Search Winchester Bed & Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Winchester 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, (413 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AU$181
includes taxes & fees
20 Jan - 21 Jan
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, (102 reviews)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is AU$233
includes taxes & fees
20 Jan - 21 Jan
Truman Gillet House Bed & Breakfast
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (42 reviews)
"It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous "
United States
Evan M
The price is AU$304
includes taxes & fees
20 Jan - 21 Jan
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AU$283
includes taxes & fees
20 Jan - 21 Jan
Blackberry River Inn
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,004 reviews)
"Lovely staff, beautiful room, comfy bed, delicious fresh breakfast. "
United States
Debra
The price is AU$299
includes taxes & fees
20 Jan - 21 Jan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"The staff were very helpful.The had a great breakfast and clean tables. The room was very clean.They had coffee and flavored drinks at a station when you came in.This was a very good stay."
Robert 1-night trip
Posted 3 days ago
The Farmington Inn & Suites

Find out more about Winchester

Winchester B&B information

Number of reviews
1,706
Accommodation
9 B&B
Lowest Price
AU$181
Highest Price
AU$304

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. Wilder House Berkshires: 5 rooms. Situated 17.2 mi (27.7 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique decor. Locust Tree Bed and Breakfast LLC: 7 rooms. 11.5 mi (18.5 km) from the city centre. 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 The Marina at Highland Lake 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.

Explore a world of travel with Expedia