𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Windsor (2026)

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Our top choices for Windsor hotels

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

A room with large windows, a red patterned rug, a wooden table with benches, and shelves with figurines.

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

An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

1. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

₹11,317

₹12,641 total

includes taxes & fees

15 Nov - 16 Nov

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

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

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.

2. Hotel On North

Pittsfield

Devon

₹11,877

₹13,267 total

includes taxes & fees

8 Nov - 9 Nov

Two Adirondack chairs facing a river with a forested hill in the background.

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

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

A restaurant interior with white tables, cushioned booths, and a bar area.

3. The Yankee Inn

Lenox

Basil

₹9,126

₹10,194 total

includes taxes & fees

27 Oct - 28 Oct

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

A hallway with a collection of plates on the walls, leading to a staircase.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

4. The Porches Inn at Mass MoCA

North Adams

Ram

₹12,848

₹16,472 total

includes taxes & fees

3 Nov - 4 Nov

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

A spacious living room with a large window, a sofa, a chair, and a dining area.

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.

5. Harbour House Inn

Cheshire

Gregory

₹24,087

₹25,460 total

includes taxes & fees

28 Oct - 29 Oct

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 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.

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

6. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

₹14,352

₹16,031 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

7. Vacation Village in the Berkshires

Williamstown

Luke

₹7,628

₹9,562 total

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 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.

8. FairBridge Inn Express

Pittsfield

Richard

₹6,278

₹7,012 total

includes taxes & fees

8 Nov - 9 Nov

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

A two-story building with a symmetrical facade, large columns, and a central entrance.

9. The Revival House

Adams

Katrina

₹13,109

₹14,642 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

10. Berkshire Mountain Lodge

Pittsfield

Michael

₹8,139

₹11,212 total

includes taxes & fees

22 Nov - 23 Nov

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

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

11. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

₹10,410

₹11,628 total

includes taxes & fees

31 Oct - 1 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.

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

A spacious living room with a large sofa, a coffee table, and a fireplace.

12. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

₹11,268

₹12,586 total

includes taxes & fees

15 Nov - 16 Nov

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

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted 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 featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

13. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

₹7,500

₹8,378 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

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

Pittsfield

Ginger

₹9,020

₹10,075 total

includes taxes & fees

24 Nov - 25 Nov

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

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

A single-story building with a porch, a chimney, and a satellite dish.

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

15. Rodeway Inn

Adams

Joann

₹6,375

₹7,121 total

includes taxes & fees

23 Nov - 24 Nov

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 modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

16. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

₹13,702

₹15,305 total

includes taxes & fees

15 Nov - 16 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 cozy living room with a stone fireplace, comfortable seating, and a television.

17. The Springs Motel

New Ashford

Elizabeth

₹10,040

₹11,014 total

includes taxes & fees

1 Nov - 2 Nov

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

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

18. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

₹11,926

₹13,321 total

includes taxes & fees

1 Nov - 2 Nov

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

19. Blue Vista Motor Lodge

North Adams

William

₹15,721

₹16,618 total

includes taxes & fees

12 Nov - 13 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 a coffee machine, a water dispenser, and a sign indicating the fitness center.

20. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

₹9,264

₹10,348 total

includes taxes & fees

15 Nov - 16 Nov

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"I would definitely go back to this property! Very nice location as well and close to Williams College."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"We enjoyed a delicious home cooked breakfast! The staff was wonderful and very accommodating. Lots of ideas were given to us as to where to visit in the area."

Berkshire Mountain Lodge

10/10 Excellent

"outside view,cleanness,large space"

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

8/10 Good

"all good"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Property is on a little lake and we had a balcony room with view of the lake. I can imagine it must be great to have in the warmer months, but we enjoyed the view nonetheless. Everything was clean, staff was friendly, the restaurant food we sampled was very good, the jet tub was much appreciated, and the location was perfect for exploring all of the quaint towns in the Berkshires. The nightly rate was very reasonable."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great"

The Williams Inn

10/10 Excellent

"The staff and ambience are wonderful!"

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent

"Thank you"

Quality Inn Lee - Lenox South

10/10 Excellent

"A"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

₹6,278

₹7,012 total

8 Nov - 9 Nov

includes taxes & fees

5.4/10 (926 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

₹8,478

₹9,470 total

8 Nov - 9 Nov

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

₹8,796

₹9,826 total

15 Nov - 16 Nov

includes taxes & fees

8.6/10 Excellent! (1,005 reviews)

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

1055 South Street Pittsfield MA

₹9,020

₹10,075 total

24 Nov - 25 Nov

includes taxes & fees

9.2/10 Wonderful! (246 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

₹9,126

₹10,194 total

27 Oct - 28 Oct

includes taxes & fees

The Whitlock

16 Church St Lenox MA

₹12,437

₹13,893 total

17 Nov - 18 Nov

includes taxes & fees

8.4/10 Very good! (405 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 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.

Explore a world of travel with Expedia

Book Hotels in Windsor on Expedia.com

Windsor Hotels from ₹7,012

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 Downstreet, an Ascend Collection Hotel

2. Hotel On North

3. The Yankee Inn

4. The Porches Inn at Mass MoCA

5. Harbour House Inn

6. The Trail in Adams - Berkshires’ Art Hotel

7. Vacation Village in the Berkshires

8. FairBridge Inn Express

9. The Revival House

10. Berkshire Mountain Lodge

11. Hampton Inn & Suites Berkshires-Lenox

12. Hilton Garden Inn Lenox Pittsfield

13. Howard Johnson by Wyndham Lenox

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

15. Rodeway Inn

16. Fairfield Inn & Suites by Marriott Williamstown

17. The Springs Motel

18. Courtyard by Marriott Lenox Berkshires

19. Blue Vista Motor Lodge

20. Best Western Plus Berkshire Hills Inn & Suites

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

The Cornell Inn, Lenox & The Berkshires

Berkshire Mountain Lodge

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

The Williams Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

Quality Inn Lee - Lenox South

More cheap stays in Windsor

FairBridge Inn Express

Red Roof Inn PLUS+ South Deerfield – Amherst

Quality Inn Lee - Lenox South

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

The Yankee Inn

The Whitlock

Frequently asked questions

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