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Featured B&B in Chester

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"Sweet place to stay"
The price is P11,496
P12,531 total
includes taxes & fees
Aug 18 - Aug 19
Stone Hearth Inn and Eatery

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 P10,111
P10,970 total
includes taxes & fees
Sep 2 - Sep 3
The Carriage Barn Inn

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is P17,188
P18,649 total
includes taxes & fees
Aug 25 - Aug 26
Chesterfield Inn

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"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

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 P11,558
P12,714 total
includes taxes & fees
Aug 27 - Aug 28
The One Cat B&B

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 P16,823
P18,506 total
includes taxes & fees
Aug 18 - Aug 19
Inn on Putney Road

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (313)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
The price is P8,990
P9,889 total
includes taxes & fees
Aug 31 - Sep 1
Colonel Williams Inn

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
The price is P11,358
P12,494 total
includes taxes & fees
Aug 24 - Aug 25
Stay At Jimmy's

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (27)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is P9,632
P10,595 total
includes taxes & fees
Aug 20 - Aug 21
The Vesper

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (225)
"Great stay! "
The Jackson

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 P10,788
P11,758 total
includes taxes & fees
Aug 18 - Aug 19
Windham Hill Inn

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
The price is P25,174
P27,692 total
includes taxes & fees
Sep 15 - Sep 16
Woodbridge Inn

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is P11,701
P12,871 total
includes taxes & fees
Aug 19 - Aug 20
Deerhill Inn

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (105)
"Lisa was amazing, super kind and helpful. The rooms were clean and given attention each day. We really enjoyed our stay and will be back next time we are in Vermont. "
The price is P7,934
P8,727 total
includes taxes & fees
Aug 18 - Aug 19
Blue Gentian Lodge at Magic Mountain

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (57)
"I liked that it was right on the scenic route"
Deerfield Valley 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

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.