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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 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, (126 reviews)
"Wonderful staff and restaurant"
United States
John
The price is AED 714
AED 778 total
includes taxes & fees
24 Sep - 25 Sep
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 AED 584
AED 642 total
includes taxes & fees
24 Sep - 25 Sep
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 AED 686
AED 748 total
includes taxes & fees
24 Sep - 25 Sep
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, (46 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
20 Oct - 21 Oct
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 AED 546
AED 596 total
includes taxes & fees
29 Sep - 30 Sep
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 AED 1,181
AED 1,287 total
includes taxes & fees
13 Oct - 14 Oct
Echo Lake 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 AED 567
AED 624 total
includes taxes & fees
29 Sep - 30 Sep
Colonel Williams Inn
Standard Double Room | WiFi (free)

8. 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 AED 510
AED 561 total
includes taxes & fees
19 Oct - 20 Oct
Doveberry Inn
Exterior

9. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 reviews)
The price is AED 363
AED 501 total
includes taxes & fees
24 Sep - 25 Sep
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, (382 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is AED 1,008
AED 1,275 total
includes taxes & fees
28 Sep - 29 Sep
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 AED 561
AED 609 total
includes taxes & fees
24 Sep - 25 Sep
The Carriage Barn Inn
Garden

12. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (217 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is AED 634
AED 697 total
includes taxes & fees
24 Sep - 25 Sep
Big Bears Lodge
Property grounds

13. Room 4 - Prickly Pear double room

Room 4 - Prickly Pear double room
Manchester
10.0 out of 10, Exceptional, (1 review)
"Awesome place to stay - loved it!"
United States
Kristin J.
The price is AED 289
AED 543 total
includes taxes & fees
29 Sep - 30 Sep
Room 4 - Prickly Pear double room
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 AED 1,818
AED 2,000 total
includes taxes & fees
27 Sep - 28 Sep
Woodbridge Inn
Exterior

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 378
AED 611 total
includes taxes & fees
27 Sep - 28 Sep
Sleep Woodstock - 2 Double Beds - Dog Friendly
Restaurant

16. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (322 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 AED 1,319
AED 1,451 total
includes taxes & fees
24 Sep - 25 Sep
The Jackson
Front of property - evening/night

17. 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 AED 1,319
AED 1,450 total
includes taxes & fees
27 Sep - 28 Sep
The Inn at Ormsby Hill
Property entrance

18. 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 1,102
AED 1,212 total
includes taxes & fees
27 Sep - 28 Sep
The One Cat B&B
Interior

19. 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 AED 1,566
AED 1,723 total
includes taxes & fees
20 Oct - 21 Oct
Deer Brook Inn
Interior

20. 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 AED 1,263
AED 1,389 total
includes taxes & fees
21 Oct - 22 Oct
The Vesper
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 Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 3 hours ago
The Equinox Golf Resort And Spa

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.
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.