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Check prices for these dates

Next weekend
5 June - 7 June
In two weeks
12 June - 14 June
In one month
26 June - 28 June
In two months
24 July - 26 July

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, (442 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is AU$186
includes taxes & fees
3 June - 4 June
Naomi's Inn Bed & Breakfast
Exterior

Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (52 reviews)
"Daniel Stebbins House was wonderful. Beautiful rooms. Next to downtown. Enjoyable breakfast. Fabulous experience!"
United States
Holly
The price is AU$420
includes taxes & fees
3 June - 4 June
Daniel Stebbins House
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (509 reviews)
"Nice, quiet, new furnishings, continental breakfast was very fresh, staff is friendly. "
United States
Jeffrey
The price is AU$251
includes taxes & fees
2 June - 3 June
Old Mill Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (377 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 AU$266
includes taxes & fees
2 June - 3 June
Chambery Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AU$512
includes taxes & fees
3 June - 4 June
Devonfield Inn B&B
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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AU$556
includes taxes & fees
14 June - 15 June
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AU$414
includes taxes & fees
7 June - 8 June
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 AU$912
includes taxes & fees
2 June - 3 June
33 Main
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 AU$442
includes taxes & fees
9 June - 10 June
Experience Timeless Elegance in The Edith Wharton Room!
Shower, towels

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AU$447
includes taxes & fees
3 June - 4 June
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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 AU$551
includes taxes & fees
14 June - 15 June
Elegant Carriage House room with a queen bed and private patio.
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 AU$582
includes taxes & fees
4 June - 5 June
Cozy Carriage House room with a double bed and private balcony
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 AU$359
includes taxes & fees
17 June - 18 June
Harbour House Inn
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$611
includes taxes & fees
2 June - 3 June
Historic Susan B. Anthony Room - Cozy & Charming Stay
Shower, towels

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AU$790
includes taxes & fees
2 June - 3 June
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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 AU$736
includes taxes & fees
8 June - 9 June
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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 AU$894
includes taxes & fees
2 June - 3 June
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 AU$894
includes taxes & fees
2 June - 3 June
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, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AU$242
includes taxes & fees
7 June - 8 June
The Cornell Inn, Lenox & The Berkshires
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is AU$253
includes taxes & fees
30 June - 1 July
Brook Farm Inn
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

Riverdale Inn

Riverdale Inn

2/10 Terrible
"I got bitten by insects"
Arquimedes 1-night trip
Posted 1 hour ago
Riverdale Inn

Find out more about Chester

Chester B&B information

Number of reviews
2,810
Accommodation
30 B&B
Lowest Price
AU$186
Highest Price
AU$912

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. Brook Farm Inn: 15 rooms. Located 16.7 mi (26.8 km) from the core of Chester. Enjoy the free cooked breakfast and outdoor pool.
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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