Chester B&B: Find the Best Bed and Breakfast from CA $167

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Our top choices for Chester bed & breakfast

A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

1. Naomi's Inn Bed & Breakfast

Liberty Heights

Peter

CA $167 total

includes taxes & fees

Oct 29 - Oct 30

A snow-covered outdoor area with a patio, seating, and a covered dining area.

2. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $247 total

includes taxes & fees

Oct 27 - Oct 28

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

3. The Red Door B&B

Lee

Anonymous traveller

CA $392 total

includes taxes & fees

Oct 26 - Oct 27

4. The Inn at Stockbridge

Stockbridge

Kimberly

CA $601 total

includes taxes & fees

Nov 12 - Nov 13

A two-story building with a sign reading "Chambéry Inn".

5. Chambery Inn

Lee

Alexandra

CA $351 total

includes taxes & fees

Nov 17 - Nov 18

A large, two-story house with a well-maintained lawn and a fence.

6. Devonfield Inn B&B

Lee

Sebastien

CA $577 total

includes taxes & fees

Nov 2 - Nov 3

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

7. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

CA $232 total

includes taxes & fees

Oct 25 - Oct 26

A two-story house with a brick entrance and a white facade.

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

Stockbridge

Philippe

CA $576 total

includes taxes & fees

Nov 7 - Nov 8

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Top Chester Hotel Reviews

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

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."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"The first thing I noticed was how nice and helpful the staff was. Everyone was very friendly and quick to offer assistance. The hotel itself and our room were very clean and well maintained and the breakfast was delicious. I plan to stay here whenever we are in the area."

Find out more about Chester

Chester B&B information

Number of reviews	3,414
Accommodation	30 B&B
Lowest Price	CA $167
Highest Price	CA $862

Frequently asked questions

Searching for B&Bs in Chester?

If you're looking for something a little different than your standard hotel experience, a bed and breakfast could be the perfect alternative for your getaway. While you're enjoying your trip to Chester, you might want to explore the theater scene by catching a show at Chester Town Hall.

Why would you choose B&Bs instead of traditional hotels?

Every B&B has its own unique feel. Whether it's a garden for guests to admire or a sunlit breakfast nook, the little details are what make bed and breakfasts the perfect escape.

What are the best B&Bs in Chester?

Here are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 16.6 mi (26.7 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. 14.1 mi (22.7 km) from the heart of downtown. Enjoy the private yard and deli. Whistler's Inn Bed & Breakfast: 14 rooms. Located 16.6 mi (26.7 km) from the core of Chester. Enjoy the private yard and unique décor.

When should I book my B&B in Chester?

When you're planning your escape to Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

What is there to do in Chester?

If you want to check out some popular attractions in Chester, you might enjoy a visit to Chester Town Hall. Glendale Falls and Pyramid Lake are also some sites to visit if you want to see more of the area.

How can I get to and around Chester?

You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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The Berkshires Vacation Rentals

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Naomi's Inn Bed & Breakfast

2. The Cornell Inn, Lenox & The Berkshires

3. The Red Door B&B

4. The Inn at Stockbridge

5. Chambery Inn

6. Devonfield Inn B&B

7. Whistler's Inn Bed & Breakfast

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

9. Daniel Stebbins House

10. Experience Timeless Elegance in The Edith Wharton Room!

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

12. Old Mill Inn

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

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

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

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

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

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

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

20. Brook Farm Inn

Top Chester Hotel Reviews

The Yankee Inn

Blue A Modern Hotel, an Ascend Collection Hotel

The Red Lion Inn

Berkshires Untold

Berkshire Mountain Lodge

Tru by Hilton Chicopee Springfield

The Black Swan Lee - Lenox, an Ascend Collection Hotel

D. Hotel Suites & Spa

Hotel Northampton

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Chester from CA $167

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Naomi's Inn Bed & Breakfast

2. The Cornell Inn, Lenox & The Berkshires

3. The Red Door B&B

4. The Inn at Stockbridge

5. Chambery Inn

6. Devonfield Inn B&B

7. Whistler's Inn Bed & Breakfast

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

9. Daniel Stebbins House

10. Experience Timeless Elegance in The Edith Wharton Room!

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

12. Old Mill Inn

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

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

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

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

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

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

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

20. Brook Farm Inn

Top Chester Hotel Reviews

The Yankee Inn

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia