Search B&B in Chester

Start date: Check-in selected.
To Date
End date: Check-out
    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
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Chester

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (386)
"Breakfast , beverages and hot tub were nice in addition to the family game room area. "
Bromley View Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (234)
"Excellent Vintage style B&B. "
The Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (264)
"Friendly staff and very nice breakfast. "
The price is AED 678
AED 745 total
includes taxes & fees
26 Oct - 27 Oct
The Inn at Manchester
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (33)
"The location is fabulous bc you can walk everywhere once you arrive. Beds were comfortable and great options at breakfast(the oats and fresh strawberries were my favorite)"
The price is AED 758
AED 833 total
includes taxes & fees
29 Oct - 30 Oct
The Vesper
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (140)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is AED 680
AED 748 total
includes taxes & fees
26 Oct - 27 Oct
The Inn at Ormsby Hill
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (326)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is AED 550
AED 605 total
includes taxes & fees
6 Oct - 7 Oct
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (67)
"We had a lovely time staying here. "
Deerfield Valley Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (233)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
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, (96)
"Sweet place to stay"
The price is AED 1,036
AED 1,129 total
includes taxes & fees
1 Oct - 2 Oct
Stone Hearth Inn and Eatery
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (63)
"Elizabeth and Richard are amazing people and welcomed us into their home. The property is beautifully maintained and Elizabeth's cooking is top notch. "
The Buckmaster Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (42)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is AED 1,098
AED 1,208 total
includes taxes & fees
26 Oct - 27 Oct
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, (156)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
The price is AED 697
AED 757 total
includes taxes & fees
1 Oct - 2 Oct
The Carriage Barn Inn
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
9.0 out of 10, Wonderful, (4)
"Great place to stay. People were Friendly and the service was great. The pizza was great and the service was outstanding."
Four Columns Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (108)
"Lisa was great!"
The price is AED 631
AED 694 total
includes taxes & fees
1 Oct - 2 Oct
Blue Gentian Lodge at Magic Mountain
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (66)
"Staff was very friendly and welcoming "
The price is AED 1,890
AED 2,078 total
includes taxes & fees
14 Oct - 15 Oct
Woodbridge 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 AED 666
AED 726 total
includes taxes & fees
21 Oct - 22 Oct
Windham Hill Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (221)
"An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!"
The price is AED 693
AED 762 total
includes taxes & fees
20 Oct - 21 Oct
Deerhill Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (54)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
Inn on Putney Road
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (77)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 1,036
AED 1,139 total
includes taxes & fees
28 Oct - 29 Oct
The One Cat B&B
Big Bears Lodge
Garden

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (181)
"So close to Mount snow it’s a great place to stay "
The price is AED 612
AED 674 total
includes taxes & fees
2 Oct - 3 Oct
Big Bears Lodge
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.
View all properties
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, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Very clean, up to date, affordable"
Daniel 1-night trip
Posted 22 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

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 might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide a unique setting.
What are the top B&Bs in Chester?
Here is a B&B that guests like in the surrounding area: Bromley View Inn: 16 rooms. Located 17.8 mi (28.6 km) from the core of Chester. Enjoy the unique décor and fireplace in the lobby.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your stay in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll be sure to enjoy Chester for its coffeehouses and restaurants. If you're looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like 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 center. Otherwise, look 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, you may want to rent a car for your trip.