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Search Guest Houses in Winchester

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Check prices for these dates

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

Country Holiday House

2.0 star property
8.8 out of 10, Excellent, (28)
"Everything expected lovely home to stay "
Country Holiday House

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 404 total
includes taxes & fees
12 Apr - 13 Apr
Private bedroom in Desert Western House near Wine Country

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

9.8 out of 10, Exceptional, (202)
"What an incredible journey this was! I must emphasize the importance of following the owner's directions rather than relying on Google Maps or any other navigation tool. When we arrived, we initially followed Google Maps, which made our approach quite cumbersome. However, once we shifted to the owner's instructions, the experience became far more seamless.The casita was immaculate and exactly as advertised. You truly feel like you’re on top of the world at this property, overlooking the stunning...
The price is SAR 473
SAR 833 total
includes taxes & fees
31 Mar - 1 Apr
Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES!

COZY PRIVATE STUDIO GUEST HOUSE.

9.8 out of 10, Exceptional, (45)
"When visiting Menifee to see our grandbaby, we need a place to stay as her house is too small for overnight visitors. We don't usually spend a lot of time actually in the rental because we spend our days at their home. I found this Casita on VRBO and it was perfect! Small in size, every amenity was provided. It was immaculate, comfortable and stocked with snacks, water, a variety of coffee, personal care items and any random item you may have forgotten. We had a nice bed, extra pillows, Wifi and...
The price is SAR 308
SAR 551 total
includes taxes & fees
31 Mar - 1 Apr
COZY PRIVATE STUDIO GUEST HOUSE.

Beautiful Guest Cottage PERMITTED TEMECULA WINE COUNTRY VACATION HOME

9.6 out of 10, Exceptional, (29)
"Beautiful collage with vineyard views"
Beautiful Guest Cottage PERMITTED TEMECULA WINE COUNTRY VACATION HOME

Temecula Wine Country Guest House w/Kitchen - Prime Location

10.0 out of 10, Exceptional, (78)
"Loved the location and privacy!"
Temecula Wine Country Guest House w/Kitchen - Prime Location

Bella Casita-A Quiet Gem Near Wine Country

10.0 out of 10, Exceptional, (21)
"This was the first time I stayed at a vrbo and had everything I needed. I didn’t have to go buy oil or spices or pans/utensils to cook with, laundry detergent for the washer, and there was even coffee/sugar/creamer. They literally thought of everything! Other rental owners should take a lesson from Bella Casita. Thank you so much!"
Bella Casita-A Quiet Gem Near Wine Country

Balloons and Wine

4.0 star property
8.6 out of 10, Excellent, (7)
"The owner was very nice and it is obvious. She put a lot of effort into the rooms in the rooms. The first night was wonderful. The bedding was so comfortable. Everything was great. Bottom line, it is a shared situation. People arrived talking at 3/2 AM and continued to talk For over 30 minutes."
The price is SAR 392
SAR 443 total
includes taxes & fees
10 Apr - 11 Apr
Balloons and Wine

The Twin Cabs-Active Winery House

8.4 out of 10, Very Good, (17)
"My partner and I stayed here for a week before our wedding in Temecula. It was ths perfect combination of relaxation and convenience "
The Twin Cabs-Active Winery House

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

9.0 out of 10, Wonderful, (94)
"This was a studio cabin. It is located beside the host’s home. I needed to talk with him about the tv. I could not reach him so I knocked on his door. He was not home. I drove into town to get a connection. I have not had a response. I needed to turn the wifi off to use my devices. No tv not good wifi. Squeaky bed and broken hanging porch chairs mentioned in other reviews were not fixed. No instructions at all for air conditioner nor fireplace or using tv. No phone number was given for host. ....
The Banana Belt Bungalow (air-conditioning! - 4WD/AWD required)

Newly Remodeled Wine-Country Retreat

9.6 out of 10, Exceptional, (10)
"The property was spotless and cozy. It was just big enough for 4 of us, no more than 4, though, to sleep in this house. That web description is very accurate. The property manager is very responsive and kind. Always make sure to check in with you. The property is secluded, so you aren’t bothered by street noise. It’s nice to see the Milky Way at night because of the location. Also, it is not more than 15 mins from apart the ocean side, with plenty of dining options and stores. The absolute only...
Newly Remodeled Wine-Country Retreat

Fallbrook's Finest Hideaway Casa - Pool, Game Rm

10.0 out of 10, Exceptional, (5)
"Property was clean and updated. Great relaxing location. I will stay again!"
Fallbrook's Finest Hideaway Casa - Pool, Game Rm

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

10.0 out of 10, Exceptional, (37)
"This is a unique place nestled in the hills and mountains near Eucalyptus and Avocado trees. It is so natural and beautiful. I will be back."
Mountain Rim Retreat - Miles of Private Hiking & Biking Trails - Endless Views

Scenic De Luz Guest Suite

10.0 out of 10, Exceptional, (3)
"Great place in great Temecula location."
Scenic De Luz Guest Suite

Golf courses, Wineries, beaches

10.0 out of 10, Exceptional, (32)
"We just loved! staying at the beautiful “touch of Tuscany” hilltop location! Private parking and entrance and view over the town of Fallbrook and surrounding mountains. The host Paul and his wife were very friendly and communicative. Kitchen is well equipped with full size refrigerator and stove. Was "
Golf courses, Wineries, beaches

WELCOME TO THE BEAUTIFUL CASITA DEL CIELO.

10.0 out of 10, Exceptional, (14)
"A beautiful Casita and the views are spectacular. They have done such a great job with decorating, stocking and landscaping. The care they have put into all the succulent plants adds so much beauty and interest. We loved the deck on all the sides and furnished and decorated for you comfort. Bianca is so hospitable, we arrived and there was fresh croissants with butter and jam waiting under a glass cover and fresh fruit that we had to pinch to see if it was real. I never imagined being treated so...
WELCOME TO THE BEAUTIFUL CASITA DEL CIELO.

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!"
Retro Ranch Cottage 800sf Pool HotTub Pickleball

Magic Villas

3.0 star property
Magic Villas

Spacious Retreat w/ Private Entrance

10.0 out of 10, Exceptional, (4)
"This rental was exactly what I needed for my stay in the area! The neighborhood is safe and secure. The unit was a perfect place to relax at the end of some stressful days. The property owners were accommodating and responded quickly to messages. If I come back to the area, I will checking the availability here before anywhere else. Very convenient to anything a person could need! Enjoyed my stay very much!"
Spacious Retreat w/ Private Entrance

Genesis Guest House

4.0 star property
Genesis Guest House
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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Other property types in Winchester

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (38)
"The house itself is lovely—well-kept, nicely furnished, and comfortable for a group. Unfortunately, there was a fairly large leak in the living room due to heavy rain right as we checked in. That said, the homeowner responded quickly and handled it to our satisfaction.A couple things to keep in mind: the bunk room doesn’t have a nearby bathroom, so anyone staying there will need to go through another bedroom to shower. It’s manageable, just not the most convenient setup.We also received a...
Chateau Vino - French Style Chalet

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (18)
"This was by far one of the best places I've stayed. Everything was exceptional! Little touches like water bottles, toothbrushes (in case you forgot yours) to cereal, coffee, real cream, wine and other goodies. The pool and hot tub were beautiful and easy to turn on. Fun games and plenty of room for the 6 of us on a girl's wine tasting birthday weekend. Highly, highly recommend. Beds were very comfortable (pillows were a little hard so if you want soft pillows you might want to bring your own)...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

Wine Country Resort - Close to Wineries

Wine Country Resort - Close to 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.