A large rock with carved faces and a river in the background.

Find a Bed and Breakfast in Cheshire County from CA $109

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Top Cities in Cheshire County

A street with historic buildings, a church steeple, and autumn foliage.
B&BB&B

Keene

Keene

Our top choices for Cheshire County bed & breakfast

A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

1. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (296 reviews)
"The building and interior was big on ambiance and charm. The staff was very cordial and helpful. I would suggest the addition of an ice machine"
United States
Jim
The price is CA $192
CA $208 total
includes taxes & fees
Nov 5 - Nov 6
Monadnock Inn
A two-story house with a red door, green shutters, and a snow-covered front yard.

2. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (190 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
The price is CA $236
CA $250 total
includes taxes & fees
Nov 4 - Nov 5
Centennial House
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

3. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is CA $252
CA $274 total
includes taxes & fees
Nov 18 - Nov 19
Stone Hearth Inn and Eatery
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

4. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (138 reviews)
"A very quaint, cozy inn set in West Dover, Vermont. We had a small room but it was clean and comfortable. We didn't choose to order breakfast while we were there but it smelled wonderful! Oz, the host, was professional, pleasant, and helpful."
United States
Ted
The price is CA $64
CA $109 total
includes taxes & fees
Nov 10 - Nov 11
Deerfield Valley Inn
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

5. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (294 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is CA $264
CA $288 total
includes taxes & fees
Oct 29 - Oct 30
Harvest Barn Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

6. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (62 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is CA $138
CA $150 total
includes taxes & fees
Nov 3 - Nov 4
Four Columns Inn
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

7. 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
The price is CA $242
CA $266 total
includes taxes & fees
Oct 28 - Oct 29
Big Bears Lodge
A calm lake reflecting a forest with autumn foliage.

8. 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
The price is CA $192
CA $211 total
includes taxes & fees
Nov 5 - Nov 6
Blue Gentian Lodge at Magic Mountain
A traditional two-story house with a porch and a large tree in front.

9. Follansbee Inn

Follansbee Inn
3.0 star property
North Sutton
9.6 out of 10, Exceptional, (109 reviews)
"Charming, great place for just relaxing"
United States
David
The price is CA $253
CA $274 total
includes taxes & fees
Oct 25 - Oct 26
Follansbee Inn
An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

10. The Wilmington Inn

The Wilmington Inn
3.5 star property
Wilmington
10.0 out of 10, Exceptional, (213 reviews)
"Wonderful property. Great locations. Breakfast was the best of any on our trip!"
United States
Jay
The price is CA $321
CA $363 total
includes taxes & fees
Nov 15 - Nov 16
The Wilmington Inn
A wooden table set with plates, cutlery, and a folded napkin.

11. 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
The price is CA $196
CA $213 total
includes taxes & fees
Oct 28 - Oct 29
The Carriage Barn Inn
A stone fire pit surrounded by a grassy area with a tree and outdoor seating.

12. The Nutmeg

The Nutmeg
3.5 star property
Wilmington
9.4 out of 10, Exceptional, (444 reviews)
"The property was beautiful! Our check in was easy. The room was clean and bedding was very comfortable. Breakfast was also delicious."
United States
Susan
The price is CA $239
CA $263 total
includes taxes & fees
Nov 24 - Nov 25
The Nutmeg
A large white building with a stone wall and a lawn covered in fallen leaves.

13. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (363 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
The price is CA $203
CA $223 total
includes taxes & fees
Oct 27 - Oct 28
Colonel Williams Inn
A bar area with a cake on a glass stand, plates, a pink napkin, and a rolled dessert on a plate.

14. Rosewood Country Inn

Rosewood Country Inn
3.0 star property
Bradford
9.8 out of 10, Exceptional, (106 reviews)
"Amazing inn with wonderful hospitality! Will definitely stay again when we are back in the area."
United States
Monica
The price is CA $288
CA $313 total
includes taxes & fees
Oct 29 - Oct 30
Rosewood Country Inn
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

15. 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
The price is CA $157
CA $172 total
includes taxes & fees
Nov 3 - Nov 4
Doveberry Inn
A well-lit garden area with a gazebo, a small house, and a large tree in the background.

16. Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (121 reviews)
"Enjoyed our stay……breakfast was excellent"
United States
David
The price is CA $296
CA $296 total
includes taxes & fees
Nov 15 - Nov 16
Howarth House B&B
A two-story house with a snow-covered yard and a well-lit front porch.

17. Golden Stage Inn B&B

Golden Stage Inn B&B
3.5 star property
Cavendish
10.0 out of 10, Exceptional, (49 reviews)
"The Golden Stage Inn was one of the highlights of our Vermont trip. Mike and Julie are wonderful hosts and have clearly put so much care into making the entire experience special. Our room was cozy, spacious, and beautifully kept, with a fireplace, lovely bathroom, and one of the most comfortable beds we’ve slept in while traveling. Breakfast alone is a reason to stay here. The two-course breakfasts were phenomenal, with fresh, local ingredients, juice, and plenty of coffee, all served in a...
United States
Andrew
Golden Stage Inn B&B
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

18. 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
Windham Hill Inn
A two-story house with a stone foundation, a white exterior, and a front porch with a railing.

19. Deerhill Inn

Deerhill Inn
3.5 star property
West Dover
9.6 out of 10, Exceptional, (232 reviews)
"Innkeepers were delightful hosts Breakfast was amazing Homemade scones were warm and yummy every day !"
United States
cathlyn
Deerhill Inn
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

20. Dexter's Inn

Dexter's Inn
3.0 star property
Sunapee
8.8 out of 10, Excellent, (70 reviews)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
United States
Lisa
The price is CA $326
CA $353 total
includes taxes & fees
Nov 14 - Nov 15
Dexter's 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire County Hotel Reviews

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Staff is always great Clean room"
PAUL 1-night trip
Posted 3 hours ago
Motel 6 Leominster, MA

Find out more about Cheshire County

Cheshire County B&B information

Number of reviews
2,660
Accommodation
36 B&B
Lowest Price
CA $109
Highest Price
CA $363

Explore a world of travel with Expedia