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Find a Bed and Breakfast in Winchester from CA $169

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Winchester bed & breakfast

Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (194 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is CA $192
CA $221 total
includes taxes & fees
Jul 20 - Jul 21
Blackberry River Inn
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (434 reviews)
"Below average B&B"
United States
Larry
The price is CA $147
CA $169 total
includes taxes & fees
Jul 27 - Jul 28
Locust Tree Bed and Breakfast LLC
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (113 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
The price is CA $196
CA $218 total
includes taxes & fees
Jul 21 - Jul 22
Truman Gillet House Bed & Breakfast
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is CA $446
CA $495 total
includes taxes & fees
Jul 29 - Jul 30
Manor House Inn
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (9 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
The price is CA $173
CA $280 total
includes taxes & fees
Aug 1 - Aug 2
Sunny Peace Homestay
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (57 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $268
CA $299 total
includes taxes & fees
Jul 19 - Jul 20
Wilder House Berkshires
Exterior

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful historical hotel Room was lovely Staff friendly and helpful"
United States
FRANK
The price is CA $308
CA $378 total
includes taxes & fees
Jul 22 - Jul 23
Simsbury 1820 House
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"The inn was beautifully appointed and very clean. We enjoyed the pool also. Highly recommend."
Suzanne 1-night trip
Posted 3 hours ago
The Litchfield Inn

Find out more about Winchester

Winchester B&B information

Number of reviews
1,946
Accommodation
11 B&B
Lowest Price
CA $169
Highest Price
CA $495

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 Platt Hill State Park 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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