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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

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, (217 reviews)
"The Inn is lovely and charming - and the breakfast was especially great."
United States
Rachel
The price is AU$220
includes taxes & fees
10 Sept - 11 Sept
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 AU$167
includes taxes & fees
11 Sept - 12 Sept
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, (117 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is AU$215
includes taxes & fees
20 Sept - 21 Sept
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 AU$288
includes taxes & fees
16 Sept - 17 Sept
Sunny Peace Homestay
Interior detail

5. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (63 reviews)
"Perfect little b&b."
United States
Mark
The price is AU$292
includes taxes & fees
16 Sept - 17 Sept
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 AU$325
includes taxes & fees
14 Sept - 15 Sept
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)
The price is AU$250
includes taxes & fees
21 Sept - 22 Sept
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 AU$470
includes taxes & fees
29 Sept - 30 Sept
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Clean room"
Mark Anthony 1-night trip
Posted 7 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Winchester B&B information

Number of reviews
1,994
Accommodation
11 B&B
Lowest Price
AU$167
Highest Price
AU$470

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. 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. Sunny Peace Homestay: 2 rooms. 13.2 mi (21.2 km) from the city centre. Enjoy the outdoor pool and unique decor. Wilder House Berkshires: 5 rooms. Located 17.2 mi (27.7 km) from the core of Winchester. Enjoy the free cooked 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.

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