Winchester Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Winchester

Outdoor dining
1 Bed Room Casita-Suite with Private Entrance

Holiday Home in Winchester

9.8 out of 10, Exceptional, (59)
"Very nice property"
United States
Dillon T.
The price is HK$406
HK$1,031 total
includes taxes & fees
10 Dec - 11 Dec
1 Bed Room Casita-Suite with Private Entrance
Outdoor pool
Coral Tree House

Cabin in Fallbrook

3.0 star property
10.0 out of 10, Exceptional, (22)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is HK$1,002
HK$1,589 total
includes taxes & fees
7 Dec - 8 Dec
Coral Tree House
Individually decorated, individually furnished, desk, laptop workspace
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Aparthotel in Moreno Valley

3.0 star property
9.8 out of 10, Exceptional, (23)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is HK$898
HK$1,064 total
includes taxes & fees
13 Dec - 14 Dec
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3 outdoor pools, pool umbrellas, pool loungers
The Cottages at Golden Village Palms RV Resort

Cottage in Hemet

3.0 star property
9.4 out of 10, Exceptional, (78)
"Amazing stay, will visit again"
United States
Miguel
The price is HK$1,175
HK$1,382 total
includes taxes & fees
7 Dec - 8 Dec
The Cottages at Golden Village Palms RV Resort
Exterior
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!

Cabin in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (40)
"just a quick one night stay- it was great"
United States
Rick M.
The price is HK$840
HK$1,825 total
includes taxes & fees
10 Dec - 11 Dec
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Property grounds
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

Cabin in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (6)
"Very clean, I enjoyed the stay very quiet surroundings. "
United States
Sofia
The price is HK$803
HK$1,900 total
includes taxes & fees
9 Dec - 10 Dec
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Property grounds
Secluded mystical cabin in Idyllwild-Pine Cove

Cabin in Idyllwild-Pine Cove

9.0 out of 10, Wonderful, (13)
"Nice rustic cabin close to town but secluded. "
United States
Jacob H.
The price is HK$490
HK$1,230 total
includes taxes & fees
7 Dec - 8 Dec
Secluded mystical cabin in Idyllwild-Pine Cove
Exterior
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown

Cabin in Idyllwild-Pine Cove

2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was great! Cabin was great! Couldn't recommend more!"
United States
Daniel L.
The price is HK$1,114
HK$2,798 total
includes taxes & fees
11 Dec - 12 Dec
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Property grounds
Cactus Garden Cottage…Best Location!!

Cottage in Fallbrook

10.0 out of 10, Exceptional, (52)
"Charming little place perfect for a couple of nights. Lots of natural light, easy parking, and very quiet. "
United States
Heather M.
The price is HK$895
HK$1,464 total
includes taxes & fees
29 Dec - 30 Dec
Cactus Garden Cottage…Best Location!!
Smart TV
3RV/ parking/Netflix/ private/excellent location

Mobile Home in Moreno Valley

8.6 out of 10, Excellent, (8)
"Very clean Owners were very sweet and helpful. "
United States
erika
The price is HK$381
HK$965 total
includes taxes & fees
7 Dec - 8 Dec
3RV/ parking/Netflix/ private/excellent location
Exterior
Cozy cabin retreat nestled among forest trees

Cabin in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (3)
"We took a last minute escape to Idyllwild and found this cabin! It was so cozy! We loved it and already are planning a trip to come back! Thank you for hosting us we had an amazing time!"
United States
wendy c.
The price is HK$1,004
HK$2,249 total
includes taxes & fees
8 Dec - 9 Dec
Cozy cabin retreat nestled among forest trees
Fridge, microwave, oven, stovetop
Lakeside Escape, Cozy Getaway

Holiday Home in Lake Elsinore

2.0 star property
The price is HK$679
HK$1,107 total
includes taxes & fees
9 Dec - 10 Dec
Lakeside Escape, Cozy Getaway
Terrace/patio
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record

Apartment in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (6)
"It was the perfect escape from fireworks as my dog gets very anxious. It was very relaxing to be there."
United States
Brianna J.
The price is HK$841
HK$1,984 total
includes taxes & fees
7 Dec - 8 Dec
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
Exterior
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!

Cabin in Idyllwild-Pine Cove

9.8 out of 10, Exceptional, (27)
"We stayed there the whole trip. Never even went into town. The property has great amenities and we brought our food and cooked easily. Traeger gril is a definite plus! Would book it again."
United States
david W.
The price is HK$965
HK$2,518 total
includes taxes & fees
11 Dec - 12 Dec
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Outdoor dining
Tiny Cabin With Additional Open Air Sleeping Porch

Cabin in Rainbow

10.0 out of 10, Exceptional, (21)
"Fun little property with very attentive hosts. They obviously have worked hard to create a magical hideaway and they love sharing it with their guests."
United States
Debra E.
The price is HK$1,012
HK$1,918 total
includes taxes & fees
7 Dec - 8 Dec
Tiny Cabin With Additional Open Air Sleeping Porch
Fridge, microwave, oven, stovetop
Peach Blossom Country House

Holiday Home in Hemet

9.2 out of 10, Wonderful, (5)
"Communication with property host was very good. "
United States
Ken R.
The price is HK$1,296
HK$2,651 total
includes taxes & fees
10 Dec - 11 Dec
Peach Blossom Country House
Outdoor spa tub
Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK

Cabin in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (6)
"We had a last minute vacation and couldn’t have asked for a better place. Just what we needed to unwind. Loved every moment of our stay and are already talking about returning. Many thanks!"
United States
Evonne C.
The price is HK$856
HK$2,390 total
includes taxes & fees
10 Dec - 11 Dec
Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK
Outdoor spa tub
TheTiny Beach House at Coral Tree House

Cabin in Fallbrook

10.0 out of 10, Exceptional, (4)
"Amazing loved everything the property Can't wait to go back"
United States
Daniel D.
The price is HK$1,012
HK$1,918 total
includes taxes & fees
7 Dec - 8 Dec
TheTiny Beach House at Coral Tree House
2 bedrooms, Internet
Dog Friendly A-frame Hot Tub Nature Views

Apartment in Idyllwild

2.0 star property
Dog Friendly A-frame Hot Tub Nature Views
Terrace/patio
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler

Holiday Home in Menifee

10.0 out of 10, Exceptional, (12)
"Great place!"
United States
JoePiccoloh
The price is HK$771
HK$1,020 total
includes taxes & fees
4 Jan - 5 Jan 2026
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
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

Pala Casino Spa And Resort

Pala Casino Spa And Resort

10/10 Excellent
"Beautiful room, great food at a reasonable price and the overall place is wonderful. "
Linda 1-night trip
Posted 16 hours ago
Pala Casino Spa And Resort

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:

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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?

Exclusive Resort Style Estate in Temecula: This holiday home rental outside of Winchester is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 32 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 Orange Empire Railroad Museum, or get out into nature at a spot like Diamond Valley Lake Marina. 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.