Cheshire B&B: Find the Best Bed and Breakfast from CA $249

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

Cheshire

Gregory

CA $350 total

includes taxes & fees

Aug 11 - Aug 12

2. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

CA $335 total

includes taxes & fees

Sep 7 - Sep 8

3. Chambery Inn

Lee

Joseph

CA $423 total

includes taxes & fees

Aug 10 - Aug 11

4. Devonfield Inn B&B

Lee

Francis

CA $609 total

includes taxes & fees

Sep 3 - Sep 4

5. The Inn at Stockbridge

Stockbridge

Michele

CA $649 total

includes taxes & fees

Sep 7 - Sep 8

6. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

CA $274 total

includes taxes & fees

Aug 25 - Aug 26

7. Whistler's Inn Bed & Breakfast

Lenox

Mary

CA $249 total

includes taxes & fees

Aug 26 - Aug 27

8. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

CA $571 total

includes taxes & fees

Aug 25 - Aug 26

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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"It’s low key and chill. I loke that a lot. Great staff."

Jiminy Peak Mountain Resort

8/10 Good

"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good

"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Find out more about Cheshire

Cheshire B&B information

Number of reviews	1,630
Accommodation	45 B&B
Lowest Price	CA $249
Highest Price	CA $1,106

Frequently asked questions

Searching for B&Bs in Cheshire?

If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. When you want to explore some attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.

Why would you choose a B&B versus a traditional hotel?

B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away.

What are the best B&Bs in Cheshire?

Below are some well-liked B&Bs in the area: Harbour House Inn: 6 rooms. 1.2 mi (2 km) from the heart of Cheshire. Enjoy the free full breakfast and unique décor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 4.7 mi (7.5 km) from the core of Cheshire. Enjoy the unique décor and patio area.

What's the best time of year to book my B&B in Cheshire?

When you're planning your stay in Cheshire, 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 Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Cheshire?

When you want to spend some time in the great outdoors, Mount Greylock State Reservation and Cheshire Reservoir are some notable spots. You might also consider a trip to sites like Mount Greylock State Reservation Visitor Center or Susan B. Anthony Birthplace Museum if you have time to see more of the area.

How can I get to and around Cheshire?

Mapping out your trip in and around Cheshire is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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Dalton Vacation Rentals

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

2. The Trail in Adams - Berkshires’ Art Hotel

3. Chambery Inn

4. Devonfield Inn B&B

5. The Inn at Stockbridge

6. The Cornell Inn, Lenox & The Berkshires

7. Whistler's Inn Bed & Breakfast

8. Experience Timeless Elegance in The Edith Wharton Room!

9. 33 Main

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

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

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

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

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

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

16. Brook Farm 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. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

20. Shaker Mill Inn

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee Inn

Jiminy Peak Mountain Resort

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Cheshire from CA $249

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

2. The Trail in Adams - Berkshires’ Art Hotel

3. Chambery Inn

4. Devonfield Inn B&B

5. The Inn at Stockbridge

6. The Cornell Inn, Lenox & The Berkshires

7. Whistler's Inn Bed & Breakfast

8. Experience Timeless Elegance in The Edith Wharton Room!

9. 33 Main

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

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

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

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

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

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

16. Brook Farm 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. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

20. Shaker Mill Inn

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia