Search B&B in Chester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

Browse Select Chester B&B

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (363)
"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 "
Bromley View Inn
The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (221)
"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 Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (247)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is 4.351.644 ₫
4.787.070 ₫ total
includes taxes & fees
6 Aug - 7 Aug
The Inn at Manchester
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (129)
"The staff was excellent! We would recommend this Inn to anyone!"
The price is 5.201.064 ₫
5.721.171 ₫ total
includes taxes & fees
27 Jul - 28 Jul
The Inn at Ormsby Hill
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (38)
"Superb stay in all ways!"
The price is 5.985.144 ₫
6.583.658 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Stay At Jimmy's
The Carriage Barn Inn
Free daily continental breakfast

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 4.726.355 ₫
5.128.095 ₫ total
includes taxes & fees
28 Jul - 29 Jul
The Carriage Barn Inn
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (24)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is 4.410.450 ₫
4.851.626 ₫ total
includes taxes & fees
30 Jul - 31 Jul
The Vesper
Blue Gentian Lodge at Magic Mountain
Kayaking

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 3.371.544 ₫
3.708.699 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Blue Gentian Lodge at Magic Mountain
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (221)
"Nice and comfortable great breakfast"
Harvest Barn Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (91)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is 5.264.313 ₫
5.738.101 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Stone Hearth Inn and Eatery
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
"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 6.933.097 ₫
7.626.224 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Inn on Putney Road
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is 4.116.420 ₫
4.486.898 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (52)
"Nice room, cozy"
Deerfield Valley Inn
Windham Hill Inn
Mountain view

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 4.939.704 ₫
5.384.277 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Windham Hill Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is 7.870.595 ₫
8.539.677 ₫ total
includes taxes & fees
4 Aug - 5 Aug
Chesterfield Inn
Big Bears Lodge
Garden

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 4.358.178 ₫
4.794.126 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Big Bears Lodge
The One Cat B&B
Exterior

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 5.292.540 ₫
5.821.794 ₫ total
includes taxes & fees
30 Jul - 31 Jul
The One Cat B&B
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Woodbridge Inn
Front of property – evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
Woodbridge Inn
Golden Stage Inn B&B
Seasonal outdoor pool

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Very beautiful place and excellent service "
Golden Stage Inn B&B
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent
"Dillon, your front desk associate was amazing. Easy to work with and extremely accommodating. A real asset to the hotel. "
James 1-night trip
Posted 13 hours ago
Keene Elm City Hotel, Ascend Hotel Collection

Frequently asked questions

Searching for B&Bs in Chester?
If you're hoping for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.
Are you considering an apartment for your stay?
With attentive service, opportunities to meet guests from other places and delectable breakfasts, B&Bs all have a unique setting.
How many bed & breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your getaway in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a getaway to Chester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll definitely enjoy Chester for its coffee shops and restaurants. If you're looking to find something to do during your travels, you might consider visiting DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites such as Vermont Museum of Mining and Minerals or Vermont Country Store if you have time 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 Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city centre. You can also search for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.