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Search B&B in Chester

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Compare 20 B&B in Chester with updated reviews, rates, and availability.

33 Main
Luxury Room, 1 King Bed, Bathtub | 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 NT$12,533
per night
May 12 - May 13
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 NT$9,029
per night
May 5 - May 6
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 NT$8,746
per night
Jun 4 - Jun 5
Daniel Stebbins House
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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
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 NT$4,389
per night
May 5 - May 6
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 NT$7,776
per night
May 10 - May 11
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 NT$6,459
per night
May 12 - May 13
Old Mill Inn
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"Wonderful hospitality. Amazing breakfast. Will be back!!"
The price is NT$5,061
per night
May 7 - May 8
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 NT$8,001
per night
May 7 - May 8
Harbour House Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center
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 NT$13,047
per night
May 5 - May 6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Naomi's Inn Bed & Breakfast
Room (Louis XIV) | 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 NT$5,987
per night
May 8 - May 9
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
Room | 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)
"I liked the location. The room was clean, well appointed. Perfect property to visit my daughter"
The price is NT$5,145
per night
May 6 - May 7
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 NT$3,948
per night
May 12 - May 13
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 NT$7,602
per night
May 5 - May 6
Whistler's Inn Bed & Breakfast
Chesapeake Inn of Lenox
Property grounds
Chesapeake Inn of Lenox
3.0 star property
7.2 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
The Summer White House
Porch
The Summer White House
3.0 star property
The Summer White House
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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

Chester B&B information

Number of reviews
3,073
Accommodation
20 B&B
Lowest Price
NT$3,948
Highest Price
NT$13,047

Frequently asked questions

Searching for B&Bs in Chester?
If you’re looking for something a little different than your standard hotel experience, a bed and breakfast could be the perfect alternative for your getaway. While you’re enjoying your trip to Chester, you might want to explore the theater scene by catching 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 sunlit breakfast nook, the little details are what make bed and breakfasts the perfect escape.
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 downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the heart of downtown. Enjoy the free full breakfast and deli.
When should I 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 temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chester?
If you want to check out 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?
You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. 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, consider renting a car to take in more sights.

Recent reviews of Chester hotels
Expedia verified reviews

The Ellery

The Ellery

5/5 Excellent
"I liked the location. The room was clean, well appointed. Perfect property to visit my daughter"
A verified traveler stayed at The Ellery
Posted 1 day ago
The Ellery