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Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sep - 13 Sep
In two months
9 Oct - 11 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, (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 5.464.535 ₫
5.956.343 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Stone Hearth Inn and Eatery
Lounge

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (458 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 2.003.634 ₫
2.203.840 ₫ total
includes taxes & fees
16 Aug - 17 Aug
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, (122 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is 3.897.989 ₫
4.287.788 ₫ total
includes taxes & fees
23 Aug - 24 Aug
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, (273 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is 4.548.874 ₫
4.958.273 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Harvest Barn Inn
Land view from property

5. 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 4.103.703 ₫
4.473.036 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Four Columns Inn
Exterior

6. 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 6.029.849 ₫
6.572.536 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Echo Lake Inn
Room, 1 Queen Bed, Garden View | Mountain view

7. 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 4.862.022 ₫
5.299.604 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Windham Hill Inn
Restaurant

8. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (301 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is 4.214.537 ₫
4.635.991 ₫ total
includes taxes & fees
12 Aug - 13 Aug
The Jackson
Front of property

9. 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 4.120.358 ₫
4.532.655 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Colonel Williams Inn
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, (364 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is 3.649.460 ₫
4.616.894 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Inn at Manchester
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 4.578.175 ₫
5.035.993 ₫ total
includes taxes & fees
10 Sept - 11 Sept
The Vesper
Free daily continental breakfast

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 3.822.854 ₫
4.147.797 ₫ total
includes taxes & fees
13 Aug - 14 Aug
The Carriage Barn Inn
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 2.300.076 ₫
3.249.511 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Deerfield Valley Inn
Interior

14. 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 6.086.357 ₫
6.694.992 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Deer Brook Inn
Front of property

15. 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 6.514.089 ₫
7.165.498 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Stay At Jimmy's
Garden

16. 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 4.512.773 ₫
4.964.312 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Big Bears Lodge
Front of property

17. 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 6.540.250 ₫
7.194.274 ₫ total
includes taxes & fees
25 Aug - 26 Aug
The One Cat B&B
Front of property – evening/night

18. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (171 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is 7.049.145 ₫
7.754.059 ₫ total
includes taxes & fees
18 Aug - 19 Aug
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast was great. The staff was very friendly."
Greg 2-night trip
Posted 4 hours ago
Hampton Inn Brattleboro

Find out more about Chester

Chester B&B information

Number of reviews
2,960
Accommodation
35 B&B
Lowest Price
2.203.840 ₫
Highest Price
7.754.059 ₫

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.
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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