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

A snow-covered forest with a narrow stream running through it.

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Our top choices for Chester bed & breakfast

1. The Cornell Inn, Lenox & The Berkshires

Lenox

FRED

$172 nightly

Sep 7 - Sep 8

Total with taxes and fees

2. Chambery Inn

Lee

Alexandra

$300 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. Devonfield Inn B&B

Lee

Richard

$399 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

$177 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. The Inn at Stockbridge

Stockbridge

Jodi

$396 nightly

Sep 13 - Sep 14

Total with taxes and fees

Room (Louis XIV) | Iron/ironing board (on request), WiFi (free), individually decorated

6. Naomi's Inn Bed & Breakfast

Liberty Heights

Susan

$105 nightly

Oct 1 - Oct 2

Total with taxes and fees

7. Daniel Stebbins House

South Hadley

David

$270 nightly

Sep 7 - Sep 8

Total with taxes and fees

Suite, Private Bathroom (RedBird Suite) | View from room

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

Stockbridge

Philippe

$358 nightly

Sep 28 - Sep 29

Total with taxes and fees

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Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"

The Whitlock

10/10 Excellent

"The Inn was quaint and conveniently situated in downtown Lenox near shops and restaurants and a short drive to Tanglewood. The virtual check-in worked seamlessly, and a friendly, helpful staff member greeted us at the front desk. Our King Room was clean, comfortable and attractive - perfect for our overnight getaway."

D. Hotel Suites & Spa

8/10 Good

"This is a beautiful spot, along the river just outside the city. It’s close to everything but away from the hustle and bustle so it’s quiet and it feels secluded. The property is a bit dated but the rooms are kept up with more modern decor. It was perfect for our stay, and we’ll definitely be back again."

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Find out more about Chester

Chester B&B information

Number of reviews	2,538
Accommodation	30 B&B
Lowest Price	$119
Highest Price	$674

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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Check prices for these dates

Our top choices for Chester bed & breakfast

1. The Cornell Inn, Lenox & The Berkshires

2. Chambery Inn

3. Devonfield Inn B&B

4. Whistler's Inn Bed & Breakfast

5. The Inn at Stockbridge

6. Naomi's Inn Bed & Breakfast

7. Daniel Stebbins House

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

9. Experience Timeless Elegance in The Edith Wharton Room!

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

11. Old Mill Inn

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

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

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

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

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

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

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

19. Brook Farm Inn

20. Harbour House Inn

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Whitlock

D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

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

Berkshire Mountain Lodge

Candlewood Suites West Springfield by IHG

Quality Inn West Springfield

The Red Lion Inn

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. The Cornell Inn, Lenox & The Berkshires

2. Chambery Inn

3. Devonfield Inn B&B

4. Whistler's Inn Bed & Breakfast

5. The Inn at Stockbridge

6. Naomi's Inn Bed & Breakfast

7. Daniel Stebbins House

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

9. Experience Timeless Elegance in The Edith Wharton Room!

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

11. Old Mill Inn

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

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

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

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

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

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

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

19. Brook Farm Inn

20. Harbour House Inn

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia