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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Winchester holiday rentals

Interior

•Charming One-Level Home • Feels Like Home

•Charming One-Level Home • Feels Like Home
Menifee
The price is HK$2,860
HK$4,380 total
includes taxes & fees
24 Jun - 25 Jun
•Charming One-Level Home • Feels Like Home
Property grounds

A Cozy Sunrise Glamping Escape with Panoramic View

A Cozy Sunrise Glamping Escape with Panoramic View
Fallbrook
The price is HK$823
HK$1,299 total
includes taxes & fees
16 Jun - 17 Jun
A Cozy Sunrise Glamping Escape with Panoramic View
Property grounds

The Pony Experience Farm Stay! 501c3

The Pony Experience Farm Stay! 501c3
Valle De Los Caballos
9.0 out of 10, Wonderful, (7 reviews)
"Great experience at Namaste Farms! The camper was cozy and we loved being able to walk around and visit all the animals. Location is a farm but very close to multiple vineyards and town so it was a perfect getaway."
United States
Jennifer
The price is HK$1,959
HK$2,500 total
includes taxes & fees
25 Jun - 26 Jun
The Pony Experience Farm Stay! 501c3
Exterior

Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
9.4 out of 10, Exceptional, (6 reviews)
"I happened to receive a complimentary upgrade during my visit, and it added a special touch to my stay. The cabin itself was wonderful and Cayla at Idyllwild Realty was great! The cabin was a perfect getaway and walking distance to town."
United States
Heather
The price is HK$1,011
HK$1,112 total
includes taxes & fees
15 Jun - 16 Jun
Idyllwild Realty Vacations
Outdoor spa tub

Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
10.0 out of 10, Exceptional, (26 reviews)
"Wonderful stay. Beautiful space, great hospitality and perfect tiny home. We thoroughly enjoyed our stay."
United States
Zachary
The price is HK$1,553
HK$2,187 total
includes taxes & fees
25 Jun - 26 Jun
Coral Tree House
Property grounds

Entire cozy two floor guest house located in rainbow near Temecula

Entire cozy two floor guest house located in rainbow near Temecula
Fallbrook
10.0 out of 10, Exceptional, (2 reviews)
"Nice place cozy place definitely recommend!"
United States
Jayden B.
The price is HK$866
HK$1,023 total
includes taxes & fees
14 Jun - 15 Jun
Entire cozy two floor guest house located in rainbow near Temecula
Terrace/patio

Private 1-Bedroom Suite at Eagle Creek

Private 1-Bedroom Suite at Eagle Creek
Idyllwild-Pine Cove
The price is HK$1,293
HK$2,124 total
includes taxes & fees
3 Jul - 4 Jul
Private 1-Bedroom Suite at Eagle Creek
3 outdoor pools, pool umbrellas, pool loungers

The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.2 out of 10, Wonderful, (98 reviews)
"This place is great!"
United States
Amanda
The price is HK$1,183
HK$1,391 total
includes taxes & fees
14 Jun - 15 Jun
The Cottages at Golden Village Palms RV Resort
Exterior

Cozy cabin retreat nestled among forest trees

Cozy cabin retreat nestled among forest trees
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (10 reviews)
"We absolutely loved our stay at this clean, cozy cabin. The hosts really went above and beyond to make sure the home is well stocked and comfortable, We are already looking forward to visiting again. "
United States
KIM
The price is HK$1,262
HK$2,626 total
includes taxes & fees
16 Jun - 17 Jun
Cozy cabin retreat nestled among forest trees
Exterior

Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property

Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Menifee
10.0 out of 10, Exceptional, (3 reviews)
"The host was very welcoming. "
United States
Linda L.
The price is HK$776
HK$1,089 total
includes taxes & fees
15 Jun - 16 Jun
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Terrace/patio

The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe

The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe
Idyllwild-Pine Cove
9.8 out of 10, Exceptional, (25 reviews)
"Had a great time! "
United States
Jimmy S
The price is HK$1,199
HK$3,109 total
includes taxes & fees
14 Jun - 15 Jun
The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe
TV, fireplace, ping pong, stereo

"Rustic Elegance - A Woodland Escape"

"Rustic Elegance - A Woodland Escape"
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (25 reviews)
"This property is so pretty! It is tucked away in a nice quiet neighborhood. The cabin is well stocked with basic necessities, clean, and is just beautiful. Plus it is pet friendly which we needed. Mark was very attentive during the booking and check in process. We will definitely be staying again when we visit Idyllwild. Highly recommend!!"
United States
Ramona M.
The price is HK$1,246
HK$4,442 total
includes taxes & fees
21 Jun - 22 Jun
"Rustic Elegance - A Woodland Escape"
Property grounds

Dog-friendly mountain home with amazing views - near town & hiking

Dog-friendly mountain home with amazing views - near town & hiking
Idyllwild
8.6 out of 10, Excellent, (140 reviews)
"House was great! Cozy, and welcoming. They had music and lights on and everything was spotless and perfect. Jacuzzi out back was hot and ready to go, and the fireplace was a perfect touch for the cold winter night!"
United States
Joel M.
The price is HK$928
HK$2,434 total
includes taxes & fees
15 Jun - 16 Jun
Dog-friendly mountain home with amazing views - near town & hiking
Exterior

Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown

Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely beautiful cabin. "
United States
Colleen D.
The price is HK$1,206
HK$2,949 total
includes taxes & fees
21 Jun - 22 Jun
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Interior

Twin Rock Tree House - Vintage Cabin

Twin Rock Tree House - Vintage Cabin
Idyllwild-Pine Cove
9.8 out of 10, Exceptional, (35 reviews)
"Cozy cabin. "
United States
Arpa S.
The price is HK$1,175
HK$2,230 total
includes taxes & fees
29 Jun - 30 Jun
Twin Rock Tree House - Vintage Cabin
Interior

Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is HK$1,003
HK$2,282 total
includes taxes & fees
12 Jul - 13 Jul
Hike, Sip & Explore: Couples Retreat in Fallbrook
Smart TV, fireplace

Hobbit House - Heart of Town - Stunning Remodel

Hobbit House - Heart of Town - Stunning Remodel
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (28 reviews)
"Amazing cabin!"
United States
Chris R.
The price is HK$1,215
HK$4,431 total
includes taxes & fees
27 Jun - 28 Jun
Hobbit House - Heart of Town - Stunning Remodel
Interior

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Idyllwild-Pine Cove
9.8 out of 10, Exceptional, (25 reviews)
"Very clean, I enjoyed the stay very quiet surroundings. "
United States
Sofia
The price is HK$1,051
HK$2,218 total
includes taxes & fees
21 Jun - 22 Jun
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Property grounds

Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record

Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (9 reviews)
"Lovely and quiet cabin. Thoughtful touches throughout. We loved building a fire and relaxing in the loft. "
United States
Emily K.
The price is HK$940
HK$2,226 total
includes taxes & fees
17 Jun - 18 Jun
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
Property grounds

Cactus Garden Cottage…Best Location!!

Cactus Garden Cottage…Best Location!!
Fallbrook
10.0 out of 10, Exceptional, (67 reviews)
"Loved the location and garden"
United States
Cyrus
The price is HK$979
HK$1,677 total
includes taxes & fees
21 Jun - 22 Jun
Cactus Garden Cottage…Best Location!!
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

Hotel Xola

Hotel Xola

8/10 Good
"Staff at the hotel was great. You could tell the property was older and a few things didn’t work. The microwave in my room didn’t work, the jets in the hot tub didnt work. There were knicks in the wall that weren’t patched. The place could use a little love and some work. The carts to help with you baggage were coming apart. Hopefully ownership sees this and invests a little love into the place but the room was nice and spacious and the furniture seemed upgraded. I would stay here again but would love the hot tub to be fixed so my achy bones can feel rejuvenated."
Stephen 1-night trip
Posted less than an hour ago
Hotel Xola

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its wineries and coffee shops. Make sure you have time to check out the bars while you're in the area.

What are some of the best holiday rentals that Winchester has to offer?

Idyllwild Realty Vacations: This holiday home rental outside Winchester comes with WiFi so that you can feel at home during your trip. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Winchester are 1 Bed Room Casita-Suite with Private Entrance and 5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!.

How many holiday rentals will I find in Winchester?

Choose from 35 Expedia holiday rentals in Winchester for a memorable holiday.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Western Science Center, or get out into nature at a spot like Lake Perris. K1 Circuit and Pechanga Resort & Casino are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.