Windsor Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Windsor hotels

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

1. The Yankee Inn

Lenox

Karen

2.607.400 ₫

2.912.466 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

2. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

2.344.302 ₫

2.618.586 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A multi-story hotel with a brick facade and a flat roof.

A pool area with a glass ceiling, multiple levels, and outdoor seating.

A lobby with three grey armchairs, a small round table with a plant, and a patterned rug.

3. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

3.076.614 ₫

3.436.578 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

4. Vacation Village in the Berkshires

Williamstown

Alex

2.480.670 ₫

3.056.930 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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

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

A garden with wooden Adirondack chairs and a stone pathway.

5. Berkshire Mountain Lodge

Pittsfield

Robert

2.075.473 ₫

2.900.796 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

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

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.

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Basil

3.733.654 ₫

4.170.491 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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

Drew

3.500.300 ₫

3.909.835 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

8. Quality Inn Lee - Lenox South

Lee

Christine

2.859.014 ₫

3.193.518 ₫ total

includes taxes & fees

24 Sept - 25 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 garden with a wooden pergola, potted plants, and a lawn with chairs.

A swimming pool with lounge chairs and a fence.

9. Maple Terrace Motel

Williamstown

Annette

3.259.125 ₫

3.640.573 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A Red Roof Plus hotel with a two-story building, a parking lot with marked handicapped spaces, and a red awning.

A Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.

A hotel reception area with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi.

A bathroom with a white sink, dark wooden vanity, a large mirror, and a shower area.

10. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Joseph

2.576.012 ₫

2.877.405 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

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

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

A hay bale display with pumpkins and scarecrows.

11. Willows Motel Williamstown

Williamstown

Richard

2.699.859 ₫

3.015.603 ₫ total

includes taxes & fees

13 Sept - 14 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 featuring a table and chairs, a kitchenette with a coffee machine, and a television 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.

12. Howard Johnson by Wyndham Lenox

Lenox

irene

2.059.767 ₫

2.300.760 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

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

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.

13. Berkshire Inn

Pittsfield

Ellen

1.905.714 ₫

2.128.683 ₫ total

includes taxes & fees

7 Sept - 8 Sept

An outdoor seating area with Adirondack chairs and potted plants.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

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

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

14. Cozy Corner Motel

Williamstown

Janis

2.299.639 ₫

2.702.989 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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.

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.

15. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

4.632.046 ₫

5.173.995 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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.

16. Blue Vista Motor Lodge

North Adams

Frederic

5.581.151 ₫

5.899.277 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A dining area with large windows, wooden furniture, and a view of a lake.

A lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

James

3.324.308 ₫

3.713.252 ₫ total

includes taxes & fees

24 Sept - 25 Sept

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.

18. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

3.100.199 ₫

3.462.923 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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.

19. FairBridge Inn Express

Pittsfield

ERICIA

1.619.133 ₫

1.808.571 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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

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

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

Pittsfield

Steve

3.076.614 ₫

3.436.682 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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Top Windsor Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Hotel was clean and stag was helpful and friendly."

The Red Lion Inn

10/10 Excellent

"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"

Willows Motel Williamstown

10/10 Excellent

"Employees were very friendly and helpful during check in. The hotel room was clean, comfortable. The continental breakfast offered was fantastic, plenty of fresh fruit, bagels, muffins, etc. Will stay here again!"

Berkshires Untold

10/10 Excellent

"The entry , bar, and dining room along with the outside patio was beautifully done. It made you happy to be there as it was so welcoming. Ample parking space, great amenities, and comfy quiet room made our stay great. The only thing missing was a floor lamp in our room so we couldn’t read at night as the small lamps were dim."

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

10/10 Excellent

"Breakfast was the weakest thing, but it was free, loved the hot tub and having a couch in our room"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely people and place. Breakfast was great and so was the room. Highly recommend."

Hotel On North

8/10 Good

"Nice room! Comfortable bed. Super friendly staff."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Jiminy Peak Mountain Resort

10/10 Excellent

"Nice to have a kitchenette to cook in"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.619.133 ₫

1.808.571 ₫ total

6 Sept - 7 Sept

includes taxes & fees

5.4/10 (890 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.059.767 ₫

2.300.760 ₫ total

9 Sept - 10 Sept

includes taxes & fees

7.6/10 Good! (907 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

2.344.302 ₫

2.618.586 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.4/10 Very good! (1,006 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

2.576.012 ₫

2.877.405 ₫ total

9 Sept - 10 Sept

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.607.400 ₫

2.912.466 ₫ total

28 Sept - 29 Sept

includes taxes & fees

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

1055 South Street Pittsfield MA

3.076.614 ₫

3.436.682 ₫ total

9 Sept - 10 Sept

includes taxes & fees

9.2/10 Wonderful! (182 reviews)

Hotels in Windsor with star rating

Frequently asked questions

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 1.808.571 ₫

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. The Yankee Inn

2. Best Western Plus Berkshire Hills Inn & Suites

3. Holiday Inn & Suites Pittsfield-Berkshires by IHG

4. Vacation Village in the Berkshires

5. Berkshire Mountain Lodge

6. Hotel Downstreet, an Ascend Collection Hotel

7. Hotel On North

8. Quality Inn Lee - Lenox South

9. Maple Terrace Motel

10. Red Roof Inn PLUS+ South Deerfield – Amherst

11. Willows Motel Williamstown

12. Howard Johnson by Wyndham Lenox

13. Berkshire Inn

14. Cozy Corner Motel

15. Courtyard by Marriott Lenox Berkshires

16. Blue Vista Motor Lodge

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

18. Hampton Inn & Suites Berkshires-Lenox

19. FairBridge Inn Express

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

Top Windsor Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

The Red Lion Inn

Willows Motel Williamstown

Berkshires Untold

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

The Cornell Inn, Lenox & The Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Jiminy Peak Mountain Resort

More cheap stays in Windsor

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Best Western Plus Berkshire Hills Inn & Suites

Red Roof Inn PLUS+ South Deerfield – Amherst

The Yankee Inn

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

Hotels in Windsor with star rating

Frequently asked questions

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