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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Winchester bed & breakfast

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

1. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (243 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is AU$286
includes taxes & fees
2 Nov - 3 Nov
Blackberry River Inn
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

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, (452 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is AU$172
includes taxes & fees
30 Oct - 31 Oct
Locust Tree Bed and Breakfast LLC
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

3. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
8.8 out of 10, Excellent, (18 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$296
includes taxes & fees
3 Nov - 4 Nov
Sunny Peace Homestay
A house with a porch, American flags, and a pathway leading to a bench.

4. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (120 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is AU$221
includes taxes & fees
1 Nov - 2 Nov
Truman Gillet House Bed & Breakfast
A large, historic building with a covered porch and outdoor seating area.

5. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,001 reviews)
"Such a warm welcome from the wonderful woman at the desk, beautiful inn with a very comfortable bed and on site restaurant which is super convenient! Loved our stay!"
United States
Kimberly
The price is AU$304
includes taxes & fees
4 Nov - 5 Nov
Simsbury 1820 House
Interior detail

6. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is AU$261
includes taxes & fees
1 Nov - 2 Nov
Wilder House Berkshires
A building with a grey exterior, a front door, and a small porch with steps.

7. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
8.4 out of 10, Very good, (6 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$365
includes taxes & fees
3 Nov - 4 Nov
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"A beautiful inn in a beautiful town. Loved our stay and will definitely be back."
Kenneth 3-night trip
Posted 1 hour ago
The Farmington Inn & Suites

Find out more about Winchester

Winchester B&B information

Number of reviews
453
Accommodation
11 B&B
Lowest Price
AU$172
Highest Price
AU$365

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. Sunny Peace Homestay: 2 rooms. 13.2 mi (21.2 km) from the city centre. 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 The Marina at Highland Lake and Burr Pond 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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