Bed and Breakfast in Chester

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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured B&B in Chester

Stone Hearth Inn and Eatery
Classic two-story house with a traditional gabled roof and chimney, set amidst a beautifully maintained garden.

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (90)
"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 NZ$304
includes taxes & fees
23 July - 24 July
Stone Hearth Inn and Eatery
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Relax in style with a comfortable leather armchair and a fireplace, surrounded by a cozy reading nook and a dining area.

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 NZ$349
includes taxes & fees
13 July - 14 July
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Room in Historic Inn! 20 Minutes to Okemo!
Relax on the porch with wicker chairs and a small table, surrounded by windows with shutters.

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (15)
"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 NZ$308
includes taxes & fees
20 July - 21 July
Room in Historic Inn! 20 Minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Relax in style with a comfortable seating area, fireplace, and dining space, perfect for leisure activities and enjoying a view of the outdoors.

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is NZ$379
includes taxes & fees
14 July - 15 July
King & Queen Suite in Historic Inn Circa 1780
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"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 NZ$288
includes taxes & fees
23 July - 24 July
The Carriage Barn Inn
Chesterfield Inn
Cozy living room with a rustic fireplace, large windows, and classic furnishings.

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is NZ$545
includes taxes & fees
24 July - 25 July
Chesterfield Inn
Harvest Barn Inn
Enjoy a serene lake view from the balcony, where two Adirondack chairs await.

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (221)
"Very accommodating and wonderful people! Hoping to return!"
Harvest Barn Inn
The One Cat B&B
Welcome to this charming home, featuring a cozy porch with lush greenery, potted plants, and a traditional gabled roof.

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 NZ$400
includes taxes & fees
14 July - 15 July
The One Cat B&B
Inn on Putney Road
Classic two-story house with a gabled roof and symmetrical facade, surrounded by a well-maintained garden and a white fence.

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (47)
"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 NZ$486
includes taxes & fees
13 July - 14 July
Inn on Putney Road
Colonel Williams Inn
Stunning hotel set amidst a serene autumn landscape.

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is NZ$249
includes taxes & fees
28 July - 29 July
Colonel Williams Inn
Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (35)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is NZ$456
includes taxes & fees
21 July - 22 July
Stay At Jimmy's
The Vesper
Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (24)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is NZ$279
includes taxes & fees
16 July - 17 July
The Vesper
The Jackson
Cozy space with a fireplace, sofa, and coffee table, perfect for unwinding.

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (217)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
The Jackson
Windham Hill Inn
Surrounded by lush greenery, this serene landscape offers a peaceful escape.

Windham Hill Inn

4.0 star property
8.4 out of 10, Very good, (35)
"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 NZ$330
includes taxes & fees
13 July - 14 July
Windham Hill Inn
Deerhill Inn
Stunning two-story house with a front porch and stone wall, set amidst a lush lawn.

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Never disappoints!"
The price is NZ$346
includes taxes & fees
10 Aug - 11 Aug
Deerhill Inn
Blue Gentian Lodge at Magic Mountain
Surrounded by a dense forest, this serene lakeside setting offers a peaceful escape.

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (102)
"The most comfortable stay I have had in a long time. I look forward to visiting the Blue Gentian Lodge again!"
The price is NZ$310
includes taxes & fees
11 July - 12 July
Blue Gentian Lodge at Magic Mountain
Deerfield Valley Inn
Enjoy a warm gathering by the fire pit in a serene natural setting.

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (50)
"Overall great spot!"
Deerfield Valley Inn
Echo Lake Inn
Classic hotel with a central entrance and symmetrical facade.

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 NZ$352
includes taxes & fees
15 July - 16 July
Echo Lake Inn
Big Bears Lodge
Relax in a hot tub surrounded by a wooden deck and a serene grassy area.

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 NZ$306
includes taxes & fees
10 Aug - 11 Aug
Big Bears Lodge
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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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?
Here are some well-liked B&Bs in the 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 decor. Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!: 0.3 mi (0.4 km) from the city centre. Bromley View Inn: 16 rooms. Located 17.8 mi (28.6 km) from the core of Chester. 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 Lowell Lake State Park 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.