Windsor Holiday Rentals, Massachusetts: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Windsor

Pet friendly

Apartment

Hot tub

Pool

Condo

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Windsor hotels

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

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

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

1. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

฿4,025

฿4,496 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

John

฿4,224

฿4,718 total

includes taxes & fees

8 Nov - 9 Nov

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

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

3. The Porches Inn at Mass MoCA

North Adams

Ram

฿5,297

฿6,671 total

includes taxes & fees

24 Nov - 25 Nov

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

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

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.

4. The Yankee Inn

Lenox

Basil

฿3,579

฿3,998 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 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.

5. Vacation Village in the Berkshires

Williamstown

Luke

฿2,713

฿3,400 total

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating and a fire pit.

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

A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.

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

6. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,007

฿4,476 total

includes taxes & fees

15 Nov - 16 Nov

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

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

7. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,702

฿4,135 total

includes taxes & fees

2 Nov - 3 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 Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

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

8. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

฿4,873

฿5,443 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

9. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

฿4,241

฿4,737 total

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

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

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

Pittsfield

Ginger

฿3,208

฿3,583 total

includes taxes & fees

24 Nov - 25 Nov

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

A garden with wooden Adirondack chairs and a stone pathway.

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

11. Berkshire Mountain Lodge

Pittsfield

Michael

฿2,894

฿3,987 total

includes taxes & fees

22 Nov - 23 Nov

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

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.

A bedroom with a bed, a sofa, a fireplace, and a chandelier.

12. The Revival House

Adams

Katrina

฿5,067

฿5,660 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 garden with a wooden house, a tree, and a person tending to plants.

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

13. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

฿5,867

฿6,553 total

includes taxes & fees

27 Oct - 28 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 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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

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

14. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,295

฿3,680 total

includes taxes & fees

15 Nov - 16 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 lush garden with flowering plants and a large tree.

15. Harbour House Inn

Cheshire

Gregory

฿8,566

฿9,054 total

includes taxes & fees

28 Oct - 29 Oct

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

16. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

฿2,667

฿2,979 total

includes taxes & fees

27 Oct - 28 Oct

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".

17. Berkshires Untold

Lenox

Madhavi R

฿4,396

฿4,910 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 large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

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

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

18. Blue Vista Motor Lodge

North Adams

William

฿6,138

฿6,488 total

includes taxes & fees

18 Nov - 19 Nov

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A spacious living area with a fireplace, wooden beams, and a large window.

19. The Williams Inn

Williamstown

Pete

฿6,859

฿7,662 total

includes taxes & fees

8 Nov - 9 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 swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

20. Berkshire Inn

Pittsfield

cheryl

฿2,903

฿3,243 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"Room was good. Location was great ! Close to South Deerfield center, close to Rte 116 and I-91. About equidistant from Amherst, Northampton and Greenfield. Electric car charger next door - level 3 in town center. Level 2 in Park and ride. Room clean and upkeep was by request not daily. Free coffee in room."

Berkshire Mountain Lodge

10/10 Excellent

"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every night. If you want an old school meet the other visitors experience, you could probably have it. There is laundry on every floor. I think the awesome prices we got were due to it not being ski season? once we go there and did some driving around we realized Bousquet mountain was right there. So probably a brilliant choice for a long family ski trip. There are a couple of really convenient grocery stores and restaurants right there - but most of the tourist attractions and pittsfield downtown are 10minute or so drive away. Beautiful lobby/property. Enjoyed the coffee machine in the library. Really great experience. We'd love to stay again."

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

10/10 Excellent

"Really excellent spot for families. Loved having a townhouse to spread out and good kitchenette. Amenities were great and helped get little kids energy out."

Hotel On North

10/10 Excellent

"Can't wait to go back!"

Vacation Village in the Berkshires

10/10 Excellent

"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"

Jiminy Peak Mountain Resort

8/10 Good

"Rooms were clean, nice beds and new kitchen accessories."

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."

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

8/10 Good

"all good"

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,401

฿2,681 total

27 Oct - 28 Oct

includes taxes & fees

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

฿3,015

฿3,368 total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,008 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

฿3,128

฿3,494 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

฿3,208

฿3,583 total

24 Nov - 25 Nov

includes taxes & fees

9.2/10 Wonderful! (246 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,579

฿3,998 total

1 Nov - 2 Nov

includes taxes & fees

The Whitlock

16 Church St Lenox MA

฿4,356

฿4,865 total

4 Nov - 5 Nov

includes taxes & fees

8.4/10 Very good! (406 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

More ways to book

Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, MA from ฿2,533

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 Porches Inn at Mass MoCA

4. The Yankee Inn

5. Vacation Village in the Berkshires

6. Hilton Garden Inn Lenox Pittsfield

7. Hampton Inn & Suites Berkshires-Lenox

8. Fairfield Inn & Suites by Marriott Williamstown

9. Courtyard by Marriott Lenox Berkshires

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

11. Berkshire Mountain Lodge

12. The Revival House

13. The Trail in Adams - Berkshires’ Art Hotel

14. Best Western Plus Berkshire Hills Inn & Suites

15. Harbour House Inn

16. Howard Johnson by Wyndham Lenox

17. Berkshires Untold

18. Blue Vista Motor Lodge

19. The Williams Inn

20. Berkshire Inn

Top Windsor Hotel Reviews

Red Roof Inn PLUS+ South Deerfield – Amherst

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Hotel On North

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

The Cornell Inn, Lenox & The Berkshires

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

Hotel Downstreet, an Ascend Collection Hotel

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

Explore a world of travel with Expedia

Go further with the Expedia app