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Check prices for these dates

Next weekend
31 July - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sept - 20 Sept

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, (197 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is AU$243
includes taxes & fees
28 July - 29 July
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, (435 reviews)
"Below average B&B"
United States
Larry
The price is AU$173
includes taxes & fees
8 Aug - 9 Aug
Locust Tree Bed and Breakfast LLC
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 AU$515
includes taxes & fees
27 July - 28 July
Manor House Inn
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (114 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
The price is AU$222
includes taxes & fees
3 Aug - 4 Aug
Truman Gillet House Bed & Breakfast
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (58 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AU$281
includes taxes & fees
27 July - 28 July
Wilder House Berkshires
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 AU$293
includes taxes & fees
12 Aug - 13 Aug
Sunny Peace Homestay
Exterior

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,001 reviews)
"Beautiful historical hotel Room was lovely Staff friendly and helpful"
United States
FRANK
The price is AU$417
includes taxes & fees
3 Aug - 4 Aug
Simsbury 1820 House
Exterior detail

Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
9.4 out of 10, Exceptional, (3 reviews)
"We had a very comfortable stay . Communication with our host was easy & prompt. We would stay again “"
United States
Laurel B.
The price is AU$258
includes taxes & fees
17 Aug - 18 Aug
Peaceful Modern Private Room with Comfort & Charm
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

8/10 Good
"We found the room to be nice and everything was clean. The bathroom was just OK something was sticky on the floor and we kept squeaking in there. There was no soap in the body wash dispenser which was remedied quickly. Also fpound the A/C unit in the room noisy. I asked about this and someone was going to come and check. Nothing changed so I assume that was normal. The breakfast area in the morning was well maintained and there were a variety of things to eat both hot and cold. The woman down there did a heck of a job keeping everything fresh and stocked. Parking was adequate."
CURT 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Plainville

Find out more about Winchester

Winchester B&B information

Number of reviews
1,460
Accommodation
11 B&B
Lowest Price
AU$173
Highest Price
AU$515

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 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?
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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