Photo by Betsy Wood

Search Guest Houses in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
16 Jum. I - 18 Jum. I
In two weeks
23 Jum. I - 25 Jum. I
In one month
6 Jum. II - 8 Jum. II
In two months
4 Raj. - 6 Raj.

Compare 30 Guest Houses in Winchester with updated reviews, rates, and availability.

Country Holiday House
Living area

Country Holiday House

2.0 star property
9.0 out of 10, Wonderful, (31)
"Love staying here "
Country Holiday House
Private bedroom in Desert Western House near Wine Country
Living area

Private bedroom in Desert Western House near Wine Country

2.0 star property
9.4 out of 10, Exceptional, (24)
"Place was amazing "
The price is SAR 260
SAR 423 total
includes taxes & fees
20 May - 21 May
Private bedroom in Desert Western House near Wine Country
Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!
Exterior detail

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

9.8 out of 10, Exceptional, (206)
"Beautiful property"
The price is SAR 473
SAR 814 total
includes taxes & fees
10 May - 11 May
Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!
COZY PRIVATE STUDIO GUEST HOUSE.
Exterior

COZY PRIVATE STUDIO GUEST HOUSE.

9.8 out of 10, Exceptional, (48)
"Quiet and cozy. Great amenities, everything you need for a relaxing stay."
The price is SAR 263
SAR 506 total
includes taxes & fees
19 May - 20 May
COZY PRIVATE STUDIO GUEST HOUSE.
Beautiful Guest Cottage PERMITTED TEMECULA WINE COUNTRY VACATION HOME
Aerial view

Beautiful Guest Cottage PERMITTED TEMECULA WINE COUNTRY VACATION HOME

9.6 out of 10, Exceptional, (29)
"We thoroughly enjoyed our stay. The rooms were great. And the scenery was fantastic."
Beautiful Guest Cottage PERMITTED TEMECULA WINE COUNTRY VACATION HOME
Large Custom Guest House On Hill Top Estate In Bonsall
Outdoor dining

Large Custom Guest House On Hill Top Estate In Bonsall

9.6 out of 10, Exceptional, (104)
"Place was beautiful and had all the amenities you could possibly need. We loved having coffee on the deck every morning and even brought our dogs as well as they loved the quiet and paths to take walks on. We will be staying here every time we come to visit family! Highly recommend!"
Large Custom Guest House On Hill Top Estate In Bonsall
Temecula Wine Country Guest House w/Kitchen - Prime Location
Outdoor pool

Temecula Wine Country Guest House w/Kitchen - Prime Location

10.0 out of 10, Exceptional, (79)
"nice quiet place close to all the wineries, "
Temecula Wine Country Guest House w/Kitchen - Prime Location
Bella Casita-A Quiet Gem Near Wine Country
Outdoor pool

Bella Casita-A Quiet Gem Near Wine Country

10.0 out of 10, Exceptional, (22)
"Quiet and accomidating."
Bella Casita-A Quiet Gem Near Wine Country
Balloons and Wine
Full-size fridge, microwave, oven, stovetop

Balloons and Wine

4.0 star property
8.8 out of 10, Excellent, (9)
"Very comfortable and relaxing overnight stay, just what we needed after spending a whole day visiting wineries. "
The price is SAR 392
SAR 443 total
includes taxes & fees
19 May - 20 May
Balloons and Wine
The Twin Cabs-Active Winery House
Outdoor pool

The Twin Cabs-Active Winery House

8.4 out of 10, Very Good, (17)
"A nice place for take a break from our trip around us "
The Twin Cabs-Active Winery House
The Banana Belt Bungalow (air-conditioning! - 4WD/AWD required)
1 bedroom, free WiFi, bed sheets

The Banana Belt Bungalow (air-conditioning! - 4WD/AWD required)

9.0 out of 10, Wonderful, (94)
"Overall everything was great!"
The Banana Belt Bungalow (air-conditioning! - 4WD/AWD required)
Newly Remodeled Wine-Country Retreat
Fridge, microwave, oven, stovetop

Newly Remodeled Wine-Country Retreat

9.6 out of 10, Exceptional, (10)
"Wonderful stay everything was as advertised!"
Newly Remodeled Wine-Country Retreat
Fallbrook's Finest Hideaway Casa - Pool, Game Rm
Outdoor dining

Fallbrook's Finest Hideaway Casa - Pool, Game Rm

10.0 out of 10, Exceptional, (6)
"Property was clean and updated. Great relaxing location. I will stay again!"
The price is SAR 911
SAR 1,947 total
includes taxes & fees
31 May - 1 Jun
Fallbrook's Finest Hideaway Casa - Pool, Game Rm
Mountain Rim Retreat - Miles of Private Hiking & Biking Trails - Endless Views
Outdoor pool

Mountain Rim Retreat - Miles of Private Hiking & Biking Trails - Endless Views

10.0 out of 10, Exceptional, (37)
"Wine and sunsets. Amazing location!"
Mountain Rim Retreat - Miles of Private Hiking & Biking Trails - Endless Views
Scenic De Luz Guest Suite
Outdoor dining

Scenic De Luz Guest Suite

10.0 out of 10, Exceptional, (4)
"Great place in great Temecula location."
Scenic De Luz Guest Suite
Golf courses, Wineries, beaches
Terrace/patio

Golf courses, Wineries, beaches

10.0 out of 10, Exceptional, (32)
"Very well thought out property. Very comfortable & great amenities & outdoor area."
Golf courses, Wineries, beaches
WELCOME TO THE BEAUTIFUL CASITA DEL CIELO.
Fridge, microwave, oven, stovetop

WELCOME TO THE BEAUTIFUL CASITA DEL CIELO.

10.0 out of 10, Exceptional, (14)
"We had a wonderful time during our month stay. The hosts have all the details covered. The property has great amenities and Bianca and Jiamez were so warm and welcoming. I would recommend this property to anyone traveling to the Fallbrook area."
WELCOME TO THE BEAUTIFUL CASITA DEL CIELO.
Retro Ranch Cottage 800sf Pool HotTub Pickleball
Pool

Retro Ranch Cottage 800sf Pool HotTub Pickleball

9.0 out of 10, Wonderful, (2)
"This cottage was amazing! Not only was it super clean but the decor was great and host was awesome! Very attentive and accommodating with any requests. The pool and outdoor area beautiful and everyone enjoyed there stay. We would definitely book another stay!"
The price is SAR 814
SAR 1,915 total
includes taxes & fees
7 May - 8 May
Retro Ranch Cottage 800sf Pool HotTub Pickleball
Magic Villas
Property grounds

Magic Villas

3.0 star property
Magic Villas
Spacious Retreat w/ Private Entrance
Fridge, microwave, coffee/tea maker, toaster

Spacious Retreat w/ Private Entrance

10.0 out of 10, Exceptional, (4)
"Beautiful, private casita. Super clean, quiet, and comfortable!"
Spacious Retreat w/ Private Entrance
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

1 Bed Room Casita-Suite with Private Entrance
Outdoor pool

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (40)
"Very nice neighborhood and close to shopping. Host is very communicative."
The price is SAR 218
SAR 502 total
includes taxes & fees
7 May - 8 May
1 Bed Room Casita-Suite with Private Entrance
Sip and Swim Just Minutes From Temecula's Wine Country
A heated pool

Sip and Swim Just Minutes From Temecula's Wine Country

9.8 out of 10, Exceptional, (20)
"It was a great home, enjoyed our stay!"
Sip and Swim Just Minutes From Temecula's Wine Country
Chateau Vino - French Style Chalet
Exterior

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (41)
"We booked Chateau Vino to celebrate my mom’s 90th birthday. We wanted a home that fit our whole family comfortably. The house is amazing and having space to relax, eat, and enjoy the outdoors with seating for all was perfect. We had a wonderful time and hope to return again. "
Chateau Vino - French Style Chalet
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.