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Search Guest Houses in Winchester from CA $129

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Check prices for these dates

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Aug 29 - Aug 31
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Browse Select Winchester Guest Houses

Luxury on Main / North
Outdoor dining

Luxury on Main / North

9.8 out of 10, Exceptional, (103)
"Great stay, will be back again!"
The price is CA $129
CA $249 total
includes taxes & fees
Aug 24 - Aug 25
Luxury on Main / North
College Park Bungalow
Outdoor dining

College Park Bungalow

College Park Bungalow
"The Guest House", Located on a 300 acre horse farm.
Pool

"The Guest House", Located on a 300 acre horse farm.

10.0 out of 10, Exceptional, (15)
"We could not have had a better experience with this stay! The property is beautiful and the home was very clean. And Teresa was an incredible host! Would recommend to anyone staying in the area."
"The Guest House", Located on a 300 acre horse farm.
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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent
"Hotel staff was friendly, room was clean and updated. Bathroom was spacious, with a very nice shower. "
Crystal 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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 $129 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.