𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Windsor from RM283 (2026) - Fully Refundable Options

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Our top choices for Windsor hotels

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.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

RM452

RM505 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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.

2. The Yankee Inn

Lenox

William

RM440

RM491 total

includes taxes & fees

27 Oct - 28 Oct

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

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

3. Harbour House Inn

Cheshire

Gregory

RM1,034

RM1,092 total

includes taxes & fees

29 Sept - 30 Sept

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 hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

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

4. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

RM322

RM360 total

includes taxes & fees

29 Sept - 30 Sept

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

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.

A dining area with a wooden table, four chairs, and a framed picture on the wall.

5. The Revival House

Adams

Katrina

RM675

RM754 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

6. FairBridge Inn Express

Pittsfield

William

RM253

RM283 total

includes taxes & fees

29 Sept - 30 Sept

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

Pittsfield

Drew

RM547

RM611 total

includes taxes & fees

5 Oct - 6 Oct

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

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

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.

8. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

RM431

RM481 total

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

A modern hotel building with the name "Hotel Downtown" on the facade.

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

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Alexandra

RM551

RM615 total

includes taxes & fees

14 Oct - 15 Oct

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

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

10. Berkshire Inn

Pittsfield

Kristina

RM350

RM391 total

includes taxes & fees

29 Sept - 30 Sept

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

11. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

RM596

RM666 total

includes taxes & fees

25 Oct - 26 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 garden with a wooden house, a tree, and a person tending to plants.

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

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

12. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

RM713

RM796 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

Pittsfield

Susan

RM420

RM469 total

includes taxes & fees

29 Oct - 30 Oct

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.

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Larry

RM494

RM552 total

includes taxes & fees

20 Oct - 21 Oct

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A white two-story building with a porch, labeled as a motel.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

A hay bale display with pumpkins and scarecrows.

15. Willows Motel Williamstown

Williamstown

Linda

RM422

RM471 total

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

16. The Springs Motel

New Ashford

Elizabeth

RM463

RM508 total

includes taxes & fees

30 Sept - 1 Oct

An outdoor seating area with Adirondack chairs and potted plants.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

17. Cozy Corner Motel

Williamstown

Jonathan

RM359

RM422 total

includes taxes & fees

29 Sept - 30 Sept

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

18. Vacation Village in the Berkshires

Williamstown

Jacob

RM388

RM478 total

includes taxes & fees

30 Sept - 1 Oct

A building with a covered parking area and a grassy front yard.

A motel with multiple rooms, a parking area, and a large tree in the foreground.

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

19. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

RM379

RM423 total

includes taxes & fees

29 Sept - 30 Sept

A garden with a swing set, a blue chair, and a flower bed.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

20. Maple Terrace Motel

Williamstown

Deborah

RM526

RM587 total

includes taxes & fees

29 Sept - 30 Sept

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Top Windsor Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Very nice property excellent to stay with family. Especially if you have little ones with you. Property was clean well maintained. Helpful professional staff."

The Yankee Inn

8/10 Good

"Breakfast was good. Biggest issue was the TV. Thanks to a guest and Geoywho helped me. No documents in the room to explain how to use remote/ TV"

Berkshire Mountain Lodge

8/10 Good

"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The bathroom could use some updating. The staff were very nice."

Berkshires Untold

10/10 Excellent

"Amazing!"

Vacation Village in the Berkshires

8/10 Good

"The temperature in the bedroom was very cold"

Quality Inn Lee - Lenox South

8/10 Good

"Typical every day hotel, but clean and comfortable bed. Water pressure could be better."

The Red Lion Inn

10/10 Excellent

"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

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."

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

RM253

RM283 total

29 Sept - 30 Sept

includes taxes & fees

5.4/10 (911 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

RM322

RM360 total

29 Sept - 30 Sept

includes taxes & fees

7.6/10 Good! (917 reviews)

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

1055 South Street Pittsfield MA

RM420

RM469 total

29 Oct - 30 Oct

includes taxes & fees

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

RM422

RM471 total

4 Oct - 5 Oct

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

RM440

RM491 total

27 Oct - 28 Oct

includes taxes & fees

9.2/10 Wonderful! (1,015 reviews)

The Whitlock

16 Church St Lenox MA

RM565

RM631 total

29 Sept - 30 Sept

includes taxes & fees

8.4/10 Very good! (387 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.

Windsor hotels from RM283

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. Holiday Inn & Suites Pittsfield-Berkshires by IHG

2. The Yankee Inn

3. Harbour House Inn

4. Howard Johnson by Wyndham Lenox

5. The Revival House

6. FairBridge Inn Express

7. Hotel On North

8. Best Western Plus Berkshire Hills Inn & Suites

9. Hotel Downstreet, an Ascend Collection Hotel

10. Berkshire Inn

11. Hilton Garden Inn Lenox Pittsfield

12. The Trail in Adams - Berkshires’ Art Hotel

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

14. Hampton Inn & Suites Berkshires-Lenox

15. Willows Motel Williamstown

16. The Springs Motel

17. Cozy Corner Motel

18. Vacation Village in the Berkshires

19. Howard Johnson by Wyndham Williamstown

20. Maple Terrace Motel

Top Windsor Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Yankee Inn

Berkshire Mountain Lodge

Berkshires Untold

Vacation Village in the Berkshires

Quality Inn Lee - Lenox South

The Red Lion Inn

The Whitlock

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Windsor

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

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

Red Roof Inn PLUS+ South Deerfield – Amherst

The Yankee Inn

The Whitlock

Frequently asked questions

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