Find a Bed and Breakfast in Chester from CA $175

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Check prices for these dates

Next weekend
Apr 24 - Apr 26
In two weeks
May 1 - May 3
In one month
May 15 - May 17
In two months
Jun 12 - Jun 14

Our top choices for Chester bed & breakfast

Room (Louis XIV)

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (432 reviews)
"Breakfast was exceptional. We couldn’t have been happier during our stay."
United States
Robert
The price is CA $154
CA $175 total
includes taxes & fees
Apr 16 - Apr 17
Naomi's Inn Bed & Breakfast
Exterior

Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (51 reviews)
"Quaint B&B in the heart of South Hadley. Within walking distance of town and Mount Holyoke College. (Stairs to second floor are a bit steep for anyone with accessibility issues.) Great overall local place to stay. "
United States
Jason
The price is CA $373
CA $416 total
includes taxes & fees
Apr 19 - Apr 20
Daniel Stebbins House
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (505 reviews)
"Quality Inn feeling with wonderful continental breakfast and very clean- well appointed quiet room! Would definitely stay there again on our next visit to Smith College "
United States
Barry
The price is CA $247
CA $276 total
includes taxes & fees
Apr 15 - Apr 16
Old Mill Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $236
CA $263 total
includes taxes & fees
Apr 20 - Apr 21
Chambery Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $313
CA $367 total
includes taxes & fees
Apr 18 - Apr 19
The Inn at Stockbridge
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is CA $412
CA $460 total
includes taxes & fees
Apr 26 - Apr 27
Devonfield Inn B&B
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is CA $324
CA $362 total
includes taxes & fees
May 3 - May 4
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $620
CA $692 total
includes taxes & fees
Apr 26 - Apr 27
33 Main
Suite, Private Bathroom (RedBird Suite) | View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $427
CA $516 total
includes taxes & fees
Apr 27 - Apr 28
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $297
CA $385 total
includes taxes & fees
May 3 - May 4
Experience Timeless Elegance in The Edith Wharton Room!
Interior

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is CA $363
CA $470 total
includes taxes & fees
May 3 - May 4
Elegant Carriage House room with a queen bed and private patio.
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $297
CA $385 total
includes taxes & fees
May 3 - May 4
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $322
CA $340 total
includes taxes & fees
Apr 20 - Apr 21
Harbour House Inn
Interior

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is CA $385
CA $499 total
includes taxes & fees
May 3 - May 4
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $407
CA $527 total
includes taxes & fees
May 3 - May 4
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, bed sheets

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

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is CA $507
CA $660 total
includes taxes & fees
May 6 - May 7
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $551
CA $700 total
includes taxes & fees
May 4 - May 5
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace

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

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is CA $617
CA $798 total
includes taxes & fees
May 3 - May 4
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $617
CA $798 total
includes taxes & fees
May 3 - May 4
Elegant suite with a king bed, fireplace, and kitchenette.
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is CA $178
CA $205 total
includes taxes & fees
May 7 - May 8
The Cornell Inn, Lenox & The Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Fine rooms and bathrooms, good dinner, and excellent common space. Kind of new and funky old school at the same time. I’d stay here next time I’m in the area."
Daniel 1-night trip
Posted 4 hours ago
Berkshires Untold

Find out more about Chester

Chester B&B information

Number of reviews
2,839
Accommodation
30 B&B
Lowest Price
CA $175
Highest Price
CA $798

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?
Below 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 décor. Lakehouse Inn: 14 rooms. Situated 14.8 mi (23.9 km) from the heart of Chester. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. Located 14.1 mi (22.7 km) from the core of Chester. Enjoy the private yard and deli.
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. Pyramid Lake and Jacob's Pillow 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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