A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check prices for these dates

Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept
In one month
25 Sept - 27 Sept
In two months
23 Oct - 25 Oct

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 AU$305
includes taxes & fees
15 Sept - 16 Sept
Stone Hearth Inn and Eatery
Lounge

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (470 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is AU$117
includes taxes & fees
1 Sept - 2 Sept
Bromley View Inn
Kayaking

3. 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 AU$228
includes taxes & fees
31 Aug - 1 Sept
Blue Gentian Lodge at Magic Mountain
Porch

4. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (275 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is AU$243
includes taxes & fees
1 Sept - 2 Sept
Harvest Barn Inn
Room, 1 Queen Bed, Garden View | Mountain view

5. 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 AU$283
includes taxes & fees
8 Sept - 9 Sept
Windham Hill Inn
Exterior

6. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (102 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
The price is AU$326
includes taxes & fees
1 Sept - 2 Sept
Echo Lake Inn
Land view from property

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (53 reviews)
"Can’t go wrong with this place."
United States
John
The price is AU$219
includes taxes & fees
2 Sept - 3 Sept
Four Columns Inn
Standard Double Room

8. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is AU$222
includes taxes & fees
4 Sept - 5 Sept
Doveberry Inn
Restaurant

9. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (305 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is AU$274
includes taxes & fees
1 Sept - 2 Sept
The Jackson
Property grounds

10. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (373 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is AU$246
includes taxes & fees
8 Sept - 9 Sept
The Inn at Manchester
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 AU$241
includes taxes & fees
31 Aug - 1 Sept
Colonel Williams Inn
Breakfast area

12. 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 AU$221
includes taxes & fees
30 Aug - 31 Aug
The Carriage Barn Inn
Interior

13. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (74 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is AU$269
includes taxes & fees
31 Aug - 1 Sept
The Vesper
Interior

14. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (6 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is AU$349
includes taxes & fees
31 Aug - 1 Sept
Deer Brook Inn
Exterior

15. 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 AU$173
includes taxes & fees
13 Sept - 14 Sept
Deerfield Valley Inn
Exterior

16. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
The price is AU$232
includes taxes & fees
14 Sept - 15 Sept
Sleep Woodstock - Dog Friendly King Suite
Exterior

17. Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Cute little motel. Place was clean and the host was very helpful with any questions I had. The fire area was nice to go relax at the end of the day. Highly recommended a visit if your in the at area."
United States
Ivy B.
The price is AU$226
includes taxes & fees
2 Sept - 3 Sept
Room 1, peaceful retreat in Manchester - King bed
Garden

18. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (216 reviews)
"Clean and convenient, would stay again. "
United States
Todd
The price is AU$264
includes taxes & fees
28 Aug - 29 Aug
Big Bears Lodge
Front of property

19. 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
30 Aug - 31 Aug
The One Cat B&B
Front of property – evening/night

20. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
The price is AU$758
includes taxes & fees
8 Sept - 9 Sept
Woodbridge 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 and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Would have liked a safe in my room. Rooms were large and clean."
Ruth 3-night trip
Posted 13 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester B&B information

Number of reviews
2,161
Accommodation
66 B&B
Lowest Price
AU$117
Highest Price
AU$758

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 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. 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 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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