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

Find Winchester Bed And Breakfast

  • 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
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19
In one month
Jul 31 - Aug 2
In two months
Aug 28 - Aug 30

Our top choices for Winchester bed & breakfast

Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is ￥23,347
￥25,682 total
includes taxes & fees
Jul 5 - Jul 6
Colonel Williams Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ￥26,527
￥28,782 total
includes taxes & fees
Jul 5 - Jul 6
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (45 reviews)
"The hot tub was so amazing"
United States
Mark
The price is ￥33,027
￥35,999 total
includes taxes & fees
Jul 7 - Jul 8
Four Columns Inn
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (287 reviews)
"Lots of character and run by a great family!"
United States
Evan
The price is ￥26,539
￥28,795 total
includes taxes & fees
Jul 15 - Jul 16
Monadnock Inn
Front of property

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 ￥36,576
￥40,234 total
includes taxes & fees
Jul 7 - Jul 8
The One Cat B&B
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
The price is ￥47,530
￥52,284 total
includes taxes & fees
Jul 14 - Jul 15
Inn on Putney Road
Front of property - evening/night

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 ￥48,562
￥52,690 total
includes taxes & fees
Jul 5 - Jul 6
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.
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

The Colonial Hotel

The Colonial Hotel

8/10 Good
"Nice place to stay at. Wishing cofffee in lobby was gratuitous."
Kenneth 4-night trip
Posted 8 hours ago
The Colonial Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,105
Accommodation
12 B&B
Lowest Price
￥25,682
Highest Price
￥52,690

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 well-liked B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester.Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Inn on Putney Road: 6 rooms. 10.7 mi (17.3 km) from the heart of downtown. Enjoy the free full breakfast and onsite spa services. The Carriage Barn Inn: 4 rooms. Located 11.8 mi (18.9 km) from the core of Winchester.
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 Winchester Speedpark and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.

Explore a world of travel with Expedia