A snow-covered town with a river running through it, surrounded by mountains and trees.

Search B&B in Winchester

  • 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
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Winchester bed & breakfast

Free daily continental breakfast

1. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is AED 537
AED 582 total
includes taxes & fees
10 Aug - 11 Aug
The Carriage Barn Inn
Front of property

2. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AED 891
AED 980 total
includes taxes & fees
9 Aug - 10 Aug
The One Cat B&B
Front of property

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is AED 579
AED 636 total
includes taxes & fees
9 Aug - 10 Aug
Colonel Williams Inn
Exterior

4. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (59 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is AED 1,083
AED 1,191 total
includes taxes & fees
10 Aug - 11 Aug
Inn on Putney Road
Front of property - evening/night

5. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
20 Aug - 21 Aug
Chesterfield Inn
Exterior

6. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (289 reviews)
"Castine is a great host, and the inn has a lot of New England charm. Great place to stay!"
United States
Saif
The price is AED 620
AED 673 total
includes taxes & fees
6 Aug - 7 Aug
Monadnock Inn
Land view from property

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (49 reviews)
"Can’t go wrong with this place."
United States
John
The price is AED 933
AED 1,017 total
includes taxes & fees
12 Aug - 13 Aug
Four Columns Inn
Outdoor dining

8. Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
The price is AED 1,010
AED 1,292 total
includes taxes & fees
12 Aug - 13 Aug
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Terrace/patio

9. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is AED 1,036
AED 1,036 total
includes taxes & fees
26 Aug - 27 Aug
The Maguire House Bed & Breakfast
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 Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Super fun environment. Wish we had more time to stay there. In the middle of nowhere yet still close to food places and other activities."
Kathleen 1-night trip
Posted 13 hours ago
Vikings Villages Resort

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your trip to Winchester. While you're enjoying your trip to Winchester, Loring Field and Richmond Wildlife Manangement Area are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel. Whether it's a cozy reading space or a beautiful breakfast room, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Below are some B&Bs in the area: Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the downtown core. Enjoy the local cuisine breakfast and library. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Loring Field and Birch Point are some notable spots. You might put New England Sweetwater Farm & Distillery and Conant Public Library on your list if you want to see more of the area.

Explore a world of travel with Expedia