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 $238

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Our top choices for Winchester guest houses

Smart TV, fireplace

Luxury on Main / North

Luxury on Main / North
Richmond
9.8 out of 10, Exceptional, (108 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 $117
CA $238 total
includes taxes & fees
Jun 24 - Jun 25
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

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

8/10 Good
"Staff was excellent and the breakfast and bar were nice. The only downside was the hotel having no heat"
Calvin 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Lexington/UK Coldstream

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
108
Accommodation
3 Guest Houses
Lowest Price
CA $238
Highest Price
CA $238

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 $238 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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