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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

B&B in Chester

Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (369)
"After working an entire weekend with festivities in the area checking into here for some much needed rest was the best decision we made very comfortable very nice and very clean "
Bromley View Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (223)
"A quaint boutique historic hotel with a cool little bar and fine dining. The view from our room overlooking the garden and lush lawn added to the tranquil atmosphere that we were hoping for. The owners were pleasant and friendly. "
The Jackson
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (250)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
The price is AED 545
AED 600 total
includes taxes & fees
1 Sep - 2 Sep
The Inn at Manchester
The Inn at Ormsby Hill
Front of property

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (130)
"beautiful grounds, plentiful outdoor seating, excellent breakfasts"
The price is AED 729
AED 802 total
includes taxes & fees
4 Aug - 5 Aug
The Inn at Ormsby Hill
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (38)
"Superb stay in all ways!"
The price is AED 915
AED 1,006 total
includes taxes & fees
7 Aug - 8 Aug
Stay At Jimmy's
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is AED 515
AED 561 total
includes taxes & fees
18 Aug - 19 Aug
Colonel Williams Inn
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (26)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is AED 659
AED 725 total
includes taxes & fees
10 Aug - 11 Aug
The Vesper
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is AED 631
AED 685 total
includes taxes & fees
2 Sep - 3 Sep
The Carriage Barn Inn
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (103)
"The most comfortable stay I have had in a long time. I look forward to visiting the Blue Gentian Lodge again!"
The price is AED 485
AED 534 total
includes taxes & fees
4 Aug - 5 Aug
Blue Gentian Lodge at Magic Mountain
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (222)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
Harvest Barn Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is AED 740
AED 806 total
includes taxes & fees
5 Aug - 6 Aug
Stone Hearth Inn and Eatery
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is AED 1,083
AED 1,191 total
includes taxes & fees
4 Aug - 5 Aug
Inn on Putney Road
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (54)
"I liked that it was right on the scenic route"
Deerfield Valley Inn
Windham Hill Inn
Mountain view

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is AED 694
AED 757 total
includes taxes & fees
4 Aug - 5 Aug
Windham Hill Inn
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is AED 1,106
AED 1,200 total
includes taxes & fees
4 Aug - 5 Aug
Chesterfield Inn
Big Bears Lodge
Garden

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (179)
"So close to Mount snow it’s a great place to stay "
The price is AED 612
AED 674 total
includes taxes & fees
4 Aug - 5 Aug
Big Bears Lodge
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is AED 684
AED 753 total
includes taxes & fees
6 Aug - 7 Aug
The One Cat B&B
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
Woodbridge Inn
Echo Lake Inn
Outdoor pool

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is AED 753
AED 821 total
includes taxes & fees
11 Aug - 12 Aug
Echo Lake Inn
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 Putney Inn

The Putney Inn

10/10 Excellent
"Clean and neat. Friendly service. Just what I needed"
Matthew 1-night trip
Posted 1 day ago
The Putney Inn

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?
Check out this B&B in the surrounding area: Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the downtown core. 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 Plummer's Sugar House 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.