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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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, (125 reviews)
"Wonderful staff and restaurant"
United States
John
The price is NT$6,647
NT$7,246 total
includes taxes & fees
Sep 22 - Sep 23
Stone Hearth Inn and Eatery
Kayaking

2. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (124 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is NT$5,060
NT$5,566 total
includes taxes & fees
Sep 23 - Sep 24
Blue Gentian Lodge at Magic Mountain
Porch

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (282 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is NT$6,126
NT$6,678 total
includes taxes & fees
Sep 22 - Sep 23
Harvest Barn Inn
Room, 1 Queen Bed, Garden View | Mountain view

4. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (45 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 NT$5,914
NT$6,447 total
includes taxes & fees
Oct 20 - Oct 21
Windham Hill Inn
Land view from property

5. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (55 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is NT$4,984
NT$5,432 total
includes taxes & fees
Sep 22 - Sep 23
Four Columns Inn
Exterior

6. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (103 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
The price is NT$10,440
NT$11,379 total
includes taxes & fees
Oct 13 - Oct 14
Echo Lake Inn
Standard Double Room | WiFi (free)

7. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is NT$4,654
NT$5,120 total
includes taxes & fees
Oct 19 - Oct 20
Doveberry Inn
Front of property

8. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (359 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 NT$5,012
NT$5,514 total
includes taxes & fees
Sep 22 - Sep 23
Colonel Williams Inn
Exterior

9. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 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 NT$3,023
NT$4,201 total
includes taxes & fees
Sep 22 - Sep 23
Deerfield Valley 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, (381 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is NT$6,731
NT$8,515 total
includes taxes & fees
Sep 23 - Sep 24
The Inn at Manchester
Restaurant

11. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (320 reviews)
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
United States
Laura
The price is NT$10,343
NT$11,377 total
includes taxes & fees
Sep 22 - Sep 23
The Jackson
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 NT$5,011
NT$5,437 total
includes taxes & fees
Sep 22 - Sep 23
The Carriage Barn Inn
Garden

13. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (217 reviews)
"Clean and convenient, would stay again. "
United States
Todd
The price is NT$5,490
NT$6,039 total
includes taxes & fees
Sep 22 - Sep 23
Big Bears Lodge
Front of property - evening/night

14. 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 NT$15,753
NT$17,328 total
includes taxes & fees
Sep 22 - Sep 23
Woodbridge Inn
Interior

15. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (78 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is NT$8,951
NT$9,846 total
includes taxes & fees
Sep 22 - Sep 23
The Vesper
Interior

16. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is NT$13,705
NT$15,076 total
includes taxes & fees
Sep 27 - Sep 28
Deer Brook Inn
Property entrance

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 NT$9,547
NT$10,502 total
includes taxes & fees
Sep 24 - Sep 25
The One Cat B&B
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 NT$9,583
NT$10,398 total
includes taxes & fees
Oct 18 - Oct 19
Chesterfield Inn
Front of property - evening/night

19. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is NT$11,425
NT$12,567 total
includes taxes & fees
Sep 22 - Sep 23
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

The Manchester View

The Manchester View

10/10 Excellent
"Our suite was spotless, beautiful rooms with fireplace, it was beautifully decorated! Breakfast was good, couldn’t ask for anymore!!!!!"
Donna 2-night trip
Posted 17 hours ago
The Manchester View

Find out more about Chester

Chester B&B information

Number of reviews
2,401
Accommodation
35 B&B
Lowest Price
NT$4,201
Highest Price
NT$17,328

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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 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. Situated 17.8 mi (28.6 km) from the heart of Chester. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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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