Find a Bed and Breakfast in Chester from CA $107

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Chester B&B

Bromley View Inn
Relax in this inviting lounge area with a comfortable sofa, wooden bench, and large window offering a view of the outdoors.

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (370)
"After working an entire weekend with festivities in the area checking into here for some much needed rest was the best decision we made very comfortable very nice and very clean "
The price is CA $132
CA $145 total
includes taxes & fees
Aug 5 - Aug 6
Bromley View Inn
The Jackson
Step out onto the covered porch, surrounded by lush greenery and a brick pathway leading to the house.

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (223)
"A quaint boutique historic hotel with a cool little bar and fine dining. The view from our room overlooking the garden and lush lawn added to the tranquil atmosphere that we were hoping for. The owners were pleasant and friendly. "
The price is CA $291
CA $320 total
includes taxes & fees
Aug 5 - Aug 6
The Jackson
The Inn at Manchester
Two-story house surrounded by lush greenery and trees, with a red barn-like structure and a white house.

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (250)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is CA $205
CA $225 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Manchester
The Inn at Ormsby Hill
Stately two-story house with a traditional entrance, surrounded by a well-maintained lawn and mature trees.

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (130)
"beautiful grounds, plentiful outdoor seating, excellent breakfasts"
The price is CA $288
CA $317 total
includes taxes & fees
Aug 5 - Aug 6
The Inn at Ormsby Hill
Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (38)
"Superb stay in all ways!"
The price is CA $343
CA $378 total
includes taxes & fees
Aug 7 - Aug 8
Stay At Jimmy's
Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is CA $193
CA $211 total
includes taxes & fees
Aug 7 - Aug 8
Colonel Williams Inn
The Vesper
Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (26)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is CA $244
CA $269 total
includes taxes & fees
Aug 18 - Aug 19
The Vesper
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is CA $237
CA $258 total
includes taxes & fees
Sep 3 - Sep 4
The Carriage Barn Inn
Blue Gentian Lodge at Magic Mountain
Surrounded by a dense forest, this serene lakeside setting offers a peaceful escape.

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (103)
"The most comfortable stay I have had in a long time. I look forward to visiting the Blue Gentian Lodge again!"
The price is CA $178
CA $196 total
includes taxes & fees
Aug 5 - Aug 6
Blue Gentian Lodge at Magic Mountain
Harvest Barn Inn
Enjoy a serene lake view from the balcony, where two Adirondack chairs await.

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
The price is CA $188
CA $205 total
includes taxes & fees
Aug 18 - Aug 19
Harvest Barn Inn
Stone Hearth Inn and Eatery
Traditional home with a charming porch surrounded by lush gardens and a brick chimney.

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"Sweet place to stay"
The price is CA $278
CA $303 total
includes taxes & fees
Aug 6 - Aug 7
Stone Hearth Inn and Eatery
Inn on Putney Road
Classic two-story house with a gabled roof and symmetrical facade, surrounded by a well-maintained garden and a white fence.

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is CA $406
CA $447 total
includes taxes & fees
Aug 5 - Aug 6
Inn on Putney Road
Deerfield Valley Inn
Surrounded by snow-covered trees, this serene winter scene offers a peaceful retreat.

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (54)
"I liked that it was right on the scenic route"
The price is CA $107
CA $156 total
includes taxes & fees
Aug 20 - Aug 21
Deerfield Valley Inn
Windham Hill Inn
Guests can enjoy a serene view of the surrounding landscape from this outdoor deck.

Windham Hill Inn

4.0 star property
8.4 out of 10, Very good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is CA $250
CA $273 total
includes taxes & fees
Aug 7 - Aug 8
Windham Hill Inn
Chesterfield Inn
Cozy living room with a rustic fireplace, large windows, and classic furnishings.

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is CA $415
CA $450 total
includes taxes & fees
Aug 5 - Aug 6
Chesterfield Inn
Big Bears Lodge
Explore a unique rock formation amidst lush greenery and vibrant flowers.

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"So close to Mount snow it’s a great place to stay "
The price is CA $230
CA $253 total
includes taxes & fees
Aug 5 - Aug 6
Big Bears Lodge
The Buckmaster Inn
Charming two-story house with a welcoming front porch and a red door.

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
The One Cat B&B
Stroll through the serene garden, surrounded by vibrant blooms and a whimsical cat-themed sign.

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is CA $257
CA $283 total
includes taxes & fees
Aug 27 - Aug 28
The One Cat B&B
Woodbridge Inn
Cozy home with a charming porch, blue door, and string lights.

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
Woodbridge Inn
Echo Lake Inn
Relax by the pool surrounded by a charming white picket fence and comfortable lounge chairs.

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is CA $280
CA $306 total
includes taxes & fees
Aug 12 - Aug 13
Echo Lake 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

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent
"So happy we found this hotel. Our second stay in 3 weeks. Great location, very comfortable and clean. Staff is wonderful. "
Joseph 1-night trip
Posted 1 day ago
Keene Elm City Hotel, Ascend Hotel Collection