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Check prices for these dates

Next weekend
17 July - 19 July
In two weeks
24 July - 26 July
In one month
7 Aug - 9 Aug
In two months
4 Sept - 6 Sept

Our top choices for Chester bed & breakfast

Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is AU$326
includes taxes & fees
20 July - 21 July
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (450 reviews)
"staff actually treated you like family and not another customer & Clean room & relaxing backyard to watch the sunset & great breakfast"
United States
Josh
The price is AU$134
includes taxes & fees
15 July - 16 July
Bromley View Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 reviews)
"Great breakfast!"
United States
Billie
The price is AU$249
includes taxes & fees
14 July - 15 July
Colonel Williams Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (268 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is AU$248
includes taxes & fees
26 July - 27 July
Harvest Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AU$254
includes taxes & fees
20 July - 21 July
The Carriage Barn Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (294 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is AU$255
includes taxes & fees
21 July - 22 July
The Jackson
Kayaking

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (120 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is AU$233
includes taxes & fees
14 July - 15 July
Blue Gentian Lodge at Magic Mountain
Exterior

Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (1 review)
"The room was spotless. The communal guest kitchen is an awesome feature. "
United States
Jacob
The price is AU$215
includes taxes & fees
15 July - 16 July
Room 1, peaceful retreat in Manchester - King bed
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (347 reviews)
"Great cooked to order breakfast, beautiful grounds and perfect central location in town."
United States
Richard
The price is AU$303
includes taxes & fees
20 July - 21 July
The Inn at Manchester
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (46 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AU$332
includes taxes & fees
19 July - 20 July
Four Columns Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (67 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is AU$277
includes taxes & fees
23 July - 24 July
The Vesper
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (125 reviews)
"Very friendly and courteous owner, great location 5 mins away from Mount Snow."
United States
Brandon
The price is AU$191
includes taxes & fees
20 July - 21 July
Deerfield Valley Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AU$384
includes taxes & fees
16 July - 17 July
The One Cat B&B
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is AU$325
includes taxes & fees
14 July - 15 July
Echo Lake Inn
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AU$215
includes taxes & fees
21 July - 22 July
Sleep Woodstock - Dog Friendly King Suite
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is AU$394
includes taxes & fees
14 July - 15 July
Stay At Jimmy's
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (43 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is AU$291
includes taxes & fees
27 July - 28 July
Windham Hill Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (214 reviews)
"Place is great and location as well, 5 minutes from Mount Snow."
United States
Matheus
The price is AU$273
includes taxes & fees
14 July - 15 July
Big Bears Lodge
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
The price is AU$466
includes taxes & fees
14 July - 15 July
Inn on Putney Road
Front of property – evening/night

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (165 reviews)
"This Inn is lovely and our favorite place to stay when we travel to Vermont. The breakfast is amazing!"
United States
Donna
The price is AU$426
includes taxes & fees
14 July - 15 July
The Inn at Ormsby Hill
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The room, including the bathroom, was very clean. The shower was super clean. The breakfast was amazing! The lady who gets the food ready does a phenomenal job."
Pamela 1-night trip
Posted 3 hours ago
Best Western Plus Keene Hotel

Find out more about Chester

Chester B&B information

Number of reviews
2,979
Accommodation
65 B&B
Lowest Price
AU$134
Highest Price
AU$466

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 are some well-liked B&Bs in the area: Stone Hearth Inn and Eatery: 8 rooms. 1.5 mi (2.3 km) from the heart of Chester. Enjoy the free buffet breakfast and unique decor. Bromley View Inn: 16 rooms. Located 17.8 mi (28.6 km) from the core of Chester. 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 Country Store or Lowell Lake State Park 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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