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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Browse Select Chester B&B

Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished
Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (421)
"Simple yet delicious and well executed breakfast. Perfectly cooked eggs. "
United States
Donna
The price is ₹9,927
₹11,262 total
includes taxes & fees
19 Nov - 20 Nov
Naomi's Inn Bed & Breakfast
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels
Old Mill Inn

Old Mill Inn

3.0 star property
Hatfield
9.4 out of 10, Exceptional, (499)
"Loved our stay! "
United States
Jay
The price is ₹34,761
₹38,829 total
includes taxes & fees
22 Nov - 23 Nov
Old Mill Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is ₹15,272
₹17,912 total
includes taxes & fees
20 Nov - 21 Nov
Lakehouse Inn
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is ₹11,990
₹13,393 total
includes taxes & fees
21 Nov - 22 Nov
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is ₹22,231
₹26,074 total
includes taxes & fees
20 Nov - 21 Nov
The Inn at Stockbridge
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
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 ₹37,788
₹42,210 total
includes taxes & fees
23 Nov - 24 Nov
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, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
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 ₹19,412
₹19,412 total
includes taxes & fees
2 Dec - 3 Dec
Tanglewood Suites
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 ₹33,853
₹40,952 total
includes taxes & fees
2 Dec - 3 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 ₹22,087
₹23,346 total
includes taxes & fees
2 Dec - 3 Dec
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.
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Top Chester Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Will recommend"
Dorian 1-night trip
Posted 4 days ago
Tru by Hilton Chicopee Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,317
Accommodation
18 B&B
Lowest Price
₹11,262
Highest Price
₹42,210

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. Whistler's Inn Bed & Breakfast: 14 rooms. Situated 16.6 mi (26.7 km) from the heart of Chester. Enjoy the private garden and unique decor. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and snack bar/deli.
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. Littleville Lake 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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