Photo by Donny Campos

Search B&B in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan
Premium bedding, Tempur-Pedic beds, individually decorated
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (10)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
The price is HK$892
HK$973 total
includes taxes & fees
24 Nov - 25 Nov
Four Columns Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
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
The price is HK$1,224
HK$1,346 total
includes taxes & fees
23 Nov - 24 Nov
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, (164)
"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
The price is HK$1,277
HK$1,386 total
includes taxes & fees
1 Dec - 2 Dec
The Carriage Barn Inn
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is HK$2,074
HK$2,282 total
includes taxes & fees
16 Nov - 17 Nov
Inn on Putney Road
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (172)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
The price is HK$1,350
HK$1,427 total
includes taxes & fees
16 Nov - 17 Nov
Centennial House
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
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
The price is HK$1,905
HK$2,095 total
includes taxes & fees
17 Nov - 18 Nov
The One Cat B&B
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (273)
"The owners are the best. Wonderful place, made with love. "
United States
Adele
Monadnock Inn
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"Warm and inviting atmosphere. Great location. "
United States
Diane
The Engel House
Exterior
Green River Bridge Inn

Green River Bridge Inn

3.0 star property
Guilford
8.4 out of 10, Very good, (13)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
United States
Melissa
The price is HK$1,865
HK$2,033 total
includes taxes & fees
25 Nov - 26 Nov
Green River Bridge Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."
United States
Susan
The price is HK$2,340
HK$2,539 total
includes taxes & fees
16 Nov - 17 Nov
Chesterfield Inn
Outdoor dining
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 HK$2,137
HK$2,733 total
includes taxes & fees
28 Nov - 29 Nov
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great stay"
Jason 1-night trip
Posted 3 days ago
Latchis Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,023
Accommodation
12 B&B
Lowest Price
HK$973
Highest Price
HK$2,724

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cosy environment, a bed and breakfast 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 a good option for your stay?
Every B&B has its own unique feel — whether it's a comfy common area with a fireplace or a beautiful breakfast room, the little 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. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the city centre. Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique decor.
When should I book my B&B in Winchester?
When you're dreaming of a trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Birch Point and Ashuelot River are some notable spots. You should put New England Sweetwater Farm & Distillery and Pisgah State Park on your list if you want to see more of the area.