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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 53 B&B in Chester with updated reviews, rates, and availability.

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (212)
"The hotel is great, the rooms are large and comfortable, the steep stairs are not for the faint hearted. "
The price is AED 820
AED 902 total
includes taxes & fees
4 May - 5 May
The Jackson
Bromley View Inn
Lounge

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (342)
"It was nice that they had a pool table in the common area."
The price is AED 433
AED 477 total
includes taxes & fees
11 May - 12 May
Bromley View Inn
Big Bears Lodge
Outdoor spa tub

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 AED 612
AED 674 total
includes taxes & fees
4 May - 5 May
Big Bears Lodge
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.8 out of 10, Exceptional, (17)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is AED 606
AED 667 total
includes taxes & fees
4 May - 5 May
The Vesper
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (118)
"Really liked the beautiful interior of the inn."
The price is AED 572
AED 629 total
includes taxes & fees
4 May - 5 May
The Inn at Ormsby Hill
The Inn at Manchester
Property grounds

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (236)
"Amazing as always! Such a lovely place to stay and the breakfast is absolutely delicious. "
The price is AED 569
AED 626 total
includes taxes & fees
4 May - 5 May
The Inn at Manchester
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (303)
"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 AED 567
AED 618 total
includes taxes & fees
5 May - 6 May
Colonel Williams Inn
Deerfield Valley Inn
Exterior

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (50)
"Nice quiet bed and breakfast. Staff was great. Walking distance to three restaurants. "
The price is AED 312
AED 444 total
includes taxes & fees
5 May - 6 May
Deerfield Valley Inn
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"Amazing property! Absolutely will return again"
The price is AED 715
AED 787 total
includes taxes & fees
8 May - 9 May
Deerhill Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (29)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is AED 1,098
AED 1,208 total
includes taxes & fees
4 May - 5 May
Stay At Jimmy's
Windham Hill Inn
Romantic Room, 1 King Bed | Mountain view

Windham Hill Inn

3.5 star property
8.4 out of 10, Very Good, (33)
"Amazing trip. Beautiful property. Hope to return someday. "
The price is AED 665
AED 725 total
includes taxes & fees
15 May - 16 May
Windham Hill Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is AED 644
AED 699 total
includes taxes & fees
5 May - 6 May
The Carriage Barn Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (210)
"Nice and comfortable great breakfast"
The price is AED 739
AED 806 total
includes taxes & fees
9 May - 10 May
Harvest Barn Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (89)
"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 AED 1,218
AED 1,327 total
includes taxes & fees
5 May - 6 May
Stone Hearth Inn and Eatery
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is AED 720
AED 784 total
includes taxes & fees
26 May - 27 May
Echo Lake Inn
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (45)
"Excellent"
The price is AED 1,043
AED 1,148 total
includes taxes & fees
4 May - 5 May
Inn on Putney Road
Blue Gentian Lodge at Magic Mountain
Kayaking

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (98)
"A great room close to the slopes; warm and comfortable; breakfast that was included was simple but home cooked and amazing."
Blue Gentian Lodge at Magic Mountain
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

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 AED 474
AED 749 total
includes taxes & fees
13 May - 14 May
Honeymoon Suite with Jacuzzi Tub in Historic Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Four Columns Inn
Deluxe Room | Living area | 20-inch TV with cable channels

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns 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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Other property types in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Miscellaneous

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"Peaceful vacation"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is AED 744
AED 2,365 total
includes taxes & fees
4 May - 5 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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.

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 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 décor. Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!: 0.3 mi (0.4 km) from the downtown core. Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the heart of downtown. 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 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 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.