An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Search Guest Houses in Winchester from CA $262

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Aug 28 - Aug 30
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Oct 16 - Oct 18

Our top choices for Winchester guest houses

Living area

1. Luxury on Main / North

Luxury on Main / North
Richmond
9.8 out of 10, Exceptional, (110 reviews)
"Andrew the host was awesome. Quick response on everything. The rental was absolutely beautiful. It is a great location to walk to downtown. Total gem!"
United States
Trent W.
The price is CA $141
CA $262 total
includes taxes & fees
Sep 20 - Sep 21
Luxury on Main / North
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 Manchester

The Manchester

10/10 Excellent
"We had a fantastic stay at the Manchester. The hotel is beautiful - the lobby had a nice energy and the rooftop bar was gorgeous. Our waiter was particularly great - very helpful and full of great recommendations for Lexington. The rooms were decorated thoughtfully and were very clean/comfortable. Best part - walking distance to the distillery area and free shuttle service at night to the city or anywhere else you want to go (we loved our driver Sam). We will definitely stay again - highly recommend!"
Kirstin 1-night trip
Posted less than an hour ago
The Manchester

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
110
Accommodation
2 Guest Houses
Lowest Price
CA $262
Highest Price
CA $262

Frequently asked questions

What are the most popular guest houses in Winchester according to reviews?
College Park Bungalow is a great choice for travellers seeking a cozy retreat in Winchester, offering a warm and friendly space. With convenient onsite parking and a well-equipped kitchen, it provides the superb setting for those who value quality and convenience. Guests have praised the bungalow for its thoughtful amenities, making it an ideal home base for exploring the charming surroundings of Winchester.
What is the nightly rate for a guest house in Winchester?
Rates for Winchester guest houses vary, but travelers can find great-value prices from CA $262 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winchester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Winchester guest house and a B&B?
A guest house in Winchester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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