Windsor B&B: Best Windsor Bed and Breakfast

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Our top choices for Windsor bed & breakfast

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.

1. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

includes taxes & fees

26 Oct - 27 Oct

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

2. Harbour House Inn

Cheshire

Gregory

includes taxes & fees

29 Oct - 30 Oct

A house with a chimney, surrounded by trees with autumn foliage.

3. UU Rowe Camp and Conference Center

Rowe

Stuart

includes taxes & fees

28 Oct - 29 Oct

A red building with a sign reading "Shaker Mill Inn."

4. Shaker Mill Inn

West Stockbridge

Mahadeva

includes taxes & fees

2 Nov - 3 Nov

5. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Rowe

Benjamin B.

includes taxes & fees

24 Oct - 25 Oct

A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

includes taxes & fees

24 Oct - 25 Oct

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

7. Inn at Silver Maple Farm

East Chatham

Linda

includes taxes & fees

22 Nov - 23 Nov

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

8. The Red Door B&B

Lee

Anonymous traveller

includes taxes & fees

26 Oct - 27 Oct

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Top Windsor Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"Nice modern motel well located for AT hike"

Jiminy Peak Mountain Resort

8/10 Good

"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Find out more about Windsor

Windsor B&B information

Number of reviews	2,864
Accommodation	46 B&B
Lowest Price	AU$161
Highest Price	AU$610

Frequently asked questions

Searching for B&Bs in Windsor?

If you want to find somewhere to stay with fewer rooms than a hotel and a more personalised environment, a B&B may be the perfect thing for your trip to Windsor.

How do you know if a B&B is the right choice for you?

B&Bs all have a unique charm — whether it's a garden for guests to admire or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.

What are the top B&Bs in Windsor?

Here are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 15.6 mi (25.1 km) from the heart of Windsor. Enjoy the free full breakfast and unique decor. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 8.6 mi (13.9 km) from the city centre. Enjoy the unique decor and patio area. Chambery Inn: 9 rooms. Located 17.4 mi (28 km) from the core of Windsor. Enjoy the private garden and snack bar/deli.

When is the best time to book my B&B in Windsor?

When you're planning your escape to Windsor, year-round temperatures and rainfall may be important factors to consider. 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.

How can I get to and around Windsor?

You can map out your trip in and around Windsor ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor bed & breakfast

1. The Trail in Adams - Berkshires’ Art Hotel

2. Harbour House Inn

3. UU Rowe Camp and Conference Center

4. Shaker Mill Inn

5. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

6. Whistler's Inn Bed & Breakfast

7. Inn at Silver Maple Farm

8. The Red Door B&B

9. Chambery Inn

10. The Inn at Stockbridge

11. Cozy Retreat in historic Farmhouse - Tranquility Room

12. The Cornell Inn, Lenox & The Berkshires

13. Cozy Farmhouse Retreat - Ram Dass Room

14. Devonfield Inn B&B

15. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

16. Experience Timeless Elegance in The Edith Wharton Room!

17. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

18. Cozy Carriage House room with a double bed and private balcony

19. Elegant Carriage House room with a queen bed and private patio.

20. Historic Susan B. Anthony Room - Cozy & Charming Stay

Top Windsor Hotel Reviews

Quality Inn Lee - Lenox South

Jiminy Peak Mountain Resort

Berkshires Untold

Berkshire Mountain Lodge

The Whitlock

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Williams Inn

Find out more about Windsor

Windsor B&B information

Frequently asked questions

Explore a world of travel with Expedia

Search Windsor Bed & Breakfast

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor bed & breakfast

1. The Trail in Adams - Berkshires’ Art Hotel

2. Harbour House Inn

3. UU Rowe Camp and Conference Center

4. Shaker Mill Inn

5. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

6. Whistler's Inn Bed & Breakfast

7. Inn at Silver Maple Farm

8. The Red Door B&B

9. Chambery Inn

10. The Inn at Stockbridge

11. Cozy Retreat in historic Farmhouse - Tranquility Room

12. The Cornell Inn, Lenox & The Berkshires

13. Cozy Farmhouse Retreat - Ram Dass Room

14. Devonfield Inn B&B

15. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

16. Experience Timeless Elegance in The Edith Wharton Room!

17. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

18. Cozy Carriage House room with a double bed and private balcony

19. Elegant Carriage House room with a queen bed and private patio.

20. Historic Susan B. Anthony Room - Cozy & Charming Stay

Top Windsor Hotel Reviews

Quality Inn Lee - Lenox South

Find out more about Windsor

Windsor B&B information

Frequently asked questions

Explore a world of travel with Expedia