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Find 3 Star Hotels in Windsor, MA from $110

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Check availability on Windsor 3 Star Hotels

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Windsor 3-star hotels

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern hotel building with the name "Hotel Downtown" on the facade.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

1. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Alexandra
$144 nightly
$160 total
Sep 20 - Sep 21
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Sarah
$122 nightly
$136 total
Sep 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
$109 nightly
$121 total
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
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.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

4. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
$136 nightly
$152 total
Sep 14 - Sep 15
Total with taxes and fees
Berkshires Untold
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A backyard with a swimming pool, lounge chairs, and a hot tub.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
$212 nightly
$237 total
Sep 23 - Sep 24
Total with taxes and fees
The Red Lion Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Linda
$135 nightly
$150 total
Sep 16 - Sep 17
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A library with bookshelves, a television, and two armchairs.

7. Hotel On North

Hotel On North
Pittsfield
United States
Drew
$152 nightly
$170 total
Sep 14 - Sep 15
Total with taxes and fees
Hotel On North
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Susan
$125 nightly
$140 total
Sep 21 - Sep 22
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A resort with multiple buildings, a parking area, and a mountainous backdrop.
A wooden cabin with a porch and steps leading to a door, surrounded by snow.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.
A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

9. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
United States
Jacqueline
$159 nightly
$178 total
Sep 14 - Sep 15
Total with taxes and fees
Jiminy Peak Mountain Resort
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.
A buffet area with a counter, food items, and a beverage station.

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
$115 nightly
$128 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

11. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
$172 nightly
$191 total
Sep 14 - Sep 15
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

12. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
$196 nightly
$219 total
Sep 20 - Sep 21
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.
A hallway with a collection of plates on the walls, leading to a staircase.

13. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Cheryl
$206 nightly
$230 total
Sep 15 - Sep 16
Total with taxes and fees
The Porches Inn at Mass MoCA
A fire feature with a metal frame and a brick wall in the background.
A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.
A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.
A reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

14. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
Williamstown
United States
C. David
$180 nightly
$201 total
Sep 20 - Sep 21
Total with taxes and fees
Fairfield Inn & Suites by Marriott Williamstown
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A hotel patio with outdoor seating and a fire pit.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

15. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
$146 nightly
$163 total
Sep 20 - Sep 21
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
An outdoor seating area with Adirondack chairs and a fire feature.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

16. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
$178 nightly
$199 total
Sep 20 - Sep 21
Total with taxes and fees
Element by Marriott Lenox Berkshires
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A wooden interior with a table, chair, and a view of a red barn through an open door.
A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

17. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Jody
$179 nightly
$200 total
Sep 14 - Sep 15
Total with taxes and fees
Inn at Silver Maple Farm
A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.
A serene pond with a stone bridge, surrounded by lush greenery and a house in the background.
A stone bench by a calm lake with a stone wall and grass in the foreground.
A spacious loft-style living room with high ceilings, large windows, and a fireplace.

18. The Ponds at Foxhollow

The Ponds at Foxhollow
Lenox
United States
Aaron
The Ponds at Foxhollow
A living room with a fireplace, two sofas, and four black side tables.
A dining area with a wooden table, four chairs, and a framed picture on the wall.
A two-story building with a symmetrical facade, large columns, and a central entrance.
A bedroom with a bed, a sofa, a fireplace, and a chandelier.

19. The Revival House

The Revival House
Adams
United States
James
$166 nightly
$185 total
Sep 14 - Sep 15
Total with taxes and fees
The Revival House
A garden with a white gazebo, a brick pathway, and various plants and flowers.
A courtyard with stone steps, potted plants, and a small wooden structure.
A breakfast buffet with various dishes and beverages.
A spacious living room with a grand piano, a red armchair, and a chandelier.

20. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
Lenox
United States
Mary Anna
$188 nightly
$210 total
Sep 14 - Sep 15
Total with taxes and fees
Whistler's Inn Bed & Breakfast
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Windsor.
The Williams Inn

The Williams Inn

101 Spring Street Williamstown MA
$183 nightly
$204 total
Sep 20 - Sep 21
Total with taxes and fees
The Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA
$98 nightly
$110 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (410 reviews)
The Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

30 East Street Stockbridge MA
$396 nightly
$442 total
Sep 14 - Sep 15
Total with taxes and fees
9.8/10 Exceptional! (106 reviews)
The Inn at Stockbridge
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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.

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My go-to place for visiting NW MA."
David 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Breakfast room has a wonderful view of the lake. Toaster is difficult to regulate without directions."
Richard 2-night trip
Posted 9 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 9 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 5 days ago
Jiminy Peak Mountain Resort

Find out more about Windsor

Three Star Hotel Guide for Windsor

There’s a reason the top 3 star hotels in Windsor, Massachusetts are so incredibly popular: They combine comforting amenities and just-for-you service with some of the best rates and discounts the area has to offer. When you book a stay at a three star hotel in Windsor, you’ll get access to perfect little perks like on-site restaurants and cocktail bars, well-appointed fitness centers, and spacious rooms.

Search for a cheap deal on a 3 star upscale hotel in Windsor for the most elegant experience, or grab a low rate on one of the cheap 3 star hotels in Windsor near the local attractions, if you want something a touch more unassuming. Whatever your traveling style, make sure to use the search tools at Expedia to track down prices, read more about amenities, and score a few local discounts.

From business trips to family getaways, the Windsor 3 star hotels offer a fantastic home base for any type of vacation.

Frequently asked questions

How much does it cost to stay in a 3-star hotel in Windsor?
Find the perfect trifecta of comfort, affordability and quality at a 3-star hotel in Windsor with our handy filters. Enter your travel dates and then tailor your search based on the amount you want to spend per night.
  • Search for the lowest price per night right now from $110
What is the difference between a 4-star and 3-star hotel in Windsor?
Relaxation comes easy in 3-star hotels in Windsor. On top of cozy surroundings, these more cost-effective properties include a variety of welcome amenities like WiFi, coffee maker and a gym. A 4-star hotel offers a classier experience with enhanced features such as an on-site spa center, pool and more spacious rooms. Regardless of your preferred hotel style or what you want to spend, we have the right option for you.
What is the difference between a 3-star hotel and a motel in Windsor?
Motels usually offer more affordable rates than hotels, which makes them excellent if you're exploring around Windsor and sticking to a budget. A great option for overnight stays, these roadside getaways have simply furnished rooms, basic services and ample parking. Choose a 3-star hotel and you can expect to pay more for additional comfort, privacy and amenities. Travelers can make use of things like a gym, free WiFi and business services at this property type.

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