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Book Winchester Bed & Breakfast

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Compare B&B in Winchester with updated reviews, rates, and availability.

Other property types in Winchester

Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, 27 reviews
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
Charming Waterfront Log Cabin
Cozy 2-bedroom Unit with private backyard
Private kitchen | Fridge, microwave, oven, stovetop
Cozy 2-bedroom Unit with private backyard
10.0 out of 10, Exceptional, 11 reviews
"Very clean and neat if in the area again would definitely stay here again."
Cozy 2-bedroom Unit with private backyard
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Interior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, 5 reviews
"Copley Cottage was phenomenal! Our group included family from Los Angeles, Pa and NJ. We wanted to introduce our newest family member to great grandpa who lives in the area. We were impressed with the design and lay out of the house. . High end kitchen and open concept made for easy enjoyable time together. Waking up to the views of the lake and area felt like a bit of paradise. The private beach, dock and sauna were outstanding additions. Overall a stay that will be remembered forever"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
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.

Winchester B&B information

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 B&B
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Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your trip to Winchester. While you’re enjoying your trip to Winchester, Pisgah State Park and Rhododendron State Park are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel. Whether it’s a cozy reading space or a beautiful breakfast room, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Below are some well-liked B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester.Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the downtown core. Enjoy the local cuisine breakfast and library. Centennial House: 5 rooms. Situated 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.The One Cat B&B: 2 rooms. Located 10.3 mi (16.6 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
What's the best time of year to book my B&B in Winchester?
When you’re dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. 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 28°F. The snowiest months in Winchester are January, March, April, and February, with each month seeing an average of 11 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Birch Point and Pisgah State Park are some notable spots. You might put Rhododendron State Park and Ashuelot River on your list if you want to see more of the area.

Recent reviews of Winchester hotels
Expedia verified reviews

Black Mountain Inn

Black Mountain Inn

5/5 Excellent
"Very kind man at check in.. loved the kitty at the front desk! The man at check is was extremely friendly and helpful!"
A verified traveler from Philadelphia stayed at Black Mountain Inn
Posted 2 days ago
Black Mountain Inn