Bed and Breakfast in Chester

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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Chester bed & breakfast

Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is NZ$393
includes taxes & fees
29 Dec - 30 Dec
Stone Hearth Inn and Eatery
Interior
King & Queen Suite in Historic Inn Circa 1780

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)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is NZ$427
includes taxes & fees
5 Jan - 6 Jan 2026
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!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Chester Depot
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. "
United States
Jacque
The price is NZ$383
includes taxes & fees
4 Jan - 5 Jan 2026
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!

Room in Historic Inn! 20 Minutes to Okemo!
Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is NZ$350
includes taxes & fees
5 Jan - 6 Jan 2026
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

Honeymoon Suite with Jacuzzi Tub in Historic Inn
Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is NZ$386
includes taxes & fees
5 Jan - 6 Jan 2026
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Lounge
Bromley View Inn

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (405)
"Clean and great location with fun lounge area."
United States
Marshall
Bromley View Inn
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (15)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is NZ$224
includes taxes & fees
31 Dec - 1 Jan 2026
The Carriage Barn Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is NZ$269
includes taxes & fees
24 Dec - 25 Dec
Colonel Williams Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (282)
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
United States
Amy
The price is NZ$313
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Manchester
Mountain view
Windham Hill Inn

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$341
includes taxes & fees
5 Jan - 6 Jan 2026
Windham Hill Inn
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is NZ$378
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Ormsby Hill
Kayaking
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
"Lovely pleasant stay. "
United States
Heather
The price is NZ$336
includes taxes & fees
4 Jan - 5 Jan 2026
Blue Gentian Lodge at Magic Mountain
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is NZ$473
includes taxes & fees
4 Jan - 5 Jan 2026
Stay At Jimmy's
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Economy Room
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
"Charming bed and breakfast"
United States
Nicholas
The price is NZ$321
includes taxes & fees
30 Dec - 31 Dec
The Vesper
Exterior
Inn on Putney Road

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is NZ$445
includes taxes & fees
1 Jan - 2 Jan 2026
Inn on Putney Road
Exterior
The One Cat B&B

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is NZ$465
includes taxes & fees
28 Dec - 29 Dec
The One Cat B&B
Garden
Big Bears Lodge

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is NZ$338
includes taxes & fees
1 Jan - 2 Jan 2026
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Comfort and cleanliness. Nice fireplace with comfortable couches. Very nice staff. Pretty Christmas decorations."
Nancy 2-night trip
Posted 4 days ago
Kimpton Taconic Hotel by IHG

Find out more about Chester

Chester B&B information

Number of reviews
2,526
Accommodation
62 B&B
Lowest Price
NZ$224
Highest Price
NZ$473

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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. You might also consider a trip to sites such as Stratton Mountain Resort 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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