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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 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 AED 767
AED 836 total
includes taxes & fees
10 Aug - 11 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, (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 AED 281
AED 309 total
includes taxes & fees
10 Aug - 11 Aug
Bromley View Inn
Porch

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (271 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is AED 620
AED 675 total
includes taxes & fees
16 Aug - 17 Aug
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 AED 523
AED 575 total
includes taxes & fees
16 Aug - 17 Aug
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 AED 821
AED 895 total
includes taxes & fees
10 Aug - 11 Aug
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 AED 683
AED 744 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 579
AED 636 total
includes taxes & fees
12 Aug - 13 Aug
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 AED 537
AED 582 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 592
AED 651 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 564
AED 614 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 643
AED 707 total
includes taxes & fees
18 Aug - 19 Aug
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, (364 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is AED 512
AED 648 total
includes taxes & fees
7 Sep - 8 Sep
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 AED 323
AED 456 total
includes taxes & fees
23 Aug - 24 Aug
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 AED 886
AED 975 total
includes taxes & fees
10 Aug - 11 Aug
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 AED 289
AED 543 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 915
AED 1,006 total
includes taxes & fees
11 Aug - 12 Aug
Stay At Jimmy's
Exterior

17. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 428
AED 704 total
includes taxes & fees
25 Aug - 26 Aug
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 AED 846
AED 931 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 634
AED 697 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 1,083
AED 1,191 total
includes taxes & fees
10 Aug - 11 Aug
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Clean, comfortable, great location, friendly staff"
william 1-night trip
Posted 2 hours ago
Hampton Inn and Suites Manchester

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.