Book Chester Bed & Breakfast

Compare 48 B&B in Chester with updated reviews, rates, and availability.

The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, 190 reviews
"We had an excellent stay! Friendly and helpful check in, beautiful room, and delicious breakfasts. We also enjoyed some time in the bar room. If we are ever in the area again, we would definitely stay here again!"
The price is $165
$182 total
includes taxes & fees
5 Jun - 6 Jun
The Inn at Manchester
The Vesper
3.0 star property
8.0 out of 10, Very Good, 1 review
" Goof"
The price is $177
$195 total
includes taxes & fees
10 Jun - 11 Jun
The Vesper
Stone Hearth Inn and Eatery
2.0 star property
9.2 out of 10, Wonderful, 50 reviews
"My fiance and I had an amazing stay here. Vicki and her staff are incredible and attentive to their guests. The food is beyond amazing one of the best meals we have had. We highly recommend this cute and quaint spot and definitely will be making many trips back! "
The price is $218
$238 total
includes taxes & fees
16 Jun - 17 Jun
Stone Hearth Inn and Eatery
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Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, 171 reviews
"I had a wonderful stay. Kaelan was an awesome host. great breakfast as well!"
The price is $170
$186 total
includes taxes & fees
12 Jun - 13 Jun
Harvest Barn Inn
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, 267 reviews
"The owners are very friendly and hospitable. The property has a lot of history and it's charm makes you feel comfortable and at home. Wonderful stay and would highly recommend!"
The price is $135
$148 total
includes taxes & fees
17 Jun - 18 Jun
Colonel Williams Inn
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, 2 reviews
"Our short but sweet stay was great. Check in was smooth and the breakfast bundles were a nice touch. The rooms are newly designed and felt like such a getaway!"
The price is $249
$274 total
includes taxes & fees
4 Jun - 5 Jun
Stay At Jimmy's
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, 57 reviews
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, 312 reviews
"Its a nice adventure to experience how a new way to accomodate the clients by self-serve from checking in to checking out. The room is clean and comfortable."
Bromley View Inn
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, 167 reviews
"Fantastic homemade breakfast and cookies at night. The rooms were very clean and comfortable. The staff was fantastic! Will be staying again. Book directly and save money."
The price is $263
$289 total
includes taxes & fees
5 Jun - 6 Jun
The Jackson House Inn
Deerfield Valley Inn
3.0 star property
10.0 out of 10, Exceptional, 3 reviews
"I had an absolutely wonderful stay at Dearfield Valley Inn in West Dover, VT. The charming ambiance, attentive staff, and cozy rooms made for a delightful experience. The inn's picturesque surroundings added to the overall charm, creating a perfect getaway. I highly recommend it for anyone seeking a peaceful and memorable stay in Vermont."
The price is $94
$124 total
includes taxes & fees
18 Jun - 19 Jun
Deerfield Valley Inn
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, 200 reviews
"I would 100% stay here again! Incredibly caring, attentive, friendly hosts! We stayed in the Orchid room and it was beautiful. Whether it was remembering a small detail of one guest such as lactose intolerance or recommendations of things to do in town, the owners were always willing to help in any way they can. "
The price is $161
$178 total
includes taxes & fees
6 Jun - 7 Jun
Deerhill Inn
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, 68 reviews
"A wonderful B&B that could use a thorough cleaning. Cute, full of books, great owners and their two cats!"
The price is $198
$218 total
includes taxes & fees
6 Jun - 7 Jun
The One Cat B&B
Windham Hill Resort
3.0 star property
8.2 out of 10, Very Good, 27 reviews
"We stayed in the 8-room converted barn. The room very large and a pleasant surprise featuring a great view, soaking tub in the living area, gas fireplace, and a very comfortable king bed. I would give Windham Hill Inn five stars, but I deducted a star because of a clogged bathroom sink, a difficult to control HVAC system, and live and dead bugs in the room. Although somewhat dated, the room was spectacular for the price. "
The price is $173
$188 total
includes taxes & fees
4 Jun - 5 Jun
Windham Hill Resort
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, 123 reviews
"Great nights stay and very walkable to the center of town. The host Joe was awesome!"
The price is $225
$244 total
includes taxes & fees
4 Jun - 5 Jun
The Carriage Barn Inn
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, 90 reviews
"Lovely inn. Went to VT to see the total eclipse "
The price is $191
$209 total
includes taxes & fees
18 Jun - 19 Jun
Echo Lake Inn
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, 39 reviews
"The Inn is charming and beautifully furnished. The gardens are beautiful. The innkeeper and staff were gracious and our room was decked out with complimentary Vermont treats. The breakfast was lavish - muffins, fruit, eggs, potatoes, sausage, freshly ground coffee and fresh-squeezed juice. We only did a quick overnight visit but next time it would be fun to stay longer to take advantage of the game room and the many books."
The price is $268
$295 total
includes taxes & fees
16 Jun - 17 Jun
Inn on Putney Road
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, 106 reviews
"Great breakfast; grounds were beautiful; great innkeepers! Would recommend to others"
The price is $289
$318 total
includes taxes & fees
12 Jun - 13 Jun
The Inn at Ormsby Hill
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, 50 reviews
"it was the most charming, cleanest, best breakfast we've ever had going to b&bs 6-12 times a year for over 20 years. it looked like the kind you see in magazines but never in real life."
The Buckmaster Inn
Golden Stage Inn B&B
3.5 star property
10.0 out of 10, Exceptional, 22 reviews
"We chose this bed and breakfast based on others’ reviews- and you should, too! Our room was lovely and homey and had everything you’d want or need available. Mike and Julie are spectacularly thoughtful hosts. We felt welcomed, cared for, and a little bit spoiled :) during our three day stay. Will absolutely stay here again on our next visit to VT! "
Golden Stage Inn B&B
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, 100 reviews
"A true find!"
The price is $301
$327 total
includes taxes & fees
6 Jun - 7 Jun
Chesterfield Inn
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See all available properties in Chester
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.

Other property types in Chester

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, 30 reviews
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 32 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, 69 reviews
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is $317
$384 total
includes taxes & fees
12 Jun - 13 Jun
Long Trail House at Stratton Mountain Resort
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.

Chester B&B information

Number of reviews
1,832
Accommodation
48 B&B
Lowest Price
CNY684
Highest Price
CNY2,181

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?
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 décor. King & Queen Suite in Historic Inn Circa 1780: 0.3 mi (0.4 km) from the downtown core. Honeymoon Suite with Jacuzzi Tub in Historic Inn: Situated 0.3 mi (0.4 km) from the heart of Chester. Room in Historic Inn! 20 Minutes to Okemo!: 0.3 mi (0.4 km) from the heart of downtown.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 7 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 Baltimore Covered Bridge 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.

Recent reviews of Chester hotels
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