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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

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, (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie was so welcoming and kind. We can’t say enough good things! Highly recommend"
United States
Kathleen
The price is Rp3.657.715
Rp3.986.909 total
includes taxes & fees
14 Sept - 15 Sept
Stone Hearth Inn and Eatery
Porch

2. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (279 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is Rp3.178.201
Rp3.464.239 total
includes taxes & fees
14 Sept - 15 Sept
Harvest Barn 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 Rp2.609.139
Rp2.870.052 total
includes taxes & fees
15 Sept - 16 Sept
Blue Gentian Lodge at Magic Mountain
Exterior

4. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (101 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
The price is Rp4.036.110
Rp4.399.360 total
includes taxes & fees
14 Sept - 15 Sept
Echo Lake Inn
Land view from property

5. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is Rp2.747.860
Rp2.995.167 total
includes taxes & fees
13 Sept - 14 Sept
Four Columns 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, (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 Rp4.192.856
Rp4.570.292 total
includes taxes & fees
23 Sept - 24 Sept
Windham Hill Inn
Front of property

7. 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 Rp2.757.983
Rp3.033.956 total
includes taxes & fees
22 Sept - 23 Sept
Colonel Williams Inn
Standard Double Room | Free WiFi

8. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
"Great location… very clean"
United States
Veronica
The price is Rp2.647.663
Rp2.912.429 total
includes taxes & fees
12 Sept - 13 Sept
Doveberry Inn
Restaurant

9. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (314 reviews)
"Love this B&B - very well located, the food is amazing and the bedrooms are very comfy! Highly recommend!"
United States
Yanil
The price is Rp4.386.750
Rp4.825.425 total
includes taxes & fees
13 Sept - 14 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, (377 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is Rp3.703.577
Rp4.685.418 total
includes taxes & fees
21 Sept - 22 Sept
The Inn at Manchester
Free daily continental breakfast

11. 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 Rp2.757.211
Rp2.991.574 total
includes taxes & fees
13 Sept - 14 Sept
The Carriage Barn Inn
Interior

12. 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 Rp4.073.935
Rp4.481.328 total
includes taxes & fees
13 Sept - 14 Sept
Deer Brook Inn
Garden

13. 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 Rp3.020.648
Rp3.322.887 total
includes taxes & fees
23 Sept - 24 Sept
Big Bears Lodge
Interior

14. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (77 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is Rp4.386.733
Rp4.825.406 total
includes taxes & fees
14 Sept - 15 Sept
The Vesper
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 Rp1.539.567
Rp2.175.076 total
includes taxes & fees
28 Sept - 29 Sept
Deerfield Valley Inn
Front of property

16. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (52 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
The price is Rp5.246.553
Rp5.771.209 total
includes taxes & fees
15 Sept - 16 Sept
Stay At Jimmy's
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 Rp5.253.300
Rp5.778.630 total
includes taxes & fees
19 Sept - 20 Sept
The One Cat B&B
Front of property – evening/night

18. 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 Rp8.667.945
Rp9.534.740 total
includes taxes & fees
15 Sept - 16 Sept
Woodbridge 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 Rp6.299.373
Rp6.929.311 total
includes taxes & fees
15 Sept - 16 Sept
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

On The River Inn

On The River Inn

8/10 Good
"We selected and reserved a room with a river view and were assigned 105. The actual river was not visible from our windows or balcony. That was a little disappointing. The room itself was very nice and well maintained. The food in the 506 Bistro was excellent, both the daily breakfasts and the two dinners we had there. The wings with maple were especially tasty. The staff we engaged were nice. We probably will not visit Woodstock again now that we spent a few days there, but if we did I would stay there again but not pay a premium price for a river view."
Russell 5-night trip
Posted 9 hours ago
On The River Inn

Find out more about Chester

Chester B&B information

Number of reviews
2,566
Accommodation
35 B&B
Lowest Price
Rp2.175.076
Highest Price
Rp9.534.740

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 surrounding 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. Situated 17.8 mi (28.6 km) from the heart of Chester. 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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