 28 - Sep 29

Total with taxes and fees

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

A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.

A gazebo in a garden with a house in the background.

A gazebo in a lush garden with flowering plants and a large tree.

12. Harbour House Inn

Cheshire

Virginia

$254 nightly

$268 total

Sep 28 - Sep 29

Total with taxes and fees

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

A modern cafe with a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A snack bar with shelves of snacks and a refrigerated display.

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

Pittsfield

Wendy

$122 nightly

$136 total

Oct 19 - Oct 20

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.

A hallway with a wooden door, a bench, and a staircase.

A garden with a wooden house, a tree, and a person tending to plants.

A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

14. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

$181 nightly

$202 total

Sep 28 - Sep 29

Total with taxes and fees

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

15. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

$212 nightly

$236 total

Sep 28 - Sep 29

Total with taxes and fees

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

A library with bookshelves, a television, and two armchairs.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

16. Hotel On North

Pittsfield

Donna

$152 nightly

$170 total

Oct 5 - Oct 6

Total with taxes and fees

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern interior with a large window, a wooden table, and bar stools.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

17. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Karl

$135 nightly

$151 total

Oct 14 - Oct 15

Total with taxes and fees

A resort with multiple buildings, a parking area, and a mountainous backdrop.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

18. Jiminy Peak Mountain Resort

Hancock

Karen

$149 nightly

$166 total

Oct 18 - Oct 19

Total with taxes and fees

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

A hotel room with a desk, computer, TV, and a chair.

A dining area with wooden tables and chairs, a television, and a door with a sign.

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

19. FairBridge Inn Express

Pittsfield

ERICIA

$69 nightly

$77 total

Sep 27 - Sep 28

Total with taxes and fees

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

A wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.

A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.

20. Vikings Villages Resort

Guilford

Alisha

$200 nightly

$219 total

Oct 25 - Oct 26

Total with taxes and fees

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Where to stay near Windsor

Windsor, a lovely place in western MA, offers a perfect blend of outdoor adventure and scenic beauty. For your next trip, explore family-friendly activities and romantic spots nearby, making it a convenient location to enjoy nature and create lasting memories.

A church with a green spire and a red brick building with arched windows.

A historic building with a clock, a flag, and a street lamp.

A church with a tall steeple and a green roof.

A lakeside house with a dock and a covered area, a sunset over the water, and mountains in the background.

A cityscape with a rainbow, red buildings, and a church.

Pittsfield

Discover Pittsfield, a vibrant destination perfectly suited for travelers seeking a blend of culture and outdoor adventure. With a rich tapestry of experiences, visitors can explore the historic Hancock Shaker Village, the enlightening Berkshire Museum, and the serene National Shrine of the Divine Mercy. Whether indulging in skiing during the winter or enjoying the nearby lake and mountain in warmer months, Pittsfield offers year-round excitement. Located about 11 miles by car from Windsor, it's a smart choice for your next hotel booking.

See properties

A white building with a sign reading "Hancock Town Hall 1850" in front of a forested hillside.

Two large wooden silos, a yellow building with a tower, and a fenced area with a stone wall.

A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

A rural landscape with sheep grazing, two wooden silos, and a forested hill in the background.

A rural landscape with a fenced field, several sheep grazing, and two wooden barns in the background.

Hancock

Experience the charm of Hancock, an excellent hub for families and nature enthusiasts eager to explore stunning outdoor activities. With nearby attractions like the historic Williams College, the breathtaking Mount Greylock, and the serene Mount Greylock State Reservation, visitors can immerse themselves in both adventure and tranquility. Hancock is also just 12 miles from Windsor, making it a smart choice for a memorable getaway. Enjoy a refreshing stay that combines relaxation with exciting experiences.

See properties

A railway tunnel with a curved ceiling and tracks.

A building with 'MASS MoCA' written on it, surrounded by greenery and hills.

A winding road through a forested area with autumn-colored trees and a rocky cliff.

A street lined with multi-story buildings, including a red brick building and a white building with blue trim. There are storefronts with signs, a fire hydrant, and a street lamp.

A mountainous landscape with a prominent rock formation in the foreground and a valley with scattered buildings in the distance under a sunset sky.

North Adams

If you are a traveler seeking adventure and culture, look no further than North Adams, known for its vibrant arts scene and beautiful outdoor experiences. Explore the Massachusetts Museum of Contemporary Art, enjoy the historic charm of Williams College, and appreciate the stunning collections at The Clark Art Institute. Located about 14 miles by car from Windsor, North Adams offers a unique blend of activities year-round, making it a smart choice for your next getaway.

See properties

Savoy

Savoy stands out as a prime spot for travelers interested in family-oriented adventures and stunning natural scenery. With attractions like the Massachusetts Museum of Contemporary Art, the breathtaking Mount Greylock, and historic Williams College, Savoy offers a rich blend of culture and outdoor activities. Just about 4 miles from Windsor, it provides easy access to weekend getaways and outdoor fun year-round. Choosing Savoy for your stay ensures a memorable escape into nature’s beauty and local charm.

See properties

Peru

Travelers seeking a weekend getaway or a family adventure will find Peru, Massachusetts, to be the ideal base for their vacation, featuring stunning natural landscapes and a wealth of outdoor activities. Visitors can explore the breathtaking Wahconah Falls State Park, visit the serene National Shrine of the Divine Mercy, or dive into local history at the Crane Museum of Papermaking. Located about 5 miles from Windsor, Peru offers easy access to its attractions, making it a smart choice for your next stay.

See properties

Stay near popular attractions around Windsor

Windsor is a paradise for outdoor enthusiasts, offering breathtaking scenery and countless adventure opportunities. Explore nature reserves and mountains that promise unforgettable experiences. Don't forget to grab a Windsor map to help navigate your journey through this beautiful landscape!

A waterfall cascading over rocks in a forested area.

Wahconah Falls State Park

A go-to area recognized for its stunning scenery, Wahconah Falls State Park offers outdoor enthusiasts a chance to explore beautiful landscapes and enjoy adventurous activities. Located about 4 miles from Windsor, it provides easy access to nature's tranquility, making it an ideal spot for a refreshing getaway.

See properties

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)

Often cited as a favorite among art lovers, the Massachusetts Museum of Contemporary Art in North Adams offers a unique blend of innovative exhibitions and cultural vibes. Located about 14 miles by car from Windsor, it’s an easy trip for a memorable day out, making it a convenient stop for travelers.

See properties

A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.

Mount Greylock

9.4/10 (180 reviews)

Highly recommended for outdoor enthusiasts, Mount Greylock offers breathtaking scenery and adventure in the heart of Massachusetts. With its stunning vistas and diverse trails, it's a perfect spot for exploring nature. Located about 11 miles from Windsor, it's an easy trip to enjoy a day of outdoor fun.

See properties

A town with historic buildings, a prominent yellow church, and a mountainous backdrop.

Berkshire Museum

8.4/10 (26 reviews)

Perfectly suited for families, Berkshire Museum in Pittsfield offers a delightful blend of natural history and cultural experiences. Located about 11 miles by car from Windsor, this museum provides engaging exhibits that captivate visitors of all ages. Staying nearby makes it easy to explore this enriching destination.

See properties

Crane Museum of Papermaking

No trip is complete without a visit to the Crane Museum of Papermaking, a delightful destination for history buffs and art lovers alike. This museum showcases the fascinating culture of papermaking through engaging exhibits. Located about 7 miles from Windsor, it's an easy stop that enriches your exploration of the area.

See properties

Tannery Falls

An essential stop for outdoor adventurers, Tannery Falls offers a stunning display of nature's beauty in Savoy, Massachusetts. Known for its romantic ambiance and breathtaking waterfall, this destination is about 8 miles from Windsor, making it a convenient spot for a refreshing escape into the wilderness.

See properties

St Mary's of the Assumption Church

10.0/10 (1 review)

A fascinating mix of history and culture awaits visitors to St Mary's of the Assumption Church, located about 7 miles from Windsor. This charming church offers a serene atmosphere and beautiful architecture, making it a perfect stop for those seeking a reflective experience. Staying nearby allows easy access to this serene landmark.

See properties

Zoar Outdoor/Deerfield Valley Canopy Tours

10.0/10 (1 review)

A must-see for adventure seekers, Zoar Outdoor/Deerfield Valley Canopy Tours offers an exhilarating experience with its thrilling zip lines set amid stunning landscapes. Located about 12 miles from Windsor, it provides easy access for those looking to immerse themselves in outdoor fun and excitement.

See properties

Top Windsor Hotel Reviews

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

10/10 Excellent

"Great location to Tanglewood, 11 min ride. Clean room, comfy beds, great shower. Loved the pool and hot tub. Breakfast was just okay. We went down 20 minutes before breakfast was to be closed and not much there to be had. I had to ask for a bagel and no waffles."

Vacation Village in the Berkshires

10/10 Excellent

"great for families"

The Yankee Inn

10/10 Excellent

"No Pool or hot tub available"

Berkshire Mountain Lodge

8/10 Good

"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The facilities and property made for a wonderful family visit to the Bershires."

Quality Inn Lee - Lenox South

8/10 Good

"Great location for our trip into NE."

Berkshires Untold

8/10 Good

"Liked he cleanliness. Room was very cold and no heat was available."

Jiminy Peak Mountain Resort

10/10 Excellent

"Even in the off season it was beautiful."

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

$69 nightly

$77 total

Sep 27 - Sep 28

Total with taxes and fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

$79 nightly

$88 total

Sep 27 - Sep 28

Total with taxes and fees

7.6/10 Good! (917 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

$99 nightly

$110 total

Sep 29 - Sep 30

Total with taxes and fees

7.2/10 Good! (1,003 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

$109 nightly

$122 total

Oct 25 - Oct 26

Total with taxes and fees

9.2/10 Wonderful! (1,009 reviews)

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

1055 South Street Pittsfield MA

$122 nightly

$136 total

Oct 19 - Oct 20

Total with taxes and fees

9.4/10 Exceptional! (218 reviews)

The Whitlock

16 Church St Lenox MA

$139 nightly

$155 total

Sep 27 - Sep 28

Total with taxes and fees

Hotels in Windsor with star-rating

Find out more about Windsor

Top reasons to visit Windsor

Outdoor Adventures: Windsor is a paradise for outdoor enthusiasts, offering skiing, hiking, and breathtaking scenery in nature reserves and mountains.
Windsor Wine Country: Savor delightful wine tastings in the picturesque Windsor Wine Country, perfect for a relaxing day.
Charming Accommodations: Enjoy a variety of lodging options, from cozy bed & breakfasts to relaxing resorts, catering to all travelers.
Family-Friendly Activities: Windsor offers family-friendly attractions and picnic spots, making it ideal for vacations with loved ones.
Vibrant Local Culture: Explore nearby downtown Healdsburg for a romantic atmosphere and diverse dining experiences.

Find great hotels near Windsor

Explore a range of delightful hotel accommodations in Windsor, Massachusetts, perfect for families, couples, and adventure seekers alike. Whether you're looking for a cozy bed & breakfast or a relaxing resort, Windsor offers various lodging options to suit your needs. Enjoy a memorable vacation experience with well-appointed suites and convenient access to local attractions. Start planning your getaway in this charming town today.

Berkshire Mountain Lodge: Berkshire Mountain Lodge is a charming 3-star lodge with a guest rating of 9.0, ideal for those seeking an adventurous vacation in the picturesque Berkshires. Located 13 miles from Windsor, this lodge is perfect for ski enthusiasts and golfers alike. With access to ski shuttles and lifts nearby, guests can enjoy exhilarating winter sports. For the summer adventurers, activities like kayaking, ziplining, and biking rentals are available nearby. The lodge also features on-site golf experiences, making it a versatile choice for those looking to immerse themselves in outdoor recreation year-round.
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Holiday Inn & Suites Pittsfield-Berkshires by IHG is a welcoming 3-star hotel rated at 8.0, situated 11 miles from Windsor. This family-friendly hotel caters to adventurous spirits, offering a range of activities such as cross-country skiing, fishing, and horse riding in the nearby area. With amenities tailored for children, including free cribs and breakfast options, it ensures a comfortable stay for families. The property is conveniently located near a winery vineyard, making it an excellent choice for those looking to explore local flavors while enjoying a blend of relaxation and adventure.
Club Wyndham Bentley Brook: Club Wyndham Bentley Brook is a highly-rated 3-star hotel with a guest rating of 9.2, located 13 miles from Windsor. This property is a haven for ski lovers and adventure seekers, providing easy access to ski shuttles and lifts. Guests can enjoy on-site snowboarding and nearby cross-country skiing, as well as hiking opportunities. The inviting accommodations and excellent amenities make it a perfect retreat for those looking to indulge in winter sports while experiencing the breathtaking beauty of the Berkshires.

Where to stay near Windsor

Windsor, Massachusetts offers a perfect blend of outdoor adventure and scenic beauty, ideal for family-friendly vacations. Explore the charming local attractions, including the picturesque Windsor Wine Country, where you can indulge in delightful tastings. Nearby, the vibrant atmosphere of downtown Healdsburg invites you to enjoy its romantic ambiance and diverse dining options. Whether you're seeking an adventurous outing or a relaxing retreat, Windsor and its surroundings promise unforgettable experiences.

Pittsfield: Located 11 miles from Windsor, Pittsfield is a vibrant city that offers an exciting mix of outdoor adventures and urban charm. Known for its skiing opportunities, visitors flock here during the peak months of June to August for thrilling sports experiences. With nearby ski resorts and fields, winter sports enthusiasts will find plenty to enjoy. The city's landscape is adorned with beautiful lakes and mountains, making it a picturesque destination year-round. Don't miss the local waterpark for family-friendly fun during the warmer months.
Hancock: Just 12 miles from Windsor, Hancock is another great destination for outdoor lovers. The city sees increased visitor numbers from March to April and again in July, thanks to its excellent skiing facilities. Hancock is surrounded by stunning mountains and serene lakes, perfect for both adrenaline-seeking adventurers and those looking to unwind in nature. The urban parks here provide ample space for relaxation and picnics, making it a well-rounded spot for visitors seeking both adventure and tranquility.
North Adams: Situated 14 miles away from Windsor, North Adams blends culture and outdoor activities seamlessly. With peak travel seasons in June to July and September, this city attracts those interested in adventurous pursuits and cultural experiences. Visitors can enjoy live music concerts and explore the local art museum and cultural center, adding a unique flair to their experience. The public art scattered throughout the city enhances its artistic vibe, making it a wonderful place to wander and soak in the creative atmosphere.

Things to do in Windsor

Windsor, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can enjoy skiing at nearby resorts and explore various ski fields. For a more relaxed experience, there are beautiful picnic spots where you can soak in the natural beauty of the area. Whether you're hitting the slopes or enjoying a leisurely day outdoors, Windsor offers a delightful escape for nature lovers and adventure seekers alike.

Shopping

In Windsor, you’ll find quaint shops offering unique gifts and local souvenirs. If you're up for a drive, head to the Lee Premium Outlets for brand-name bargains or explore the shops in nearby Great Barrington for a charming shopping experience.

Recreation

Experience tranquility at Kripalu Center for Yoga & Health, offering yoga classes and wellness workshops surrounded by nature. Explore the scenic hiking trails of the Berkshires for refreshing outdoor activities, or unwind with a soothing massage at a local spa to rejuvenate your mind and body.

Adventure

Explore Windsor State Forest for hiking and mountain biking amid picturesque landscapes and diverse wildlife. Try fishing or kayaking at nearby lakes for a refreshing outdoor experience. Don't miss the scenic views from the top of Mount Greylock, the highest peak in Massachusetts, offering thrilling adventures and stunning vistas.

Nightlife

In Windsor, Massachusetts, the nightlife is cozy and relaxed, featuring local pubs like The Windsor Tavern, where you can enjoy craft beers and live music. Nearby, outdoor events and seasonal festivals add to the vibrant atmosphere, making for a welcoming evening experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windsor

The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windsor are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Saturday.
Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your preferences, such as your budget, desired location, and type of hotel you’re looking for. To find the best prices and deals, simply arrange the price filter from lowest to highest.
Consider bundling your trip: You can save money by booking an Expedia package that combines your Windsor hotel stay with your flights and activities.

Find the best attractions near Windsor

Windsor, Massachusetts, is a haven for outdoor enthusiasts, offering stunning scenery and adventure opportunities. Explore its nature reserves and mountains, perfect for hiking and enjoying the great outdoors. Whether you're seeking thrilling adventures or a taste of local culture, Windsor's attractions promise memorable experiences for every traveler. Embrace the beauty and excitement of this charming destination.

Massachusetts Museum of Contemporary Art: Experience the vibrant world of modern art at this expansive cultural center, showcasing innovative exhibitions and installations. The museum's unique architecture and engaging programming make it a must-visit for art enthusiasts.
Mount Greylock: Embrace adventure at Massachusetts' highest peak, where breathtaking scenery awaits. Enjoy hiking trails, stunning views, and the thrill of outdoor activities, making it a perfect spot for nature lovers and thrill-seekers alike.
Berkshire Museum: Discover a blend of art, history, and science at this family-friendly museum. With interactive exhibits and engaging programs, the Berkshire Museum offers a fun and educational experience for visitors of all ages.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	19.9°F (-6.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	22.1°F (-5.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Average
March	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	41.4°F (5.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	53.8°F (12.1°C)	Light Rain	Mostly Sunny	Average	Average
June	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Average	Average
July	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly High
September	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Average	Average
October	47.7°F (8.7°C)	Light Rain	Mostly Cloudy	Moderately High	Slightly High
November	35.4°F (1.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
December	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

The nearest major airports for your trip to Windsor

When visiting Windsor, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is 44 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the Marriott Hartford Downtown, 12 miles away. ALBany, NY (ALB-Albany Intl.), located 42 miles from Windsor, offers accommodations such as The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. For those considering Manchester, NH (MHT-Manchester-Boston Regional), it's 87 miles away, featuring hotels like The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both just 4 miles from the airport.

Frequently asked questions

What is the best area to stay in Windsor?

The best area to stay in Windsor, Massachusetts, is near the town center, particularly along Route 9, for convenient access to local attractions and the Berkshire Mountains.Windsor itself is a small, quiet town known for its natural beauty and outdoor activities. Staying near the town center provides easy access to the Windsor Historical Society and the local general store. This area is ideal for travelers seeking a peaceful retreat and proximity to hiking trails and scenic drives.For couples looking for a tranquil getaway with access to nature, staying in a guesthouse or inn located in the hills surrounding the town center is an excellent choice. These accommodations often offer picturesque views and a chance to relax away from any hustle, while still being a short drive from attractions like the Windsor State Forest.

When is the best time to go to Windsor?

The best time to visit Windsor is during the summer months, from June to August, when the weather is warm and conducive to outdoor activities, or in the fall, from September to October, for stunning foliage.Summer in Windsor offers pleasant temperatures, typically ranging from the mid-60s to high 70s Fahrenheit, making it ideal for exploring the natural beauty of the Berkshires. This season is great for hiking trails, enjoying the numerous lakes and ponds, and participating in local outdoor events. The longer daylight hours also allow for more extensive sightseeing.For those who appreciate natural beauty, early to mid-fall is a spectacular time to visit. The Berkshire region is renowned for its vibrant autumn colors, with the hillsides transforming into a canvas of reds, oranges, and yellows.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor.

How much is the nightly rate at a Windsor hotel?

Prices for hotels in Windsor often vary, but you can find a great deal from $77 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia

Things to do in Western Massachusetts

Find hotels in Windsor, MA from $77

Upfront pricing

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. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. D. Hotel Suites & Spa

4. Berkshires Untold

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

6. The Red Lion Inn

7. The Yankee Inn

8. Hotel Northampton

9. The Ellery

10. The Williams Inn

11. The Black Swan Lee - Lenox, an Ascend Collection Hotel

12. Harbour House Inn

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

14. The Trail in Adams - Berkshires’ Art Hotel

15. The Cornell Inn, Lenox & The Berkshires

16. Hotel On North

17. Hotel Downstreet, an Ascend Collection Hotel

18. Jiminy Peak Mountain Resort

19. FairBridge Inn Express

20. Vikings Villages Resort

Where to stay near Windsor

Pittsfield

Hancock

North Adams

Savoy

Peru

Stay near popular attractions around Windsor

Wahconah Falls State Park

Massachusetts Museum of Contemporary Art

Mount Greylock

Berkshire Museum

Crane Museum of Papermaking

Tannery Falls

St Mary's of the Assumption Church

Zoar Outdoor/Deerfield Valley Canopy Tours

Top Windsor Hotel Reviews

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

Vacation Village in the Berkshires

The Yankee Inn

Berkshire Mountain Lodge

Hotel Downstreet, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

Berkshires Untold

Jiminy Peak Mountain Resort

More cheap stays in Windsor

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Red Roof Inn PLUS+ South Deerfield – Amherst

The Yankee Inn

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

The Whitlock

Hotels in Windsor with star-rating

Find out more about Windsor

Top reasons to visit Windsor

Find great hotels near Windsor

Where to stay near Windsor

Things to do in Windsor

Booking tips and Expedia advantages for Windsor

Find the best attractions near Windsor

Best time to go to Windsor

The nearest major airports for your trip to Windsor

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app