Windsor Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Windsor hotels

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

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

1. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

Rp2.133.561

Rp2.383.187 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.

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

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

2. Vacation Village in the Berkshires

Williamstown

Denton

Rp1.438.042

Rp1.802.645 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

3. The Yankee Inn

Lenox

Basil

Rp1.897.294

Rp2.119.278 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

4. Hotel On North

Pittsfield

Lawrence

Rp2.400.256

Rp2.681.087 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 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.

5. FairBridge Inn Express

Pittsfield

William

Rp1.111.528

Rp1.241.577 total

includes taxes & fees

11 Oct - 12 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.

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

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

6. The Porches Inn at Mass MoCA

North Adams

Ram

Rp2.659.255

Rp3.370.251 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

7. Berkshire Mountain Lodge

Pittsfield

marilyn

Rp1.534.348

Rp2.113.730 total

includes taxes & fees

9 Nov - 10 Nov

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

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

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

Rp2.288.924

Rp2.556.729 total

includes taxes & fees

1 Nov - 2 Nov

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

A gazebo in a garden with a house in the background.

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.

9. Harbour House Inn

Cheshire

Gregory

Rp4.540.976

Rp4.799.811 total

includes taxes & fees

27 Oct - 28 Oct

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

A sauna room with wooden walls, a bench, a heater, and a door leading to an outdoor area.

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.

10. Blue Vista Motor Lodge

North Adams

Vincent

Rp3.831.436

Rp4.049.828 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

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

Pittsfield

Ginger

Rp1.772.001

Rp1.979.325 total

includes taxes & fees

9 Nov - 10 Nov

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 sofa, a coffee table, and a large window with a view of trees.

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.

12. Berkshires Untold

Lenox

Madhavi R

Rp2.330.256

Rp2.602.896 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

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

13. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

Rp2.723.333

Rp3.041.963 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

Rp2.038.696

Rp2.277.223 total

includes taxes & fees

7 Nov - 8 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.

15. The Revival House

Adams

Katrina

Rp2.686.282

Rp3.000.409 total

includes taxes & fees

2 Nov - 3 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.

16. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

Rp1.673.199

Rp1.868.964 total

includes taxes & fees

1 Nov - 2 Nov

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.

An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

17. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

Rp1.754.102

Rp1.959.332 total

includes taxes & fees

7 Nov - 8 Nov

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

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

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

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

Tracy

Rp2.248.293

Rp2.511.344 total

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

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

19. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

Rp3.109.951

Rp3.473.815 total

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 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.

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

20. Howard Johnson by Wyndham Lenox

Lenox

Mark

Rp1.414.021

Rp1.579.461 total

includes taxes & fees

21 Oct - 22 Oct

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Top Windsor Hotel Reviews

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."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Property was clean, staff was knowledgeable and cordial. Parking was very easy."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"no comment"

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 Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

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

Rp1.111.528

Rp1.241.577 total

11 Oct - 12 Oct

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

Rp1.414.021

Rp1.579.461 total

21 Oct - 22 Oct

includes taxes & fees

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

Rp1.598.381

Rp1.785.392 total

1 Nov - 2 Nov

includes taxes & fees

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

1055 South Street Pittsfield MA

Rp1.772.001

Rp1.979.325 total

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (232 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

Rp1.897.294

Rp2.119.278 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

The Whitlock

16 Church St Lenox MA

Rp2.595.355

Rp2.899.011 total

3 Nov - 4 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.

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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Find hotels in Windsor, MA from Rp1.241.577

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. Vacation Village in the Berkshires

3. The Yankee Inn

4. Hotel On North

5. FairBridge Inn Express

6. The Porches Inn at Mass MoCA

7. Berkshire Mountain Lodge

8. Hilton Garden Inn Lenox Pittsfield

9. Harbour House Inn

10. Blue Vista Motor Lodge

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

12. Berkshires Untold

13. Fairfield Inn & Suites by Marriott Williamstown

14. Hampton Inn & Suites Berkshires-Lenox

15. The Revival House

16. Best Western Plus Berkshire Hills Inn & Suites

17. Holiday Inn & Suites Pittsfield-Berkshires by IHG

18. Courtyard by Marriott Lenox Berkshires

19. The Trail in Adams - Berkshires’ Art Hotel

20. Howard Johnson by Wyndham Lenox

Top Windsor Hotel Reviews

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

The Yankee Inn

Jiminy Peak Mountain Resort

Hotel Downstreet, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Cornell Inn, Lenox & The Berkshires

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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