An aerial view of a densely populated urban area with a river, surrounding mountains, and a clear sky.

Search Guest Houses in Winchester from CA $125

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Winchester guest houses

Front of property

1. Private bedroom in Peach Blossom Country House

Private bedroom in Peach Blossom Country House
2.0 star property
Hemet
9.2 out of 10, Wonderful, (53 reviews)
"Hotel was nice and staff treated us nice "
United States
beryl
The price is CA $62
CA $125 total
includes taxes & fees
Sep 1 - Sep 2
Private bedroom in Peach Blossom Country House
Living area

2. Private bedroom in Western Horizon Home

Private bedroom in Western Horizon Home
2.0 star property
Hemet
9.2 out of 10, Wonderful, (38 reviews)
"It was easy to find and the host was very organized and gave great instructions."
United States
Ayesha
The price is CA $69
CA $134 total
includes taxes & fees
Sep 2 - Sep 3
Private bedroom in Western Horizon Home
House

3. Balloons and Wine

Balloons and Wine
4.0 star property
Murrieta
8.0 out of 10, Very good, (26 reviews)
"Great hostess! Clean and so peaceful "
United States
Erika
The price is CA $145
CA $164 total
includes taxes & fees
Sep 3 - Sep 4
Balloons and Wine
Exterior

4. COZY PRIVATE STUDIO GUEST HOUSE.

COZY PRIVATE STUDIO GUEST HOUSE.
Sun City
10.0 out of 10, Exceptional, (69 reviews)
"Stayed 3/8-17 great host and hostess every thing was perfect felt the warmth and kindness! "
United States
JOYCE C.
The price is CA $74
CA $178 total
includes taxes & fees
Sep 2 - Sep 3
COZY PRIVATE STUDIO GUEST HOUSE.
Exterior

5. The New Inn

The New Inn
4.0 star property
Valle De Los Caballos
10.0 out of 10, Exceptional, (149 reviews)
"Always a wonderful stay with a tasty breakfast."
United States
Latasha
The price is CA $370
CA $414 total
includes taxes & fees
Sep 2 - Sep 3
The New Inn
Exterior detail

6. Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!

Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!
Temecula
9.8 out of 10, Exceptional, (245 reviews)
"Excellent atmosphere "
United States
Frank
The price is CA $175
CA $305 total
includes taxes & fees
Sep 7 - Sep 8
Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Tahquitz Pines Retreat

Tahquitz Pines Retreat

10/10 Excellent
"It’s our second time staying here and it was peaceful and relaxing as always. The office staff is wonderful and so friendly. We can’t wait to come back!"
Marisol 1-night trip
Posted 11 hours ago
Tahquitz Pines Retreat

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
580
Accommodation
23 Guest Houses
Lowest Price
CA $125
Highest Price
CA $414

Frequently asked questions

What are the most popular guest houses in Winchester according to reviews?
Retro Ranch Cottage is a delightful option for travellers visiting Winchester, offering a unique blend of comfort and adventure in a cozy 800-square-foot space. With a well-rounded 9.0 rating, this charming cottage features a fully equipped kitchen that invites you to whip up home-cooked meals, superb for families or groups looking for a convenient stay. The inviting garden creates a serene atmosphere where guests can unwind, while amenities like a sofa bed and studio layout add flexibility for larger families or groups.
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 $125 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.

Explore a world of travel with Expedia