𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Windsor (2026)

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Our top choices for Windsor hotels

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

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.

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

1. Hotel On North

Pittsfield

Lawrence

S$192

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

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

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

2. FairBridge Inn Express

Pittsfield

William

S$89

includes taxes & fees

26 Oct - 27 Oct

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

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

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

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

Pittsfield

Ginger

S$142

includes taxes & fees

10 Nov - 11 Nov

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

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.

A doorway leading to a room with a fireplace, a sofa, and decorative wall sconces.

4. The Revival House

Adams

Katrina

S$215

includes taxes & fees

2 Nov - 3 Nov

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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

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

5. The Yankee Inn

Lenox

Basil

S$152

includes taxes & fees

1 Nov - 2 Nov

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".

A garden with wooden Adirondack chairs and a stone pathway.

A spacious lobby with a fireplace, seating area, and a bar.

6. Berkshire Mountain Lodge

Pittsfield

Kathleen

S$151

includes taxes & fees

9 Nov - 10 Nov

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

A modern apartment with a living room, kitchenette, and dining area.

7. The Central Downtown Inn & Suites

Pittsfield

Rena

S$142

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

8. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

S$171

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

A hotel room with a desk, chair, TV, and a painting on the wall.

A reception desk with a computer, a monitor, and a sign about Choice Privileges.

A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

9. Rodeway Inn

Adams

Joann

S$96

includes taxes & fees

2 Nov - 3 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

10. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

S$157

includes taxes & fees

1 Nov - 2 Nov

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 room with a hanging bed, a white wall, a window, and a door.

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

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

11. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

S$249

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

S$134

includes taxes & fees

10 Nov - 11 Nov

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A residential street with a paved road, a lamp post, and flowering trees.

A motel with a parking lot, a swimming pool, and outdoor seating.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

13. Berkshire Inn

Pittsfield

Linda

S$121

includes taxes & fees

13 Nov - 14 Nov

A conference room with a whiteboard, tables, and chairs.

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

S$147

includes taxes & fees

13 Nov - 14 Nov

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.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

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

15. Vacation Village in the Berkshires

Williamstown

Pofen

S$129

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

16. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

S$113

includes taxes & fees

18 Oct - 19 Oct

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 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.

17. Berkshires Untold

Lenox

Madhavi R

S$186

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

18. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

S$183

includes taxes & fees

1 Nov - 2 Nov

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

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A covered outdoor area with stone pillars and a view of a road and green hills.

19. Courtyard by Marriott Lenox Berkshires

Lenox

S$180

includes taxes & fees

1 Nov - 2 Nov

A patio area with outdoor furniture, a fire pit, and potted plants.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

A poolside area with lounge chairs, umbrellas, and a swimming pool.

20. The Springs Motel

New Ashford

Elizabeth

S$149

includes taxes & fees

1 Nov - 2 Nov

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Amazing pool and great full kitchens in rooms."

Hotel On North

10/10 Excellent

"This is a great hotel.. likely the best place to stay in Pittsfield. Just an overnight stop so not time to get a good read on the area but a good option for the Berkshires if you you don't want to pay the Lenox/Stockbridge premium."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"O"

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

Berkshire Mountain Lodge

10/10 Excellent

"The room was fantastic. Great place to stay in the Berkshires. The hot tub wasn't working, but things happen. Other than that, it was a perfect stay."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"no breakfast"

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"It was good"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

S$89

26 Oct - 27 Oct

includes taxes & fees

5.4/10 (923 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

S$113

18 Oct - 19 Oct

includes taxes & fees

7.6/10 Good! (923 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

S$128

1 Nov - 2 Nov

includes taxes & fees

7.2/10 Good! (1,008 reviews)

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

1055 South Street Pittsfield MA

S$142

10 Nov - 11 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

S$152

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

The Whitlock

16 Church St Lenox MA

S$206

2 Nov - 3 Nov

includes taxes & fees

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 traveller data. Other good options for your visit to the area are Berkshire Mountain Lodge and The Yankee Inn. See all available top hotels, or vacation rentals in Windsor.

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

Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

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 accommodation options 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, Mount Greylock State Reservation Visitor Center and Pontoosuc Lake. You'll also find Swift River and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.

What's the weather like in Windsor?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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Blandford Holiday Rentals

Windsor Hotels from S$89

Change your mind

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. Hotel On North

2. FairBridge Inn Express

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

4. The Revival House

5. The Yankee Inn

6. Berkshire Mountain Lodge

7. The Central Downtown Inn & Suites

8. Hotel Downstreet, an Ascend Collection Hotel

9. Rodeway Inn

10. Hampton Inn & Suites Berkshires-Lenox

11. The Trail in Adams - Berkshires’ Art Hotel

12. Best Western Plus Berkshire Hills Inn & Suites

13. Berkshire Inn

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

15. Vacation Village in the Berkshires

16. Howard Johnson by Wyndham Lenox

17. Berkshires Untold

18. Hilton Garden Inn Lenox Pittsfield

19. Courtyard by Marriott Lenox Berkshires

20. The Springs Motel

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Windsor

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Red Roof Inn PLUS+ South Deerfield – Amherst

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

The Yankee Inn

The Whitlock

Frequently asked questions

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