Photo by Elizabeth Massa Peroulakis

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33 Main
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is HK$3,026
per night
5 May - 6 May
33 Main
Devonfield Inn B&B
Front of property – evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is HK$2,180
per night
5 May - 6 May
Devonfield Inn B&B
Daniel Stebbins House
Exterior
Daniel Stebbins House
3.0 star property
10.0 out of 10, Exceptional, (37)
"Beautiful home that provided a relaxed, comfortable stay. If we are in the area again we would definitely return."
The price is HK$2,112
per night
7 May - 8 May
Daniel Stebbins House
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Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
1 bedroom, desk, iron/ironing board, WiFi
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
10.0 out of 10, Exceptional, (6)
The price is HK$3,118
per night
5 May - 6 May
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
The Red Door B&B
Interior
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Exterior
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is HK$2,336
per night
6 May - 7 May
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is HK$1,055
per night
5 May - 6 May
Lakehouse Inn
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is HK$1,869
per night
10 May - 11 May
Chambery Inn
Old Mill Inn
Front of property
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (433)
"We had a corner room #9 which is bright and has a nice view to nature in the morning. It is on the top floor, so you have high ceilings and the the woodwork. Staff is friendly and helpful. As you have the “waterfall” close to the room, you will hear the background noise night and day. It didn’t bother us, sounds a bit like a a/c. Air plugs are provided, which we didn’t use."
The price is HK$1,560
per night
21 May - 22 May
Old Mill Inn
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"This is a charming and very pleasant place to stay."
The price is HK$1,222
per night
7 May - 8 May
Brook Farm Inn
Harbour House Inn
Exterior
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is HK$1,932
per night
6 May - 7 May
Harbour House Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is HK$3,136
per night
4 May - 5 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Naomi's Inn Bed & Breakfast
Individually decorated, individually furnished, iron/ironing board
Naomi's Inn Bed & Breakfast
3.5 star property
9.0 out of 10, Wonderful, (344)
"Very delightful and large room. Innkeeper is very welcoming. Breakfast was great!"
The price is HK$1,375
per night
4 May - 5 May
Naomi's Inn Bed & Breakfast
Eastgate Inn B&B
Porch
Eastgate Inn B&B
2.5 star property
9.0 out of 10, Wonderful, (64)
"The owner, Daliya, is very friendly and helpful, with good advice. We enjoyed the breakfasts."
Eastgate Inn B&B
Federal House Inn
Rollaway beds, free WiFi
Federal House Inn
3.5 star property
9.0 out of 10, Wonderful, (406)
"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."
Federal House Inn
The Ellery
Lobby
The Ellery
3.5 star property
8.8 out of 10, Excellent, (363)
"nice, clean room. friendly staff. "
The price is HK$1,242
per night
5 May - 6 May
The Ellery
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great breakfast. "
The price is HK$953
per night
5 May - 6 May
The Cornell Inn, Lenox
Tanglewood Suites
Property grounds
Tanglewood Suites
2.5 star property
8.0 out of 10, Very good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
Whistler's Inn Bed & Breakfast
Property grounds
Whistler's Inn Bed & Breakfast
3.5 star property
7.6 out of 10, Good, (431)
"Great location, and the staff was extremely helpful with recommendations, breakfast, etc. the property was clean and nice, but a fair bit older than it appears online, fyi"
The price is HK$1,836
per night
5 May - 6 May
Whistler's Inn Bed & Breakfast
Don't see what you're looking for?
See all available properties in Chester
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.

Other property types in Chester

Cozy apartment located in quiet Williamsburg
Fridge, microwave, oven, stovetop
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (33)
"It’s such a cute apartment- I really enjoyed my time there. The property manager gave me all the information I needed, they were very clear and concise. I did not communicate much with the property manager because everything was perfectly fine."
The price is HK$1,172
per night
5 May - 6 May
Cozy apartment located in quiet Williamsburg
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (182)
"We loved our two night stay in the forest :) The house was super clean, well appointed, quiet and relaxing. We didn't have great weather so didn't get to take advantage of the perfect spot on the lake or any of the kayaks or boats, but the location was a great jumping off point for visiting the various Berkshires towns."
Peace and quiet on the lake
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.

Chester B&B information

Number of reviews
3,109
Accommodation
26 B&B
Lowest Price
HK$953
Highest Price
HK$3,136

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 Ellery: 17.3 mi (27.8 km) from the heart of Chester. The Cornell Inn, Lenox: 16.6 mi (26.7 km) from the city centre. Enjoy the free full breakfast 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. Jacob’s Pillow and Otis Reservoir 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.

Recent Hotel Reviews in Chester
Expedia verified reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5/5 Excellent
"Very good. "
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
Posted 8 hours ago
The Yankee, Trademark Collection by Wyndham