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B&B in Chester

Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
$200 nightly
The price is $219
Dec 4 - Dec 5
Total with taxes and fees
Stone Hearth Inn and Eatery
Room in Historic Inn! 20 Minutes to Okemo!
9.2 out of 10, Wonderful, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
$149 nightly
The price is $167
Nov 6 - Nov 7
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
9.0 out of 10, Wonderful, (2)
"Yes, wonderful location and stay"
United States
Sharon
$144 nightly
The price is $161
Nov 6 - Nov 7
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
$202 nightly
The price is $226
Nov 6 - Nov 7
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
$159 nightly
The price is $178
Nov 6 - Nov 7
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Bromley View Inn
3.5 star property
9.0 out of 10, Wonderful, (398)
"Breakfast , beverages and hot tub were nice in addition to the family game room area. "
United States
Lynn
$89 nightly
The price is $97
Nov 9 - Nov 10
Total with taxes and fees
Bromley View Inn
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (243)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$166 nightly
The price is $181
Nov 24 - Nov 25
Total with taxes and fees
Harvest Barn Inn
Four Columns Inn
4.0 star property
9.6 out of 10, Exceptional, (9)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$170 nightly
The price is $186
Nov 18 - Nov 19
Total with taxes and fees
Four Columns Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
$150 nightly
The price is $166
Nov 19 - Nov 20
Total with taxes and fees
Colonel Williams Inn
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (163)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
$179 nightly
The price is $195
Dec 1 - Dec 2
Total with taxes and fees
The Carriage Barn Inn
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (147)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
$173 nightly
The price is $191
Nov 12 - Nov 13
Total with taxes and fees
The Inn at Ormsby Hill
The Jackson
4.0 star property
9.8 out of 10, Exceptional, (240)
"Great stay! "
United States
Romulo
$175 nightly
The price is $193
Nov 6 - Nov 7
Total with taxes and fees
The Jackson
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (275)
"The staff was so friendly and helpful. Would definitely recommend. "
United States
Christine
$165 nightly
The price is $182
Nov 6 - Nov 7
Total with taxes and fees
The Inn at Manchester
Deerfield Valley Inn
3.0 star property
9.6 out of 10, Exceptional, (82)
"We had a lovely time staying here. "
United States
Jeff
$93 nightly
The price is $103
Nov 23 - Nov 24
Total with taxes and fees
Deerfield Valley Inn
Windham Hill Inn
4.0 star property
8.6 out of 10, Excellent, (37)
"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. "
United States
Brandon
$189 nightly
The price is $206
Nov 10 - Nov 11
Total with taxes and fees
Windham Hill Inn
The Vesper
3.0 star property
9.0 out of 10, Wonderful, (41)
"The location is fabulous bc you can walk everywhere once you arrive. Beds were comfortable and great options at breakfast(the oats and fresh strawberries were my favorite)"
United States
Abigail
$163 nightly
The price is $180
Nov 12 - Nov 13
Total with taxes and fees
The Vesper
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
$199 nightly
The price is $219
Nov 10 - Nov 11
Total with taxes and fees
Stay At Jimmy's
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
$243 nightly
The price is $268
Nov 9 - Nov 10
Total with taxes and fees
The One Cat B&B
Big Bears Lodge
3.0 star property
9.0 out of 10, Wonderful, (185)
"The property is conveniently located in close proximity to Mt Snow and local restaurants. The staff is friendly. There's a big screen tv room with fireplace and a small sitting room to read or just converse. Rooms are a little dated but clean. Would stay again."
United States
Jonathan
$167 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Big Bears Lodge
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (55)
"Pricey but overall. A wonderful stay. Excellent breakfast, grounds, shower and inn keeper."
United States
Jane
$267 nightly
The price is $294
Nov 6 - Nov 7
Total with taxes and fees
Inn on Putney Road
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
2,435
Accommodation
52 B&B
Lowest Price
$97
Highest Price
$294

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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