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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, (108)
"Great stay at this cozy inn! The innkeeper was very helpful and attentive. The breakfasts were delicious. Comfortable and clean! It would be nice to visit it again in the summer."
United States
Helen
$230 nightly
The price is $251
Jan 5 - Jan 6
Total with taxes and fees
Stone Hearth Inn and Eatery

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (16)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
$129 nightly
The price is $141
Jan 4 - Jan 5
Total with taxes and fees
Four Columns Inn

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (406)
"Clean and great location with fun lounge area."
United States
Marshall
$118 nightly
The price is $130
Jan 4 - Jan 5
Total with taxes and fees
Bromley View Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$144 nightly
The price is $158
Jan 13 - Jan 14
Total with taxes and fees
Harvest Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (166)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
$129 nightly
The price is $141
Jan 19 - Jan 20
Total with taxes and fees
The Carriage Barn Inn

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
$122 nightly
The price is $135
Feb 1 - Feb 2
Total with taxes and fees
The One Cat B&B

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
$143 nightly
The price is $158
Jan 6 - Jan 7
Total with taxes and fees
Colonel Williams Inn

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (282)
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
United States
Amy
$165 nightly
The price is $182
Jan 4 - Jan 5
Total with taxes and fees
The Inn at Manchester

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
"Lovely pleasant stay. "
United States
Heather
$168 nightly
The price is $185
Jan 5 - Jan 6
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (38)
"Did not use"
United States
Douglas
$179 nightly
The price is $196
Jan 19 - Jan 20
Total with taxes and fees
Windham Hill Inn

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (259)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
$199 nightly
The price is $219
Jan 5 - Jan 6
Total with taxes and fees
The Jackson

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
$178 nightly
The price is $196
Jan 4 - Jan 5
Total with taxes and fees
Big Bears Lodge

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
$249 nightly
The price is $274
Jan 4 - Jan 5
Total with taxes and fees
Stay At Jimmy's

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
$235 nightly
The price is $258
Jan 4 - Jan 5
Total with taxes and fees
Inn on Putney Road

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
"Charming bed and breakfast"
United States
Nicholas
$154 nightly
The price is $170
Jan 5 - Jan 6
Total with taxes and fees
The Vesper

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
$124 nightly
The price is $137
Jan 4 - Jan 5
Total with taxes and fees
Room 7 - family room sleeps 4

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (151)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$262 nightly
The price is $289
Jan 5 - Jan 6
Total with taxes and fees
The Inn at Ormsby Hill

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
$307 nightly
The price is $334
Jan 13 - Jan 14
Total with taxes and fees
Chesterfield Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (91)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
$187 nightly
The price is $206
Jan 5 - Jan 6
Total with taxes and fees
Deerfield Valley Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
$259 nightly
The price is $283
Jan 6 - Jan 7
Total with taxes and fees
Echo Lake 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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Top Chester Hotel Reviews

Find out more about Chester

Chester B&B information

Number of reviews
2,698
Accommodation
62 B&B
Lowest Price
$130
Highest Price
$334

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 $130 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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