Best B&B Chester in 2026

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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

₹11,254 total

includes taxes & fees

28 Oct - 29 Oct

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

2. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

₹16,628 total

includes taxes & fees

28 Oct - 29 Oct

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

₹26,433 total

includes taxes & fees

26 Oct - 27 Oct

4. The Inn at Stockbridge

Stockbridge

Kimberly

₹40,569 total

includes taxes & fees

12 Nov - 13 Nov

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

5. Chambery Inn

Lee

Alexandra

₹23,647 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Devonfield Inn B&B

Lee

Sebastien

₹38,937 total

includes taxes & fees

2 Nov - 3 Nov

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

7. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

₹15,729 total

includes taxes & fees

25 Oct - 26 Oct

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

₹37,677 total

includes taxes & fees

6 Nov - 7 Nov

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Top Chester Hotel Reviews

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	17 B&B
Lowest Price	₹11,254
Highest Price	₹40,569

Frequently asked questions

Searching for B&Bs in Chester?

If you're looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. While you're enjoying your trip to Chester, you might want to explore the theatre scene by watching 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 beautiful breakfast room, the quaint details are what make bed and breakfasts a fun place to get away.

What are the best B&Bs in Chester?

Here are some well-liked B&Bs in the 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 decor. Chambery Inn: 9 rooms. 14.1 mi (22.7 km) from the city centre. Enjoy the private garden and snack bar/deli. Whistler's Inn Bed & Breakfast: 14 rooms. Located 16.6 mi (26.7 km) from the core of Chester. Enjoy the private garden and unique decor.

What's the best time of year to 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

What is there to do in Chester?

If you want to see 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?

Mapping out your trip in and around Chester is easy with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) away from the city centre. 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, you may want to rent a car for your trip.

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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. Old Mill Inn

11. Brook Farm Inn

Top Chester Hotel Reviews

Berkshires Untold

Berkshire Mountain Lodge

The Yankee Inn

Tru by Hilton Chicopee Springfield

The Black Swan Lee - Lenox, an Ascend Collection Hotel

D. Hotel Suites & Spa

Hotel Northampton

Hotel On North

Quality Inn & Suites Northampton - Amherst

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Search Bed and Breakfasts in Chester

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. Old Mill Inn

11. Brook Farm Inn

Top Chester Hotel Reviews

Berkshires Untold

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia