Windsor B&B: Find the Best Bed and Breakfast from CA $224

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Our top choices for Windsor bed & breakfast

1. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

CA $266 total

includes taxes & fees

Sep 22 - Sep 23

2. Harbour House Inn

Cheshire

Gregory

CA $337 total

includes taxes & fees

Sep 14 - Sep 15

3. Shaker Mill Inn

West Stockbridge

Mervin

CA $224 total

includes taxes & fees

Sep 9 - Sep 10

4. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

CA $274 total

includes taxes & fees

Oct 1 - Oct 2

5. Chambery Inn

Lee

Alexandra

CA $417 total

includes taxes & fees

Sep 9 - Sep 10

6. Devonfield Inn B&B

Lee

Richard

CA $631 total

includes taxes & fees

Sep 9 - Sep 10

7. Inn at Silver Maple Farm

East Chatham

"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."

Jody

CA $354 total

includes taxes & fees

Sep 9 - Sep 10

8. The Inn at Stockbridge

Stockbridge

Jodi

CA $611 total

includes taxes & fees

Sep 14 - Sep 15

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Perfect stay, no problem situation."

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

10/10 Excellent

"Very clean room the staff were very pleasant. The breakfast was pretty decent. The only issue we had was parking that didn’t seem to be enough spots for the hotel when we came back from a concert at Tanglewood. Every spot at the hotel was taken. Luckily somebody left otherwise the place was great."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Find out more about Windsor

Windsor B&B information

Number of reviews	2,084
Accommodation	46 B&B
Lowest Price	CA $224
Highest Price	CA $836

Frequently asked questions

Searching for B&Bs in Windsor?

If you want to find an accommodation with fewer rooms than the traditional hotel and a cozy 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 comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.

What are the top B&Bs in Windsor?

Here are some 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 décor. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 8.6 mi (13.9 km) from the heart of downtown. Enjoy the unique décor and patio area. Whistler's Inn Bed & Breakfast: 14 rooms. Located 15.8 mi (25.4 km) from the core of Windsor. Enjoy the private yard and unique décor.

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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

How can I get to and around Windsor?

Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the heart of the city. 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. Shaker Mill Inn

4. Whistler's Inn Bed & Breakfast

5. Chambery Inn

6. Devonfield Inn B&B

7. Inn at Silver Maple Farm

8. The Inn at Stockbridge

9. Experience Timeless Elegance in The Edith Wharton Room!

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

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

12. The Cornell Inn, Lenox & The Berkshires

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

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

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

16. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

17. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

18. Elegant suite with a king bed, fireplace, and kitchenette.

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

20. Brook Farm Inn

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

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

The Williams Inn

FairBridge Inn Express

Jiminy Peak Mountain Resort

Quality Inn Lee - Lenox South

The Whitlock

Berkshire Mountain Lodge

Hotel On North

Find out more about Windsor

Windsor B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Windsor from CA $224

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. Shaker Mill Inn

4. Whistler's Inn Bed & Breakfast

5. Chambery Inn

6. Devonfield Inn B&B

7. Inn at Silver Maple Farm

8. The Inn at Stockbridge

9. Experience Timeless Elegance in The Edith Wharton Room!

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

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

12. The Cornell Inn, Lenox & The Berkshires

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

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

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

16. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

17. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

18. Elegant suite with a king bed, fireplace, and kitchenette.

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

20. Brook Farm Inn

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Find out more about Windsor

Windsor B&B information

Frequently asked questions

Explore a world of travel with Expedia