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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Chester bed & breakfast

A two-story house with a porch and a sign indicating it is a vacation rental.

1. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (468 reviews)
"Love the spirit and enthusiasm of the owner. Breakfast was superb! Highly recommend you stay here."
United States
Peter
The price is AU$170
includes taxes & fees
25 Oct - 26 Oct
Naomi's Inn Bed & Breakfast
A snow-covered outdoor area with a patio, seating, and a covered dining area.

2. 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)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is AU$251
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
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

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveller
The price is AU$398
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
Front of property

4. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is AU$610
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A two-story building with a sign reading "Chambéry Inn".

5. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (389 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AU$369
includes taxes & fees
1 Nov - 2 Nov
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

6. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is AU$587
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A garden with a white gazebo, a brick pathway, and various plants and flowers.

7. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (520 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AU$236
includes taxes & fees
24 Oct - 25 Oct
Whistler's Inn Bed & Breakfast
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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AU$553
includes taxes & fees
8 Nov - 9 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A two-story white house with a green door, white picket fence, and white flowering bushes.

9. Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (56 reviews)
"Great set up and perfect for visiting Mt Holyoke"
United States
David
The price is AU$430
includes taxes & fees
26 Oct - 27 Oct
Daniel Stebbins House
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$454
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

11. 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$454
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A view of a red building by a waterway through a window.

12. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (547 reviews)
"This place is all about the location and quality rooms with a view. Both excellent. Made for a perfect stopover on our New England Fall Foliage trip."
United States
John
The price is AU$283
includes taxes & fees
23 Nov - 24 Nov
Old Mill Inn
A porch with a white railing, a potted plant, and a view of a garden.

13. 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$551
includes taxes & fees
1 Nov - 2 Nov
Cozy Carriage House room with a double bed and private balcony
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

14. 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$518
includes taxes & fees
22 Nov - 23 Nov
Elegant Carriage House room with a queen bed and private patio.
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$581
includes taxes & fees
1 Nov - 2 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

16. 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$719
includes taxes & fees
8 Nov - 9 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AU$747
includes taxes & fees
1 Nov - 2 Nov
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

18. 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$852
includes taxes & fees
1 Nov - 2 Nov
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AU$848
includes taxes & fees
22 Nov - 23 Nov
Elegant suite with a king bed, fireplace, and kitchenette.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

20. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AU$321
includes taxes & fees
2 Nov - 3 Nov
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

Berkshires Untold

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!"
Alisha 2-night trip
Posted 4 hours ago
Berkshires Untold

Find out more about Chester

Chester B&B information

Number of reviews
3,414
Accommodation
30 B&B
Lowest Price
AU$170
Highest Price
AU$852

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. Whistler's Inn Bed & Breakfast: 14 rooms. Located 16.6 mi (26.7 km) from the core of Chester. Enjoy the private garden and unique decor.
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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