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Find a Bed and Breakfast in Chester from CA $156

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Chester B&B

Naomi's Inn Bed & Breakfast
Room (Louis XIV)

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (407)
"We had a great stay and breakfast was delicious!"
The price is CA $156
CA $177 total
includes taxes & fees
Aug 24 - Aug 25
Naomi's Inn Bed & Breakfast
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (46)
"The area is lovely and this building is full of history but they have managed to fit modern air-conditioning into this 226 year old building. "
The price is CA $373
CA $417 total
includes taxes & fees
Aug 19 - Aug 20
Daniel Stebbins House
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (492)
"Very comfortable with excellent service from the staff and owners. Quiet and out of the way yet not far from Amherst and Northampton. Would definitely recommend it and would stay there again."
The price is CA $280
CA $313 total
includes taxes & fees
Aug 19 - Aug 20
Old Mill Inn
The Ellery
Lobby

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (791)
"Great breakfast included in price!"
The price is CA $206
CA $230 total
includes taxes & fees
Aug 19 - Aug 20
The Ellery
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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!! "
The price is CA $344
CA $364 total
includes taxes & fees
Aug 25 - Aug 26
Harbour House Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
The price is CA $311
CA $347 total
includes taxes & fees
Aug 19 - Aug 20
Chambery Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $484
CA $540 total
includes taxes & fees
Aug 26 - Aug 27
Devonfield Inn B&B
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is CA $176
CA $251 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is CA $287
CA $416 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Edith Wharton Room!
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

Elegant Carriage House room with a queen bed and private patio.

The price is CA $309
CA $444 total
includes taxes & fees
Sep 3 - Sep 4
Elegant Carriage House room with a queen bed and private patio.
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The price is CA $287
CA $416 total
includes taxes & fees
Sep 1 - Sep 2
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is CA $331
CA $471 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is CA $353
CA $499 total
includes taxes & fees
Sep 1 - Sep 2
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is CA $452
CA $629 total
includes taxes & fees
Aug 19 - Aug 20
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is CA $497
CA $689 total
includes taxes & fees
Sep 2 - Sep 3
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is CA $563
CA $772 total
includes taxes & fees
Sep 2 - Sep 3
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

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

The price is CA $563
CA $772 total
includes taxes & fees
Sep 1 - Sep 2
Elegant suite with a king bed, fireplace, and kitchenette.
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
The price is CA $240
CA $268 total
includes taxes & fees
Aug 19 - Aug 20
Whistler's Inn Bed & Breakfast
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is CA $838
CA $937 total
includes taxes & fees
Aug 26 - Aug 27
33 Main
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (156)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
The price is CA $327
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"The gentleman at the front desk was amazing. I don’t usually leave reviews but he was possibly the most professional individual that I have met. He made us feel welcome, informed, and comfortable. The hotel exceeded expectations and had everything the tired road travel or couple on a getaway could want."
Tania 1-night trip
Posted 7 hours ago
D. Hotel Suites & Spa