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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Featured B&B in Chester

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 AU$460
includes taxes & fees
21 Oct - 22 Oct
Stone Hearth Inn and Eatery
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Dining

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is AU$248
includes taxes & fees
2 Nov - 3 Nov
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is AU$370
includes taxes & fees
9 Oct - 10 Oct
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
The price is AU$255
includes taxes & fees
2 Nov - 3 Nov
Room in Historic Inn! 20 Minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.8 out of 10, Exceptional, (16)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is AU$520
includes taxes & fees
9 Oct - 10 Oct
King & Queen Suite in Historic Inn Circa 1780
Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (390)
"Older ski mountain motel, kind of a homey feeling. Our stay was very quiet and comfortable. Would stay again"
Bromley View Inn
Four Columns Inn
Dining

Four Columns Inn

3.0 star property
9.2 out of 10, Wonderful, (5)
"So much charm! This place was absolutely outstanding. Already trying to figure out how we can come back for a longer stay."
Four Columns Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (237)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
Harvest Barn Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (330)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is AU$238
includes taxes & fees
21 Oct - 22 Oct
Colonel Williams Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (236)
"Excellent Vintage style B&B. "
The Jackson
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (110)
"Lovely pleasant stay. "
The price is AU$290
includes taxes & fees
13 Oct - 14 Oct
Blue Gentian Lodge at Magic Mountain
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (265)
"Friendly staff and very nice breakfast. "
The price is AU$248
includes taxes & fees
2 Nov - 3 Nov
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, (141)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is AU$290
includes taxes & fees
2 Nov - 3 Nov
The Inn at Ormsby Hill
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (157)
"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 AU$308
includes taxes & fees
16 Oct - 17 Oct
The Carriage Barn Inn
The Vesper
Economy Room

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (34)
"Adorable home and room. Very clean. Great location. Loved our stay! "
The price is AU$293
includes taxes & fees
3 Nov - 4 Nov
The Vesper
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (44)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is AU$416
includes taxes & fees
3 Nov - 4 Nov
Stay At Jimmy's
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (55)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
The price is AU$446
includes taxes & fees
2 Nov - 3 Nov
Inn on Putney Road
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 AU$300
includes taxes & fees
22 Oct - 23 Oct
Windham Hill Inn
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 AU$277
includes taxes & fees
13 Oct - 14 Oct
Big Bears Lodge
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 AU$409
includes taxes & fees
6 Nov - 7 Nov
The One Cat 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.
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Top Chester Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Very nice property. Would love to visit again."
Harvey 2-night trip
Posted 1 day ago
Woodstock Inn & Resort

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
2,377
Accommodation
52 B&B
Lowest Price
AU$238
Highest Price
AU$520

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?
Although there aren't any B&Bs in town, you might be interested in one of these choices if you're hoping to find a place to stay where breakfast is included in your stay: Fullerton Inn Stone Hearth Inn and Eatery Motel in the Meadow
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.

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