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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

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, (122 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is P12,842
P13,998 total
includes taxes & fees
Aug 25 - Aug 26
Stone Hearth Inn and Eatery
WiFi (free)

2. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is P9,296
P10,225 total
includes taxes & fees
Aug 22 - Aug 23
Doveberry Inn
Porch

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (274 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is P10,744
P11,711 total
includes taxes & fees
Aug 31 - Sep 1
Harvest Barn Inn
Lounge

4. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (464 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is P4,701
P5,170 total
includes taxes & fees
Aug 20 - Aug 21
Bromley View Inn
Kayaking

5. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (123 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is P9,161
P10,077 total
includes taxes & fees
Aug 26 - Aug 27
Blue Gentian Lodge at Magic Mountain
Land view from property

6. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (51 reviews)
"Can’t go wrong with this place."
United States
John
The price is P9,628
P10,494 total
includes taxes & fees
Aug 25 - Aug 26
Four Columns Inn
Exterior

7. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (101 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 P14,171
P15,446 total
includes taxes & fees
Sep 16 - Sep 17
Echo Lake Inn
Mountain view

8. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (44 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 P11,483
P12,517 total
includes taxes & fees
Aug 31 - Sep 1
Windham Hill Inn
Free daily continental breakfast

9. 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 P8,984
P9,748 total
includes taxes & fees
Aug 31 - Sep 1
The Carriage Barn Inn
Restaurant

10. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (303 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is P9,904
P10,895 total
includes taxes & fees
Aug 25 - Aug 26
The Jackson
Front of property

11. 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 P9,683
P10,652 total
includes taxes & fees
Aug 31 - Sep 1
Colonel Williams Inn
Interior

12. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (73 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is P10,759
P11,835 total
includes taxes & fees
Aug 31 - Sep 1
The Vesper
Property grounds

13. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (369 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is P8,576
P10,850 total
includes taxes & fees
Sep 9 - Sep 10
The Inn at Manchester
Exterior

14. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (132 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 P5,405
P7,637 total
includes taxes & fees
Sep 7 - Sep 8
Deerfield Valley Inn
Front of property

15. 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 P15,370
P16,907 total
includes taxes & fees
Aug 31 - Sep 1
The One Cat B&B
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 P15,385
P16,924 total
includes taxes & fees
Aug 23 - Aug 24
Stay At Jimmy's
Garden

17. 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 P10,605
P11,666 total
includes taxes & fees
Aug 29 - Aug 30
Big Bears Lodge
Front of property - evening/night

18. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is P18,607
P20,189 total
includes taxes & fees
Aug 20 - Aug 21
Chesterfield Inn
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The facility was clean, comfortable and friendly staff"
William 1-night trip
Posted 3 hours ago
Hampton Inn Brattleboro

Find out more about Chester

Chester B&B information

Number of reviews
2,991
Accommodation
35 B&B
Lowest Price
P5,170
Highest Price
P20,189

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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