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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

Featured B&B in Winchester

Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (406)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
The price is AU$186
includes taxes & fees
21 Oct - 22 Oct
Locust Tree Bed and Breakfast LLC
Property grounds
Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & Breakfast
3.0 star property
9.6 out of 10, Exceptional, (96)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is AU$239
includes taxes & fees
22 Oct - 23 Oct
Truman Gillet House Bed & Breakfast
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (147)
"A wonderful facility, lovely breakfast and way way more than you would expect in every catagory."
United States
Steve
The price is AU$291
includes taxes & fees
21 Oct - 22 Oct
Blackberry River Inn
Wilder House Berkshires Room 3
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (36)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
The price is AU$245
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
Front of property
Simsbury 1820 House
Simsbury 1820 House
4.0 star property
9.2 out of 10, Wonderful, (1001)
"A beautiful place to enjoy the many sights of the area from."
United States
Robert
The price is AU$316
includes taxes & fees
2 Nov - 3 Nov
Simsbury 1820 House
Interior detail
Manor House Inn
Manor House Inn
3.0 star property
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AU$481
includes taxes & fees
19 Nov - 20 Nov
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

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

10/10 Excellent
"Friendly and helpful staff. Clean room. Safe and well maintained environment. "
Pamela 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Plainville

Find out more about Winchester

Winchester B&B information

Number of reviews
1,788
Accommodation
9 B&B
Lowest Price
AU$186
Highest Price
AU$481

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're a solo traveller hoping to make some connections, B&Bs can be a great choice for many types of holidaymakers. If your ideal holiday to Winchester includes spending lots of time outside, Walker Field and Rowley Fields are good spots to enjoy the scenery.
Why should you consider a B&B versus a traditional hotel?
B&Bs all have a unique charm — whether it's a garden for guests to admire or a sunlit breakfast nook, the tiny details are what make bed and breakfasts the perfect escape.
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 city centre. 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 city centre. Enjoy the free cooked breakfast and unique decor. 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 decor.
What's the best time of year to stay at a B&B in Winchester?
When you're planning your getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm 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 should put Burr Pond State Park and Platt Hill State Park on your list if you want to see more of the area.
How can I get to and around Winchester?
You can map out your trip in and around Winchester ahead of time with these transportation options. Fly into Hartford, CT (BDL-Bradley Intl.), which is located 21.9 mi (35.2 km) from the city centre. You can also search for flights into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, consider renting a car to explore more sights.

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