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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 22 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 "
The price is SAR 274
SAR 419 total
includes taxes & fees
8 Mar - 9 Mar
Country Holiday House

Private bedroom in Desert Western House near Wine Country

2.0 star property
9.2 out of 10, Wonderful, (22)
"Cozy home and beds are exceptional customer service. Beds are super comfortable. "
The price is SAR 260
SAR 404 total
includes taxes & fees
8 Mar - 9 Mar
Private bedroom in Desert Western House near Wine Country

COZY PRIVATE STUDIO GUEST HOUSE

9.8 out of 10, Exceptional, (44)
"Quiet and cozy. Great amenities, everything you need for a relaxing stay."
The price is SAR 221
SAR 465 total
includes taxes & fees
25 Feb - 26 Feb
COZY PRIVATE STUDIO GUEST HOUSE

Temecula Wine Country Guest House w/Kitchen - Prime Location

10.0 out of 10, Exceptional, (75)
"We loved the little studio that we stayed at in Temecula. Nice and quiet in the place was very well set up for us. The bed is a little high off the ground, so I had to create a little step out of pillows to get into bed! Also, there is one road in that the road is smooth and great to drive on - if your GPS takes you a different way it’s a washboard road - very jarring! "
Temecula Wine Country Guest House w/Kitchen - Prime Location

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)

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

Vineyard Retreat-Private Guest home

10.0 out of 10, Exceptional, (10)
"This property is exactly as described. We went to a wedding across the street at the winery and this location was PERFECT! The owners are so sweet and are very accommodating. It was a nice surprise to meet them! Hostess with the mostess!! Highly recommend staying at this property. We will be back! "
Vineyard Retreat-Private Guest home

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 Mar - 11 Mar
Balloons and Wine

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

Large Custom Guest House On Hill Top Estate In Bonsall

9.6 out of 10, Exceptional, (103)
"The view is incredible, and at first glance the unit is charming. The bed is super comfortable. The water pressure in the shower was great. The owners/managers are kind, answer immediately and seem to genuinely want to please. But there are problems. There were dirty dishes in the cupboard and a cleaning rag left drying on the bathroom plunger. Toaster crumbs all over the cupboard. We really began to wonder what is actually clean in this unit. The owners are appropriately apologetic and...
Large Custom Guest House On Hill Top Estate In Bonsall

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

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

Newly Remodeled Wine-Country Retreat

9.8 out of 10, Exceptional, (9)
"Great quiet cottage in the foothills. Warm, inviting and private ADU. Gracious and attentive host - will stay again in the future! Very enjoyable and relaxing."
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

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

Vineyard Casita near Wineries and Galway Downs

Vineyard Casita near Wineries and Galway Downs

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.
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

Other property types in Winchester

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (38)
"This casita was the most perfect place for me to stay. The host, Elizabeth, sure packs a punch in the casita with everything you could possibly need. Relaxing, beautiful, quiet and safe. Elizabeth was very communicative before my arrival and during my stay. Very responsive. I would definitely stay here again, over and over. Thank you Elizabeth and VRBO for offering this casita. "
The price is SAR 218
SAR 502 total
includes taxes & fees
23 Feb - 24 Feb
1/Bed Room Casita-Suite with Private Entrance

Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

2.0 star property
8.0 out of 10, Very Good, (2)
"Firstly, the pictures do a great job of showing what the home has to offer and what it looks like. However, I was still impressed by the size of the property and all the offerings it had. All of my guests (around 20) greatly enjoyed all the amenities and have high praise, which to me is exactly what I hope for when hosting that many people. Probably one of my favorite features is the speaker system that covers a few main rooms and outside as well. It’s extremely convenient as a host to have full...
The price is SAR 3,675
SAR 6,892 total
includes taxes & fees
23 Feb - 24 Feb
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

Sip and Swim Just Minutes From Temecula's Wine Country

10.0 out of 10, Exceptional, (18)
"Loved it. Very easy to communicate with the owner. The backyard looks like a tropical oasis. Very easy checking in & out process. clean & roomy. Several board games to choose from. "
Sip and Swim Just Minutes From Temecula's Wine Country
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.