Search B&B in Chester

Start date: Check-in selected.
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
Sep 26 - Sep 28
In two weeks
Oct 3 - Oct 5
In one month
Oct 17 - Oct 19
In two months
Nov 14 - Nov 16

B&B in Chester

Our top choices for Chester bed & breakfast

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (380)
"Staff was friendly, room was clean, location the breakfast was okay, was expecting more being that is is referred as a B&B"
The price is ₩162,807
₩179,085 total
includes taxes & fees
Sep 16 - Sep 17
Bromley View Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (230)
"Great stay! "
The price is ₩330,506
₩363,550 total
includes taxes & fees
Sep 17 - Sep 18
The Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (254)
"Friendly staff and very nice breakfast. "
The price is ₩319,845
₩351,843 total
includes taxes & fees
Sep 21 - Sep 22
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, (137)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is ₩319,148
₩351,062 total
includes taxes & fees
Sep 16 - Sep 17
The Inn at Ormsby Hill
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (32)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is ₩235,180
₩258,697 total
includes taxes & fees
Sep 16 - Sep 17
The Vesper
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"We had a lovely time staying here. "
The price is ₩104,094
₩152,829 total
includes taxes & fees
Sep 18 - Sep 19
Deerfield Valley Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (95)
"Sweet place to stay"
The price is ₩303,664
₩330,993 total
includes taxes & fees
Sep 16 - Sep 17
Stone Hearth Inn and Eatery
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (318)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
The price is ₩219,501
₩241,451 total
includes taxes & fees
Sep 21 - Sep 22
Colonel Williams Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (107)
"Quaintly decorated. Lisa and Ken were very good hosts. Not a modern high tech property, but very homey and welcoming. "
The price is ₩235,529
₩259,082 total
includes taxes & fees
Sep 16 - Sep 17
Blue Gentian Lodge at Magic Mountain
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (63)
"Owners are warm and welcoming. Home is charming and well decorated, breakfast excellent. "
The Buckmaster Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (228)
"Lovely setting and excellent breakfast. Very friendly owners ."
The price is ₩243,772
₩265,711 total
includes taxes & fees
Sep 22 - Sep 23
Harvest Barn 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 ₩347,021
₩381,724 total
includes taxes & fees
Sep 17 - Sep 18
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, (155)
"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 ₩246,870
₩267,854 total
includes taxes & fees
Sep 16 - Sep 17
The Carriage Barn 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"
The price is ₩614,688
₩676,162 total
includes taxes & fees
Sep 18 - Sep 19
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 ₩263,402
₩287,108 total
includes taxes & fees
Sep 16 - Sep 17
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 ₩285,700
₩314,270 total
includes taxes & fees
Sep 16 - Sep 17
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."
The price is ₩505,982
₩556,586 total
includes taxes & fees
Sep 16 - Sep 17
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, (76)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is ₩418,098
₩459,908 total
includes taxes & fees
Sep 18 - Sep 19
The One Cat B&B
Big Bears Lodge
Garden

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (180)
"So close to Mount snow it’s a great place to stay "
The price is ₩232,393
₩255,639 total
includes taxes & fees
Sep 19 - Sep 20
Big Bears Lodge
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
The price is ₩370,017
₩403,318 total
includes taxes & fees
Sep 16 - Sep 17
Four Columns 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.
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Strongly recommend and will go back again!"
Craig 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
2,551
Accommodation
34 B&B
Lowest Price
₩104,094
Highest Price
₩614,688

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?
Check out this B&B in the surrounding area: Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the downtown core. 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.