Find 3 Star Hotels in Windsor, MA from $109

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November 2026

December 2026

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Our top choices for Windsor 3-star hotels

1. Vacation Village in the Berkshires

Williamstown

Carol

$128 nightly

Nov 11 - Nov 12

Total with taxes and fees

2. Berkshire Mountain Lodge

Pittsfield

Susan J

$108 nightly

Dec 9 - Dec 10

Total with taxes and fees

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

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

South Lee

Michael

$128 nightly

Nov 11 - Nov 12

Total with taxes and fees

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

4. Hotel On North

Pittsfield

Philip

$112 nightly

Nov 29 - Nov 30

Total with taxes and fees

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

5. Hotel Downstreet, an Ascend Collection Hotel

North Adams

marwan

$119 nightly

Nov 24 - Nov 25

Total with taxes and fees

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

6. The Red Lion Inn

Stockbridge

Lisabeth

$197 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

7. Berkshires Untold

Lenox

Brian

$118 nightly

Nov 17 - Nov 18

Total with taxes and fees

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

Gustavo

$107 nightly

Dec 6 - Dec 7

Total with taxes and fees

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

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

$178 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

10. Jiminy Peak Mountain Resort

Hancock

Olga

$130 nightly

Nov 20 - Nov 21

Total with taxes and fees

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

11. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

$126 nightly

Nov 15 - Nov 16

Total with taxes and fees

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

12. The Porches Inn at Mass MoCA

North Adams

Ram

$189 nightly

Dec 9 - Dec 10

Total with taxes and fees

A fire feature with a metal frame and a brick wall in the background.

13. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

$153 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

14. Element by Marriott Lenox Berkshires

Lenox

Francis

$135 nightly

Nov 29 - Nov 30

Total with taxes and fees

A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

$98 nightly

Dec 11 - Dec 12

Total with taxes and fees

A hotel patio with outdoor seating and a fire pit.

16. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

$119 nightly

Nov 15 - Nov 16

Total with taxes and fees

A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.

17. The Ponds at Foxhollow

Lenox

Anthony

A two-story house with a porch, a balcony, and a chimney.

18. Blooming Inn

Shelburne Falls

Robert

$126 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

19. The Revival House

Adams

Ruby

$150 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

20. Inn at Silver Maple Farm

East Chatham

Linda

$164 nightly

Dec 3 - Dec 4

Total with taxes and fees

Top Windsor Hotel Reviews

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

The Revival House

Adams

10/10 Excellent

Ruby

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Excellent

Diane

Blooming Inn

Shelburne Falls

10/10 Excellent

Philip M

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

10/10 Excellent

Gipsy

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

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

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Lloyd A.

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 $109

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.

Find 3 Star Hotels in Windsor, MA from $109

Check prices for these dates

Our top choices for Windsor 3-star hotels

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

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

4. Hotel On North

5. Hotel Downstreet, an Ascend Collection Hotel

6. The Red Lion Inn

7. Berkshires Untold

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

9. The Cornell Inn, Lenox & The Berkshires

10. Jiminy Peak Mountain Resort

11. Courtyard by Marriott Lenox Berkshires

12. The Porches Inn at Mass MoCA

13. Fairfield Inn & Suites by Marriott Williamstown

14. Element by Marriott Lenox Berkshires

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

16. Hilton Garden Inn Lenox Pittsfield

17. The Ponds at Foxhollow

18. Blooming Inn

19. The Revival House

20. Inn at Silver Maple Farm

Top Windsor Hotel Reviews

Hotel On North

10/10 Excellent

Find out more about Windsor

Three Star Hotel Guide for Windsor

Frequently Asked Questions

How much does it cost to stay in a 3-star hotel in Windsor?

What is the difference between a 4-star and 3-star hotel in Windsor?

What is the difference between a 3-star hotel and a motel in Windsor?

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