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Check prices for these dates

Next weekend
12 June - 14 June
In two weeks
19 June - 21 June
In one month
3 July - 5 July
In two months
31 July - 2 Aug

Our top choices for Winchester bed & breakfast

Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (109 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
The price is AU$218
includes taxes & fees
8 June - 9 June
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Great Place!!!"
United States
page
The price is AU$168
includes taxes & fees
15 June - 16 June
Locust Tree Bed and Breakfast LLC
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (51 reviews)
"My favorite place to stay! Always comfortable and breakfast was great."
United States
Allison
The price is AU$272
includes taxes & fees
7 June - 8 June
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (185 reviews)
"beautiful inn"
United States
Maura
The price is AU$247
includes taxes & fees
23 June - 24 June
Blackberry River Inn
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"Awesome r[m, nice breakfast, excellent staff!"
United States
Julie
The price is AU$247
includes taxes & fees
9 June - 10 June
Simsbury 1820 House
Exterior detail

Peaceful Modern B&B with Comfort & Charm

Peaceful Modern B&B with Comfort & Charm
Harwinton
8.0 out of 10, Very good, (1 review)
The price is AU$252
includes taxes & fees
16 June - 17 June
Peaceful Modern B&B with Comfort & Charm
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AU$463
includes taxes & fees
22 June - 23 June
Manor House Inn
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
The price is AU$1,219
includes taxes & fees
16 June - 17 June
Sunny Peace Homestay
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

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2/10 Terrible
"It's possible that the manager of the property could cancel your reservation without notice and then however could rebook the reservation for $100 plus more. Despicable business practice."
Clasate 3-night trip
Posted 20 hours ago
Americas Best Value Inn Torrington CT

Find out more about Winchester

Winchester B&B information

Number of reviews
1,770
Accommodation
11 B&B
Lowest Price
AU$168
Highest Price
AU$1,219

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, Rowley Fields and Walker Field 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. Locust Tree Bed and Breakfast LLC: 7 rooms. 11.5 mi (18.5 km) from the city centre. Blackberry River Inn: 14 rooms. Situated 8.3 mi (13.3 km) from the heart of Winchester. Enjoy the free cooked breakfast and outdoor pool. 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 Rowley Fields 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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