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Our top choices for Chester bed & breakfast

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
$191 nightly
The price is $208
May 21 - May 22
Total with taxes and fees
Stone Hearth Inn and Eatery

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (442 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
$89 nightly
The price is $97
May 19 - May 20
Total with taxes and fees
Bromley View Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
$146 nightly
The price is $161
Jun 3 - Jun 4
Total with taxes and fees
Colonel Williams Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
$126 nightly
The price is $138
May 19 - May 20
Total with taxes and fees
Four Columns Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
$189 nightly
The price is $205
May 19 - May 20
Total with taxes and fees
The Carriage Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (264 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
$151 nightly
The price is $165
May 25 - May 26
Total with taxes and fees
Harvest Barn Inn

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (280 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
$152 nightly
The price is $167
May 20 - May 21
Total with taxes and fees
The Jackson

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
$244 nightly
The price is $268
May 26 - May 27
Total with taxes and fees
The One Cat B&B

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (61 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
$197 nightly
The price is $217
May 31 - Jun 1
Total with taxes and fees
The Vesper

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (118 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
$149 nightly
The price is $164
May 28 - May 29
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (313 reviews)
"Staff was exceptionally friendly…lovely Inn! Beautiful views "
United States
Michael
$140 nightly
The price is $153
May 26 - May 27
Total with taxes and fees
The Inn at Manchester

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (118 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
$105 nightly
The price is $116
Jun 2 - Jun 3
Total with taxes and fees
Deerfield Valley Inn

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$117 nightly
The price is $129
May 27 - May 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1 review)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
$114 nightly
The price is $125
May 20 - May 21
Total with taxes and fees
Room 7 - family room sleeps 4

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
$253 nightly
The price is $279
Jun 2 - Jun 3
Total with taxes and fees
Deer Brook Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
$210 nightly
The price is $229
Jun 1 - Jun 2
Total with taxes and fees
Echo Lake Inn

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (214 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
$173 nightly
The price is $190
May 19 - May 20
Total with taxes and fees
Big Bears Lodge

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
$284 nightly
The price is $312
May 19 - May 20
Total with taxes and fees
Inn on Putney Road

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
$197 nightly
The price is $214
Jun 11 - Jun 12
Total with taxes and fees
Windham Hill Inn

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (161 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$259 nightly
The price is $285
May 27 - May 28
Total with taxes and fees
The Inn at Ormsby Hill
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

Find out more about Chester

Chester B&B information

Number of reviews
1,970
Accommodation
77 B&B
Lowest Price
$97
Highest Price
$312

Frequently asked questions

What are the most popular Chester Bed and Breakfasts?
The King & Queen Suite in Historic Inn Circa 1780 is a fantastic option for travelers seeking a blend of history and modern comfort, boasting an impressive rating of 9.6. This charming property features a kitchenette equipped with a refrigerator, toaster, and microwave, making it easy to prepare meals during your stay. With a lovely patio area for relaxation and the nearby mountains inviting you for outdoor adventures like hiking and biking, it's great for couples or solo travelers looking to unwind in a tranquil setting.

For those planning a ski trip or family adventure, the Room in Historic Inn. 20 Minutes to Okemo. is a wonderful choice, rated 9.4. It offers a cozy space with a well-appointed kitchenette and a charming porch to enjoy the fresh Vermont air. The location is ideal for both summer hiking and winter sports, ensuring that families can create lasting memories together in the great outdoors.

Families will also appreciate the Stone Hearth Inn and Eatery, which comes highly recommended with a score of 9.2. Known for its delightful breakfast, including the famous blueberry French toast, this inn offers a warm and friendly space. With beautiful grounds for children to explore and easy access to nearby skiing and hiking, it's a great home base for adventure-seeking families.
What is the nightly rate for a Bed & Breakfast in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $97 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Are there any family-friendly B&Bs in Chester?
The King & Queen Suite in Historic Inn Circa 1780 is a delightful choice for families visiting Chester. This charming property, steeped in history, features a kitchenette and a cozy patio, great for relaxing after a day of adventures. Families will appreciate the thoughtful amenities tailored for children, including games and dinnerware specifically designed for little ones, ensuring that everyone feels at home.

For an equally family-friendly option, consider the Room in Historic Inn. Just 20 minutes from Okemo, this inviting space offers a sofa bed, making it great for families needing extra sleeping arrangements. It also includes a kitchenette and a microwave for those convenient snack time moments, along with a lovely patio to enjoy the fresh Vermont air.

Another standout is the Stone Hearth Inn and Eatery, which truly caters to families. With a free buffet breakfast to start the day, children will love the selection of books and games available, along with complimentary cribs and highchairs. Its garden area provides a lovely outdoor space for kids to play while parents unwind. This property combines comfort and convenience, making it an excellent home base for family adventures in Chester.
Which area is best to stay in a Chester B&B?
Chester Depot is the standout area for travelers seeking a B&B experience in Chester, Vermont. Families will appreciate the quaint charm and relaxed atmosphere that this neighborhood offers, making it easy to explore together. The nearby Green Mountain National Forest provides ample opportunities for outdoor adventures, including hiking and biking trails suitable for all ages.

Cultural experiences abound, with the historic Chester Village and its classic New England architecture just a short drive away. Visitors can enjoy local artisan shops and seasonal farmers' markets, superb for sampling regional produce and crafts. For a bit of fun, families can also venture to the nearby Magic Mountain Ski Area during winter months for skiing and snowboarding.

For couples looking for a peaceful retreat, Chester Depot's scenic beauty is ideal. Stroll through the picturesque countryside or relax at one of the local cafes, soaking in the tranquil Vermont ambiance.
When is the best time to book a B&B in Chester?
The most popular time to book a B&B in Chester is during the summer months, particularly from July to September. This peak season attracts visitors eager to embrace the region's natural beauty, as well as its array of outdoor activities. With warm temperatures ranging from the mid-60s to the high 80s Fahrenheit, it's an ideal time for hiking, fishing, and exploring the picturesque landscapes surrounding Lake Almanor.

July stands out as the busiest month, where you can join fellow travelers in enjoying the vibrant atmosphere. The area comes alive with family-friendly festivals and events, making it a great time for those seeking a lively and social experience. Whether you're interested in water sports on the lake or leisurely strolls through local shops, there's something for everyone.

For travelers looking for a more budget-friendly option, consider visiting Chester in March. This month offers a quieter experience, where you can appreciate the serene beauty of the spring thaw. While the temperatures can be cooler, ranging from the low 30s to mid-50s Fahrenheit, it's a wonderful opportunity for those who enjoy a peaceful getaway and fewer crowds.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.

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