Bed and Breakfast in Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured B&B in Chester

Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
The price is NZ$360
includes taxes & fees
9 Dec - 10 Dec
Stone Hearth Inn and Eatery
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
The price is NZ$401
includes taxes & fees
16 Nov - 17 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!

Chester Depot
9.0 out of 10, Wonderful, (2)
"Yes, wonderful location and stay"
United States
Sharon
The price is NZ$287
includes taxes & fees
10 Nov - 11 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!

Chester Depot
9.2 out of 10, Wonderful, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
The price is NZ$269
includes taxes & fees
10 Nov - 11 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

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
The price is NZ$316
includes taxes & fees
9 Nov - 10 Nov
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Lounge
Bromley View Inn

Bromley View Inn

3.5 star property
Bondville
9.0 out of 10, Wonderful, (399)
"Breakfast , beverages and hot tub were nice in addition to the family game room area. "
United States
Lynn
Bromley View Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (243)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Front of property
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (9)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
The price is NZ$306
includes taxes & fees
9 Dec - 10 Dec
Four Columns Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (163)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
The price is NZ$316
includes taxes & fees
7 Dec - 8 Dec
The Carriage Barn Inn
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (147)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is NZ$343
includes taxes & fees
9 Nov - 10 Nov
The Inn at Ormsby Hill
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (241)
"Great stay! "
United States
Romulo
The Jackson
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
The price is NZ$292
includes taxes & fees
20 Nov - 21 Nov
Colonel Williams Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

3.0 star property
West Dover
9.6 out of 10, Exceptional, (83)
"We had a lovely time staying here. "
United States
Jeff
The price is NZ$174
includes taxes & fees
16 Nov - 17 Nov
Deerfield Valley Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

3.5 star property
Manchester
10.0 out of 10, Exceptional, (275)
"The staff was so friendly and helpful. Would definitely recommend. "
United States
Christine
The price is NZ$291
includes taxes & fees
9 Nov - 10 Nov
The Inn at Manchester
Economy Room
The Vesper

The Vesper

3.0 star property
Woodstock
9.0 out of 10, Wonderful, (41)
"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)"
United States
Abigail
The price is NZ$307
includes taxes & fees
13 Nov - 14 Nov
The Vesper
Mountain view
Windham Hill Inn

Windham Hill Inn

4.0 star property
West Townshend
8.6 out of 10, Excellent, (37)
"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. "
United States
Brandon
The price is NZ$347
includes taxes & fees
11 Nov - 12 Nov
Windham Hill Inn
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
The price is NZ$388
includes taxes & fees
11 Nov - 12 Nov
Stay At Jimmy's
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
The price is NZ$478
includes taxes & fees
20 Nov - 21 Nov
The One Cat B&B
Garden
Big Bears Lodge

Big Bears Lodge

3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The property is conveniently located in close proximity to Mt Snow and local restaurants. The staff is friendly. There's a big screen tv room with fireplace and a small sitting room to read or just converse. Rooms are a little dated but clean. Would stay again."
United States
Jonathan
The price is NZ$325
includes taxes & fees
9 Dec - 10 Dec
Big Bears Lodge
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (55)
"Pricey but overall. A wonderful stay. Excellent breakfast, grounds, shower and inn keeper."
United States
Jane
The price is NZ$521
includes taxes & fees
9 Nov - 10 Nov
Inn on Putney Road
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. "
Andrew 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort

Find out more about Chester

Chester B&B information

Number of reviews
2,438
Accommodation
52 B&B
Lowest Price
NZ$174
Highest Price
NZ$521

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: Blue Gentian Lodge at Magic Mountain: 13 rooms. Located 9.8 mi (15.8 km) from the core of Chester. Enjoy the free buffet breakfast and spa.
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.

Explore a world of travel with Expedia