Lodging Image

Search Bed and Breakfasts in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

Our top choices for Chester bed & breakfast

Exterior

1. 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)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
The price is ₹15,544
₹17,829 total
includes taxes & fees
7 Sept - 8 Sept
The Cornell Inn, Lenox & The Berkshires
Front of property

2. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 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 ₹25,513
₹28,498 total
includes taxes & fees
7 Sept - 8 Sept
Chambery Inn
Front of property – evening/night

3. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is ₹37,704
₹42,115 total
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B
Property grounds

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is ₹16,754
₹18,715 total
includes taxes & fees
7 Sept - 8 Sept
Whistler's Inn Bed & Breakfast
Front of property

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is ₹35,623
₹41,781 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge
Room (Louis XIV) | Iron/ironing board (on request), free WiFi, individually decorated

6. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (452 reviews)
"Good stay"
United States
Susan
The price is ₹9,922
₹11,257 total
includes taxes & fees
1 Oct - 2 Oct
Naomi's Inn Bed & Breakfast
Exterior

7. Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (55 reviews)
"Great set up and perfect for visiting Mt Holyoke"
United States
David
The price is ₹25,537
₹28,525 total
includes taxes & fees
7 Sept - 8 Sept
Daniel Stebbins House
Suite, Private Bathroom (RedBird Suite) | View from room

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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ₹31,199
₹37,742 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

9. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (536 reviews)
"Great stay from beginning to end!"
United States
Sarah
The price is ₹17,562
₹19,617 total
includes taxes & fees
20 Sept - 21 Sept
Old Mill Inn
Front of property

10. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (173 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ₹23,770
₹27,307 total
includes taxes & fees
17 Sept - 18 Sept
Brook Farm Inn
Exterior

11. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₹22,056
₹23,313 total
includes taxes & fees
7 Sept - 8 Sept
Harbour House 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Great stay, breakfast was ok, busy week loud neighbor. But great place"
Shirlie 3-night trip
Posted 2 hours ago
Tru by Hilton Chicopee Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,538
Accommodation
16 B&B
Lowest Price
₹11,257
Highest Price
₹42,115

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. Whistler's Inn Bed & Breakfast: 14 rooms. 16.6 mi (26.7 km) from the city centre. 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. Becket Land Trust Historic Quarry 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?
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.

Explore a world of travel with Expedia