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B&B in Winchester

Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

3.0 star property
Granby
9.6 out of 10, Exceptional, (101)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
$140 nightly
The price is $155
Dec 5 - Dec 6
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Dec 5 - Dec 6
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$164 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Blackberry River Inn
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
$157 nightly
The price is $176
Dec 9 - Dec 10
Total with taxes and fees
Wilder House Berkshires
Front of property
Simsbury 1820 House

Simsbury 1820 House

4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Very nice room, pleasant and helpful staff"
United States
Concetta
$178 nightly
The price is $204
Dec 7 - Dec 8
Total with taxes and fees
Simsbury 1820 House
Interior detail
Manor House Inn

Manor House Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
$316 nightly
The price is $351
Dec 14 - Dec 15
Total with taxes and fees
Manor House 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.
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Top Winchester Hotel Reviews

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

10/10 Excellent
"Clean comfortable room,great parking and local shopping "
Julie 4-night trip
Posted 8 hours ago
Days Inn by Wyndham Torrington

Find out more about Winchester

Winchester B&B information

Number of reviews
1,825
Accommodation
9 B&B
Lowest Price
$121
Highest Price
$351

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're a solo traveler hoping to get some tips from locals, a B&B can be a good choice for many different types of travelers. If your ideal vacation to Winchester includes spending lots of time outside, Walker Field and Rowley Fields are good spots to enjoy the scenery.
Why consider B&Bs instead of traditional hotels?
Every B&B has a unique charm. Whether it's a picturesque garden or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Winchester?
Here are some well-liked B&Bs in the area: Simsbury 1820 House: 16.5 mi (26.5 km) from the heart of Winchester. Enjoy the designer toiletries and bars. Blackberry River Inn: 14 rooms. 8.3 mi (13.3 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 11.5 mi (18.5 km) from the heart of Winchester. Wilder House Berkshires: 5 rooms. 17.2 mi (27.7 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. Truman Gillet House Bed & Breakfast: 2 rooms. Located 15.9 mi (25.6 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
What's the best time of year to stay at a B&B in Winchester?
When you're planning your stay in Winchester, year-round temperatures and rainfall may be important factors to consider. 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 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Winchester?
Spend some time exploring Highland Lake and Walker Field if you're hoping to see some of the area's natural features. You might put The Marina at Highland Lake and Winchester Historical Society on your list if you want to see more of the area.
How can I get to and around Winchester?
Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) away from the heart of the city. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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