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Find a Bed and Breakfast in Winchester from CA $167

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Winchester bed & breakfast

Library

1. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (215 reviews)
"The Inn is lovely and charming - and the breakfast was especially great."
United States
Rachel
The price is CA $201
CA $232 total
includes taxes & fees
Sep 17 - Sep 18
Blackberry River Inn
Exterior

2. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (443 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
The price is CA $145
CA $167 total
includes taxes & fees
Sep 9 - Sep 10
Locust Tree Bed and Breakfast LLC
Property entrance

3. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (116 reviews)
"Cute place. Antiquey Excellent breakfast!"
United States
Valerie
The price is CA $194
CA $215 total
includes taxes & fees
Sep 7 - Sep 8
Truman Gillet House Bed & Breakfast
Garden

4. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (13 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is CA $181
CA $287 total
includes taxes & fees
Sep 7 - Sep 8
Sunny Peace Homestay
Interior detail

5. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (62 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $256
CA $286 total
includes taxes & fees
Sep 13 - Sep 14
Wilder House Berkshires
Exterior

6. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,001 reviews)
"Quaint Inn in a scienic location."
United States
Brian
The price is CA $308
CA $379 total
includes taxes & fees
Sep 13 - Sep 14
Simsbury 1820 House
Exterior detail

7. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
8.0 out of 10, Very good, (5 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 CA $191
CA $247 total
includes taxes & fees
Sep 7 - Sep 8
Peaceful Modern Private Room with Comfort & Charm
Front of property

8. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (140 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is CA $423
CA $470 total
includes taxes & fees
Sep 22 - Sep 23
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"The Farmington Inn is charming, comfortable and quiet, with an excellent location and easy access to all that CT has to offer."
Rachael Gagner 7-night trip
Posted less than an hour ago
The Farmington Inn & Suites

Find out more about Winchester

Winchester B&B information

Number of reviews
1,659
Accommodation
11 B&B
Lowest Price
CA $167
Highest Price
CA $470

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. Locust Tree Bed and Breakfast LLC: 7 rooms. 11.5 mi (18.5 km) from the downtown core. 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. Sunny Peace Homestay: 2 rooms. 13.2 mi (21.2 km) from the heart of downtown. Enjoy the outdoor pool and unique décor. Wilder House Berkshires: 5 rooms. Located 17.2 mi (27.7 km) from the core of Winchester. Enjoy the free cooked 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 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?
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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