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Browse Select Chester B&B

The Inn at Manchester
Property grounds
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (192)
"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 ₹14,639
₹16,102 total
includes taxes & fees
7 Jul - 8 Jul
The Inn at Manchester
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper
3.0 star property
9.6 out of 10, Exceptional, (4)
"The Vesper is just the right amount of historic charm mixed with a clean, modern aesthetic. Breakfast was very tasty and made better by causal conversation with other guests. The sound machine in the room and hiking suggestions were a really nice touch! 10 out of 10 would stay here again (but longer next time!)."
The price is ₹14,394
₹15,833 total
includes taxes & fees
2 Jul - 3 Jul
The Vesper
Bromley View Inn
Lounge
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (312)
"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
Stone Hearth Inn and Eatery
Front of property
Stone Hearth Inn and Eatery
2.0 star property
9.2 out of 10, Wonderful, (53)
"Excellent would recommend to family and friends"
The price is ₹19,499
₹21,253 total
includes taxes & fees
23 Jun - 24 Jun
Stone Hearth Inn and Eatery
Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (268)
"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 ₹11,515
₹12,552 total
includes taxes & fees
9 Jul - 10 Jul
Colonel Williams Inn
Stay At Jimmy's
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (3)
"Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful (...
The price is ₹20,829
₹22,911 total
includes taxes & fees
25 Jun - 26 Jun
Stay At Jimmy's
The Inn at Ormsby Hill
View from property
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (106)
"Property is stunning. Inn keepers are delightful and helpful. Room is clean, cozy, and bed is comfortable. Breakfast is delicious. "
The price is ₹24,454
₹26,900 total
includes taxes & fees
24 Jun - 25 Jun
The Inn at Ormsby Hill
Harvest Barn Inn
Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (171)
"I had a wonderful stay. Kaelan was an awesome host. great breakfast as well!"
The price is ₹14,237
₹15,518 total
includes taxes & fees
27 Jun - 28 Jun
Harvest Barn Inn
Woodbridge Inn
Front of property – evening/night
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, (57)
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Deerfield Valley Inn
Exterior
Deerfield Valley Inn
3.0 star property
10.0 out of 10, Exceptional, (3)
"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 ₹8,293
₹10,795 total
includes taxes & fees
23 Jun - 24 Jun
Deerfield Valley Inn
The Carriage Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (126)
"Charming old inn. We enjoyed our stay very much!"
The price is ₹17,797
₹19,310 total
includes taxes & fees
25 Jun - 26 Jun
The Carriage Barn Inn
The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (70)
"Perfect location near downtown Brattleboro. Convenient, easy walk to shops, restaurants, museums. Pat and Conrad were warm, welcoming hosts. Conrad's homemade bread was delicious. I'm returning in October for his homemade English muffins and for some leaf peeping in the Green Mountains and the White Mountains just across the river. My room was very comfortable, with a comfy loveseat tucked under the corner windows for a perfect reading nook and what was probably the most comfortable bed I've...
The price is ₹16,691
₹18,360 total
includes taxes & fees
9 Jul - 10 Jul
The One Cat B&B
The Buckmaster Inn
Exterior
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (50)
"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
The Jackson House Inn
Fireplace
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (167)
"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 ₹23,776
₹26,154 total
includes taxes & fees
23 Jun - 24 Jun
The Jackson House Inn
Big Bears Lodge
Outdoor spa tub
Big Bears Lodge
3.0 star property
8.8 out of 10, Excellent, (150)
"Staff very accommodating! Loved the place."
The price is ₹13,467
₹14,814 total
includes taxes & fees
22 Jun - 23 Jun
Big Bears Lodge
Windham Hill Resort
Romantic Room, 1 King Bed | Mountain view
Windham Hill Resort
3.0 star property
8.2 out of 10, Very good, (28)
"Amazing trip. Beautiful property. Hope to return someday. "
The price is ₹13,637
₹14,864 total
includes taxes & fees
23 Jun - 24 Jun
Windham Hill Resort
Echo Lake Inn
Exterior
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (91)
"Staff were great. Bathroom tiny. No help carrying bags up steep stairs. Breakfast very good."
The price is ₹16,851
₹18,368 total
includes taxes & fees
22 Jul - 23 Jul
Echo Lake Inn
Inn on Putney Road
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (40)
"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 ₹24,597
₹27,057 total
includes taxes & fees
25 Jun - 26 Jun
Inn on Putney Road
Deerhill Inn
Exterior
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, (200)
"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 ₹13,833
₹15,217 total
includes taxes & fees
23 Jun - 24 Jun
Deerhill Inn
Golden Stage Inn B&B
Seasonal outdoor pool
Golden Stage Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (22)
"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
Don't see what you're looking for?
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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (70)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is ₹25,912
₹31,354 total
includes taxes & fees
25 Jun - 26 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
Accommodation
 B&B
Lowest Price
Highest Price

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.
How many bed & breakfasts should I expect to find in Chester?
Expedia has 7 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 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 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.

Chester Hotel Reviews
Expedia verified reviews

The Covered Bridge Inn

The Covered Bridge Inn

5/5 Excellent
"Clean, quiet and comfortable. An enjoyable stay."
A verified traveller stayed at The Covered Bridge Inn
Posted 2 days ago
The Covered Bridge Inn