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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Chester bed & breakfast

Front of property

1. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (121 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 CA $290
CA $316 total
includes taxes & fees
Aug 12 - Aug 13
Stone Hearth Inn and Eatery
Lounge

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (456 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 CA $107
CA $118 total
includes taxes & fees
Aug 10 - Aug 11
Bromley View Inn
Porch

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (270 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is CA $227
CA $247 total
includes taxes & fees
Aug 23 - Aug 24
Harvest Barn Inn
Kayaking

4. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (121 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is CA $205
CA $225 total
includes taxes & fees
Aug 11 - Aug 12
Blue Gentian Lodge at Magic Mountain
Exterior

5. 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 CA $304
CA $331 total
includes taxes & fees
Aug 17 - Aug 18
Echo Lake Inn
Room, 1 Queen Bed, Garden View | Mountain view

6. 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 CA $260
CA $284 total
includes taxes & fees
Sep 2 - Sep 3
Windham Hill Inn
Front of property

7. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is CA $221
CA $243 total
includes taxes & fees
Aug 9 - Aug 10
Colonel Williams Inn
Free daily continental breakfast

8. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is CA $197
CA $213 total
includes taxes & fees
Aug 19 - Aug 20
The Carriage Barn Inn
Restaurant

9. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (300 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is CA $226
CA $248 total
includes taxes & fees
Aug 9 - Aug 10
The Jackson
Land view from property

10. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (49 reviews)
"Can’t go wrong with this place."
United States
John
The price is CA $208
CA $227 total
includes taxes & fees
Aug 10 - Aug 11
Four Columns Inn
Interior

11. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (70 reviews)
"Great easy parking and seamless entry. Good stay."
United States
Terry
The price is CA $245
CA $270 total
includes taxes & fees
Aug 18 - Aug 19
The Vesper
Property grounds

12. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (362 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is CA $196
CA $247 total
includes taxes & fees
Sep 7 - Sep 8
The Inn at Manchester
Exterior

13. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (128 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is CA $123
CA $174 total
includes taxes & fees
Aug 23 - Aug 24
Deerfield Valley Inn
Front of property

14. 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 CA $336
CA $370 total
includes taxes & fees
Aug 24 - Aug 25
The One Cat B&B
Property grounds

15. Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1 review)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
The price is CA $110
CA $207 total
includes taxes & fees
Aug 9 - Aug 10
Room 7 - family room sleeps 4
Front of property

16. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (50 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is CA $349
CA $384 total
includes taxes & fees
Aug 11 - Aug 12
Stay At Jimmy's
Exterior

17. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is CA $163
CA $267 total
includes taxes & fees
Aug 25 - Aug 26
Sleep Woodstock - Dog Friendly King Suite
Interior

18. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (4 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is CA $314
CA $345 total
includes taxes & fees
Aug 27 - Aug 28
Deer Brook Inn
Garden

19. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (215 reviews)
"Clean and convenient, would stay again. "
United States
Todd
The price is CA $242
CA $266 total
includes taxes & fees
Aug 9 - Aug 10
Big Bears Lodge
Exterior

20. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (59 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is CA $413
CA $454 total
includes taxes & fees
Aug 11 - Aug 12
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.
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Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Giid hotel with several fire pits to sit by the river"
John 1-night trip
Posted 11 hours ago
The Shire Woodstock

Find out more about Chester

Chester B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price

Frequently asked questions

Searching for B&Bs in Chester?
If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide 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 décor. Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your stay in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll be sure to enjoy Chester for its coffeehouses and restaurants. If you're looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like 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 center. Otherwise, look 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, you may want to rent a car for your trip.

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