Windsor Hotels from €62 - Fully Refundable Options

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Our top choices for Windsor hotels

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

1. FairBridge Inn Express

Pittsfield

William

€62

includes taxes & fees

11 Oct - 12 Oct

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

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

2. Rodeway Inn

Adams

Joann

€67

includes taxes & fees

2 Nov - 3 Nov

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

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

3. The Yankee Inn

Lenox

Basil

€106

includes taxes & fees

1 Nov - 2 Nov

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

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

Pittsfield

Ginger

€99

includes taxes & fees

9 Nov - 10 Nov

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

€150

includes taxes & fees

2 Nov - 3 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 compact living space with a kitchenette, a dining area, and a sofa.

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

6. The Central Downtown Inn & Suites

Pittsfield

Rena

€99

includes taxes & fees

20 Oct - 21 Oct

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

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.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

7. Hotel On North

Pittsfield

Lawrence

€134

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

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.

8. Howard Johnson by Wyndham Lenox

Lenox

Mark

€79

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

9. Berkshire Inn

Pittsfield

Kristina

€86

includes taxes & fees

19 Oct - 20 Oct

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

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

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

10. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

€114

includes taxes & fees

7 Nov - 8 Nov

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

A kitchen with a fireplace, dining area, and a large window with curtains.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

11. Williamstown Motel

Williamstown

Ahmet

€80

includes taxes & fees

1 Nov - 2 Nov

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

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.

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

€98

includes taxes & fees

7 Nov - 8 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 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.

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

13. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

€173

includes taxes & fees

1 Nov - 2 Nov

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

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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".

14. Berkshire Mountain Lodge

Pittsfield

marilyn

€105

includes taxes & fees

9 Nov - 10 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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

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.

15. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

€93

includes taxes & fees

1 Nov - 2 Nov

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 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.

16. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

€128

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

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

17. Vacation Village in the Berkshires

Williamstown

Denton

€90

includes taxes & fees

1 Nov - 2 Nov

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.

18. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

€119

includes taxes & fees

1 Nov - 2 Nov

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

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

A cozy living room with a stone fireplace, comfortable seating, and a television.

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

19. The Springs Motel

New Ashford

Elizabeth

€109

includes taxes & fees

4 Nov - 5 Nov

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

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.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

20. Berkshires Untold

Lenox

Madhavi R

€130

includes taxes & fees

1 Nov - 2 Nov

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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely room, comfortable bed and a nice breakfast."

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

10/10 Excellent

"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."

The Yankee Inn

10/10 Excellent

"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."

Jiminy Peak Mountain Resort

8/10 Good

"The pool and hot tub were not heated enough. We didn't plan to use any other amenities so that was a disappointment. We enjoyed our stay. The room was good as we are our breakfast and dinner in the room. The kitchen was great and equipped with everything we needed."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

€62

11 Oct - 12 Oct

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

€79

18 Oct - 19 Oct

includes taxes & fees

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

€89

1 Nov - 2 Nov

includes taxes & fees

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

1055 South Street Pittsfield MA

€99

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (232 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

€106

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

The Whitlock

16 Church St Lenox MA

€129

1 Nov - 2 Nov

includes taxes & fees

8.4/10 Very good! (395 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.

What are some of the best holiday rentals that Windsor has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Windsor is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. See all 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

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. FairBridge Inn Express

2. Rodeway Inn

3. The Yankee Inn

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

5. The Revival House

6. The Central Downtown Inn & Suites

7. Hotel On North

8. Howard Johnson by Wyndham Lenox

9. Berkshire Inn

10. Hampton Inn & Suites Berkshires-Lenox

11. Williamstown Motel

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

13. The Trail in Adams - Berkshires’ Art Hotel

14. Berkshire Mountain Lodge

15. Best Western Plus Berkshire Hills Inn & Suites

16. Hilton Garden Inn Lenox Pittsfield

17. Vacation Village in the Berkshires

18. Hotel Downstreet, an Ascend Collection Hotel

19. The Springs Motel

20. Berkshires Untold

Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

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

The Yankee Inn

Jiminy Peak Mountain Resort

Quality Inn Lee - Lenox South

The Red Lion Inn

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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