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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Winchester

Dining
Four Columns Inn
Four Columns Inn
3.0 star property
9.6 out of 10, Exceptional, (8)
"Lovely staff, amazing ambiance!"
United States
Julie
Four Columns Inn
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (336)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 532
AED 585 total
includes taxes & fees
3 Nov - 4 Nov
Colonel Williams Inn
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (162)
"Great BB. Very charming and cozy! Will definitely stay again! "
United States
Maria
The price is AED 664
AED 721 total
includes taxes & fees
20 Nov - 21 Nov
The Carriage Barn Inn
Exterior
The One Cat B&B
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AED 891
AED 980 total
includes taxes & fees
16 Nov - 17 Nov
The One Cat B&B
Exterior
Green River Bridge Inn
Green River Bridge Inn
3.0 star property
9.0 out of 10, Wonderful, (11)
"Beautiful Inn and property"
United States
JaDean
The price is AED 915
AED 997 total
includes taxes & fees
1 Nov - 2 Nov
Green River Bridge Inn
Exterior
Inn on Putney Road
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (55)
"Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries."
United States
Gianfranco
The price is AED 980
AED 1,078 total
includes taxes & fees
2 Nov - 3 Nov
Inn on Putney Road
Free daily full breakfast
Centennial House
Centennial House
3.5 star property
9.6 out of 10, Exceptional, (171)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
The price is AED 659
AED 697 total
includes taxes & fees
5 Nov - 6 Nov
Centennial House
Exterior
Monadnock Inn
Monadnock Inn
2.5 star property
7.6 out of 10, Good, (272)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Exterior
The Engel House
The Engel House
3.0 star property
9.2 out of 10, Wonderful, (15)
"The perfect Vermont Bed and Breakfast. "
United States
Lee
The Engel House
Property grounds
The Maguire House Bed & Breakfast
The Maguire House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (36)
"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 980
AED 980 total
includes taxes & fees
12 Nov - 13 Nov
The Maguire House Bed & Breakfast
Lobby
Chesterfield Inn
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
2 Nov - 3 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.
The price is AED 1,010
AED 1,288 total
includes taxes & fees
31 Oct - 1 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.
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Top Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Unique, well executed hotel concept in an unbelievably beautiful area. Easy drive to restaurants. Clean room, friendly staff, easy access. We loved it!"
Michael 2-night trip
Posted 21 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, Rhododendron State Park and Loring Field 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. Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the deli and patio area. Monadnock Inn: 11 rooms. Located 17.2 mi (27.6 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, Rhododendron State Park and Ashuelot River are some notable spots. You might put Pisgah State Park and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.