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Check prices for these dates

Next weekend
19 Sept - 21 Sept
In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Featured 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, (378)
"Small rustic motel with lounge near Bromley winhall etc best prices around and clean overall. Nice staff decent breakfast "
Bromley View Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (227)
"Terrific hosts! Great accommodations! Best breakfast with local ingredients! Highly recommended 👍"
Harvest Barn Inn
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 RM666
RM733 total
includes taxes & fees
16 Sept - 17 Sept
Colonel Williams 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 RM1,411
RM1,538 total
includes taxes & fees
20 Sept - 21 Sept
Stone Hearth Inn and Eatery
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (106)
"Quaintly decorated. Lisa and Ken were very good hosts. Not a modern high tech property, but very homey and welcoming. "
The price is RM630
RM693 total
includes taxes & fees
9 Sept - 10 Sept
Blue Gentian Lodge at Magic Mountain
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
The price is RM749
RM813 total
includes taxes & fees
9 Sept - 10 Sept
The Carriage Barn Inn
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Vesper
1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (30)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is RM714
RM785 total
includes taxes & fees
9 Sept - 10 Sept
The Vesper
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 RM799
RM871 total
includes taxes & fees
9 Sept - 10 Sept
Windham Hill Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (42)
"Superb stay in all ways!"
The price is RM1,053
RM1,158 total
includes taxes & fees
14 Sept - 15 Sept
Stay At Jimmy's
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 RM842
RM926 total
includes taxes & fees
9 Sept - 10 Sept
The Inn at Ormsby Hill
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. "
Deerfield Valley Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (228)
"Great stay! "
The Jackson
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
Chesterfield Inn
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (252)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is RM894
RM984 total
includes taxes & fees
14 Sept - 15 Sept
The Inn at Manchester
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 RM705
RM776 total
includes taxes & fees
19 Sept - 20 Sept
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.
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Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
Accommodation
34 B&B
Lowest Price
RM630
Highest Price
RM1,865

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 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.
What are the top B&Bs in Chester?
Take a look at this B&B in the surrounding area: Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the city centre. Enjoy the unique decor and fireplace in reception.
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.