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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 AU$337
includes taxes & fees
25 Aug - 26 Aug
Stone Hearth Inn and Eatery

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is AU$327
includes taxes & fees
19 Aug - 20 Aug
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (15)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is AU$353
includes taxes & fees
19 Aug - 20 Aug
King & Queen Suite in Historic Inn Circa 1780

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
The price is AU$242
includes taxes & fees
26 Aug - 27 Aug
Room in Historic Inn! 20 Minutes to Okemo!

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is AU$260
includes taxes & fees
1 Sept - 2 Sept
Honeymoon Suite with Jacuzzi Tub in Historic Inn

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 AU$292
includes taxes & fees
4 Sept - 5 Sept
The Carriage Barn Inn

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is AU$502
includes taxes & fees
25 Aug - 26 Aug
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 AU$342
includes taxes & fees
27 Aug - 28 Aug
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 AU$498
includes taxes & fees
26 Aug - 27 Aug
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 AU$264
includes taxes & fees
1 Sept - 2 Sept
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 AU$336
includes taxes & fees
25 Aug - 26 Aug
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 AU$285
includes taxes & fees
20 Aug - 21 Aug
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 AU$313
includes taxes & fees
8 Sept - 9 Sept
Windham Hill Inn

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
The price is AU$746
includes taxes & fees
15 Sept - 16 Sept
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 AU$340
includes taxes & fees
19 Aug - 20 Aug
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 AU$230
includes taxes & fees
19 Aug - 20 Aug
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 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?
Take a look at this B&B in the surrounding area: Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the city centre. 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 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 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.