20 Best B&B in Chester, MA - Bed and Breakfast from $119

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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

$105 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

2. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

$160 nightly

Oct 27 - Oct 28

Total with taxes and fees

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 traveler

$270 nightly

Oct 26 - Oct 27

Total with taxes and fees

4. The Inn at Stockbridge

Stockbridge

Kimberly

$383 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

5. Chambery Inn

Lee

Alexandra

$264 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

6. Devonfield Inn B&B

Lee

Sebastien

$369 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

7. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

$149 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

$393 nightly

Nov 7 - Nov 8

Total with taxes and fees

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Top Chester Hotel Reviews

The Red Lion Inn

8/10 Good

"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"

Blue A Modern Hotel, an Ascend Collection Hotel

8/10 Good

"Close proximity to a great restaurant. Massage chairs were a nice feature but ours didn’t work. Floor was not exactly clean and the soap dispenser was broken. The continental breakfast was just danish and coffee with a few little refrigerator items. Other than that, it wasn’t bad. It was modern and made a good first impression."

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	$119
Highest Price	$616

Frequently asked questions

What is the nightly rate for a B&B in Chester?

Prices for B&Bs in Chester often vary, but you can find a great deal from $119 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

When is the best time to book a B&B in Chester?

The best time to book a B&B in Chester is during the summer months, particularly from June to August. This vibrant season attracts visitors eager to enjoy the picturesque lakes, hiking trails, and outdoor activities that Chester has to offer. With warm weather and long daylight hours, it's an ideal time for families and adventure seekers to explore the natural beauty of the area.

July stands out as the peak month, bringing a lively atmosphere filled with community events, festivals, and a bustling local scene. Travelers can partake in activities such as kayaking on Lake Almanor or hiking in the nearby Lassen National Forest, all while basking in pleasant temperatures that typically range from the mid-60s to high 80s Fahrenheit.

If you're looking for a more budget-friendly option, consider visiting in September. This transitional month allows you to enjoy milder weather and fewer crowds, making it great for a peaceful getaway. You can still experience the stunning scenery, with early fall colors beginning to emerge, creating an enchanting backdrop for outdoor adventures.

What is the difference between a Chester B&B and a hotel?

Every Chester B&B has its own unique feel. 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 home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.

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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 Red Lion Inn

Blue A Modern Hotel, an Ascend Collection Hotel

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

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Chester Bed & Breakfast

Bundle & Save

OneKeyCash

Upfront pricing

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 Red Lion Inn

Find out more about Chester

Chester B&B information

Frequently asked questions

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