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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured B&B in Chester

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, (422)
"Simple yet delicious and well executed breakfast. Perfectly cooked eggs. "
United States
Donna
The price is AU$194
includes taxes & fees
14 Dec - 15 Dec
Naomi's Inn Bed & Breakfast
Room, River View (The Williamsburg Suite) | Private kitchen
Old Mill Inn

Old Mill Inn

3.0 star property
Hatfield
9.4 out of 10, Exceptional, (500)
"Loved our stay! "
United States
Jay
Old Mill Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AU$323
includes taxes & fees
4 Dec - 5 Dec
Lakehouse Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is AU$492
includes taxes & fees
24 Dec - 25 Dec
The Inn at Stockbridge
2 Bedrooms 1 Bath
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is AU$334
includes taxes & fees
2 Dec - 3 Dec
Tanglewood Suites
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 AU$509
includes taxes & fees
21 Dec - 22 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Luxury Room, 1 King Bed, Bathtub
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$727
includes taxes & fees
15 Dec - 16 Dec
33 Main
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Business centre
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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AU$705
includes taxes & fees
14 Dec - 15 Dec
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 AU$509
includes taxes & fees
21 Dec - 22 Dec
Experience Timeless Elegance in The Edith Wharton Room!
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is AU$406
includes taxes & fees
11 Dec - 12 Dec
Harbour House Inn
1 bedroom, WiFi, bed sheets
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$630
includes taxes & fees
1 Jan - 2 Jan 2026
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
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$576
includes taxes & fees
21 Dec - 22 Dec
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 AU$609
includes taxes & fees
21 Dec - 22 Dec
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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$876
includes taxes & fees
14 Dec - 15 Dec
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 AU$827
includes taxes & fees
21 Dec - 22 Dec
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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$1,043
includes taxes & fees
14 Dec - 15 Dec
Elegant suite with a king bed, fireplace, and kitchenette.
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$1,043
includes taxes & fees
11 Dec - 12 Dec
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1004)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AU$301
includes taxes & fees
21 Dec - 22 Dec
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

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

10/10 Excellent
"Pleasantly surprised by this hotel. For a budget-friendly option, it was clean, comfortable, and far better than I expected. Great value for the price"
Amanda 2-night trip
Posted 2 days ago
Quality Inn Westfield - Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,601
Accommodation
32 B&B
Lowest Price
AU$194
Highest Price
AU$1,043

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?
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 decor. Chambery Inn: 9 rooms. 14.1 mi (22.7 km) from the city centre. Enjoy the private garden and snack bar/deli. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast 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. Pyramid Lake and Skyline Trail 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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