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B&B in Chester

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (375)
"After working an entire weekend with festivities in the area checking into here for some much needed rest was the best decision we made very comfortable very nice and very clean "
$106 nightly
The price is $117
Aug 26 - Aug 27
Total with taxes and fees
Bromley View Inn

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (228)
"Great stay! "
$248 nightly
The price is $273
Aug 27 - Aug 28
Total with taxes and fees
The Jackson

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (251)
"Staff were very accommodating and wonderful to talk to and get the inside scoop"
$165 nightly
The price is $182
Sep 1 - Sep 2
Total with taxes and fees
The Inn at Manchester

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (134)
"Lovely place to stay Jack and Maryann excellent hosts"
$197 nightly
The price is $217
Aug 26 - Aug 27
Total with taxes and fees
The Inn at Ormsby Hill

Deerfield Valley Inn

3.0 star property
9.6 out of 10, Exceptional, (61)
"Oguz, the manager treated us like family. It was a very pleasant and relaxing stay."
$115 nightly
The price is $127
Sep 8 - Sep 9
Total with taxes and fees
Deerfield Valley Inn

Blue Gentian Lodge at Magic Mountain

2.5 star property
9.2 out of 10, Wonderful, (106)
"Quaintly decorated. Lisa and Ken were very good hosts. Not a modern high tech property, but very homey and welcoming. "
$133 nightly
The price is $147
Aug 27 - Aug 28
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
$169 nightly
The price is $186
Aug 26 - Aug 27
Total with taxes and fees
The Vesper

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
$131 nightly
The price is $145
Sep 11 - Sep 12
Total with taxes and fees
Colonel Williams Inn

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (93)
"Sweet place to stay"
$224 nightly
The price is $244
Aug 26 - Aug 27
Total with taxes and fees
Stone Hearth Inn and Eatery

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Owners are warm and welcoming. Home is charming and well decorated, breakfast excellent. "
The Buckmaster Inn

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (40)
"Superb stay in all ways!"
$249 nightly
The price is $274
Sep 2 - Sep 3
Total with taxes and fees
Stay At Jimmy's

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (51)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
$295 nightly
The price is $324
Aug 26 - Aug 27
Total with taxes and fees
Inn on Putney Road

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (225)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
$136 nightly
The price is $149
Sep 2 - Sep 3
Total with taxes and fees
Harvest Barn Inn

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
$441 nightly
The price is $485
Sep 15 - Sep 16
Total with taxes and fees
Woodbridge Inn

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
$187 nightly
The price is $206
Sep 7 - Sep 8
Total with taxes and fees
Deerhill Inn

Windham Hill Inn

4.0 star property
8.4 out of 10, Very Good, (36)
"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. "
$202 nightly
The price is $221
Aug 27 - Aug 28
Total with taxes and fees
Windham Hill Inn

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!"
$223 nightly
The price is $246
Aug 28 - Aug 29
Total with taxes and fees
The One Cat B&B

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
$185 nightly
The price is $201
Sep 9 - Sep 10
Total with taxes and fees
The Carriage Barn Inn

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 "
$167 nightly
The price is $183
Aug 26 - Aug 27
Total with taxes and fees
Big Bears Lodge

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
$301 nightly
The price is $327
Aug 27 - Aug 28
Total with taxes and fees
Chesterfield 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

Find out more about Chester

Chester B&B information

Number of reviews
147
Accommodation
52 B&B
Lowest Price
$117
Highest Price
$485

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 $117 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.