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Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
$215 nightly
The price is $235
Nov 13 - Nov 14
Total with taxes and fees
Stone Hearth Inn and Eatery

2. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (292 reviews)
"The breakfasts were amazing and the hosts were super kind and helpful!"
United States
gail
$142 nightly
The price is $155
Nov 3 - Nov 4
Total with taxes and fees
Harvest Barn Inn

3. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (126 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
$149 nightly
The price is $164
Nov 3 - Nov 4
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain

4. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (495 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
$89 nightly
The price is $97
Nov 1 - Nov 2
Total with taxes and fees
Bromley View Inn

5. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (61 reviews)
"Super cute place, if you love being In a hallmark movie you will love this place. Each room is named after a celebrity guest, Paul Newman, Tom Cruise...the restaurant was great, got free appetizers and breakfast included. Staff are very nice and helpful. Would definitely recommend a stay even if for 1 night."
United States
cindy
$96 nightly
The price is $105
Nov 2 - Nov 3
Total with taxes and fees
Four Columns Inn

6. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (47 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
$207 nightly
The price is $225
Oct 26 - Oct 27
Total with taxes and fees
Windham Hill Inn

7. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (331 reviews)
"Amazing stay and great restaurant!"
United States
Ava
$176 nightly
The price is $194
Nov 3 - Nov 4
Total with taxes and fees
The Jackson

8. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.8 out of 10, Excellent, (106 reviews)
"Beautiful property! The charm and character of the place were amazing. Staff was friendly and very helpful. Rooms were quaint and well appointed, clean with comfy beds!"
United States
Amanda
$305 nightly
The price is $333
Oct 14 - Oct 15
Total with taxes and fees
Echo Lake Inn

9. Doveberry Inn

Doveberry Inn
3.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
$111 nightly
The price is $122
Nov 9 - Nov 10
Total with taxes and fees
Doveberry Inn

10. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (391 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
$178 nightly
The price is $196
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Manchester

11. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (134 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
$81 nightly
The price is $89
Nov 12 - Nov 13
Total with taxes and fees
Deerfield Valley Inn

12. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (80 reviews)
$165 nightly
The price is $182
Nov 10 - Nov 11
Total with taxes and fees
The Vesper

13. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
$220 nightly
The price is $242
Nov 1 - Nov 2
Total with taxes and fees
Deer Brook Inn

14. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (362 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
$143 nightly
The price is $158
Nov 3 - Nov 4
Total with taxes and fees
Colonel Williams Inn

15. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
$177 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
The Carriage Barn Inn

16. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (220 reviews)
"Welcoming host with great customer service"
United States
Alfred
$173 nightly
The price is $190
Oct 28 - Oct 29
Total with taxes and fees
Big Bears Lodge

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

18. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
$299 nightly
The price is $329
Oct 29 - Oct 30
Total with taxes and fees
Stay At Jimmy's

19. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
$267 nightly
The price is $294
Nov 1 - Nov 2
Total with taxes and fees
Inn on Putney Road

20. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
8.0 out of 10, Very good, (2 reviews)
"Great place! Loved the shared full kitchen! Loved all the seating outdoors to enjoy the mountains!!! Was centrally located to enjoy surrounding areas. Host was very responsive to questions."
United States
Cheryl C.
$134 nightly
The price is $148
Nov 2 - Nov 3
Total with taxes and fees
3, cozy pet friendly Vermont retreat - two doubles
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
2,426
Accommodation
65 B&B
Lowest Price
$89
Highest Price
$333

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 $89 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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