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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured B&B in Chester and around

Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (101)
"Good breakfast and dinner options. Great location for hiking."
The price is €266
includes taxes & fees
15 Oct - 16 Oct
Stone Hearth Inn and Eatery
Interior
King & Queen Suite in Historic Inn Circa 1780
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 €202
includes taxes & fees
4 Nov - 5 Nov
King & Queen Suite in Historic Inn Circa 1780
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
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 €143
includes taxes & fees
2 Nov - 3 Nov
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!
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 €148
includes taxes & fees
2 Nov - 3 Nov
Room in Historic Inn! 20 Minutes to Okemo!
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn
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 €214
includes taxes & fees
15 Oct - 16 Oct
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Lounge
Bromley View Inn
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (391)
"Great place and close to everything "
Bromley View Inn
Porch
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (238)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
Harvest Barn Inn
Dining
Four Columns Inn
Four Columns Inn
3.0 star property
9.6 out of 10, Exceptional, (7)
"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
Front of property
The Jackson
The Jackson
4.0 star property
9.8 out of 10, Exceptional, (237)
"Excellent Vintage style B&B. "
The Jackson
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (332)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
The price is €150
includes taxes & fees
22 Oct - 23 Oct
Colonel Williams Inn
Kayaking
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
2.5 star property
9.2 out of 10, Wonderful, (110)
"Lovely pleasant stay. "
The price is €170
includes taxes & fees
19 Oct - 20 Oct
Blue Gentian Lodge at Magic Mountain
Property grounds
The Inn at Manchester
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (267)
"Friendly staff and very nice breakfast. "
The price is €141
includes taxes & fees
2 Nov - 3 Nov
The Inn at Manchester
Front of property
The Inn at Ormsby Hill
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (142)
"Lovely place to stay Jack and Maryann excellent hosts"
The price is €169
includes taxes & fees
2 Nov - 3 Nov
The Inn at Ormsby Hill
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (158)
"Great BB. Very charming and cozy! Will definitely stay again! "
The price is €177
includes taxes & fees
26 Oct - 27 Oct
The Carriage Barn Inn
Exterior
The One Cat B&B
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 €238
includes taxes & fees
5 Nov - 6 Nov
The One Cat B&B
Exterior
Deerfield Valley Inn
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (69)
"We had a lovely time staying here. "
Deerfield Valley Inn
Mountain view
Windham Hill Inn
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 €178
includes taxes & fees
21 Oct - 22 Oct
Windham Hill Inn
Garden
Big Bears Lodge
Big Bears Lodge
3.0 star property
9.0 out of 10, Wonderful, (182)
"So close to Mount snow it’s a great place to stay "
The price is €158
includes taxes & fees
27 Oct - 28 Oct
Big Bears Lodge
Front of property
Stay At Jimmy's
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 €237
includes taxes & fees
3 Nov - 4 Nov
Stay At Jimmy's
Economy Room
The Vesper
The Vesper
3.0 star property
9.2 out of 10, Wonderful, (37)
"Adorable home and room. Very clean. Great location. Loved our stay! "
The price is €177
includes taxes & fees
28 Oct - 29 Oct
The Vesper
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

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Front desk staff went above and beyond to help when I made a mistake on the date of reservation. They found us a room even though they were mostly full. Room was clean and comfortable. Breakfast the next day was excellent and our server was personable and friendly."
Sheila 1-night trip
Posted 2 days ago
Jackson Gore Village

Find out more about Chester

Chester B&B information

Number of reviews
2,417
Accommodation
52 B&B
Lowest Price
€141
Highest Price
€266

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?
Here is a B&B that guests like in the surrounding area: Harvest Barn Inn: 7 rooms. Located 10.4 mi (16.8 km) from the core of Chester. Enjoy the free full breakfast and patio area.
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 Grafton Historical Society 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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