Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchester holiday rentals

Outdoor pool

Holiday Home in Winchester

1 Bed Room Casita-Suite with Private Entrance
9.8 out of 10, Exceptional, (66 reviews)
"It was an absolute dream to stay at this location. It was clean and very welcoming, and the host was very kind and had fantastic communication"
United States
Ryan
The price is HK$408
HK$1,036 total
includes taxes & fees
9 Mar - 10 Mar
1 Bed Room Casita-Suite with Private Entrance
Outdoor spa tub

Cabin in Fallbrook

Coral Tree House
3.0 star property
10.0 out of 10, Exceptional, (22 reviews)
"Michelle is very friendly and responsive. The room is beautiful. We really enjoyed our stay "
United States
Huaming
The price is HK$1,234
HK$1,842 total
includes taxes & fees
19 Mar - 20 Mar
Coral Tree House
Iron/ironing board, free WiFi

Holiday Home in Idyllwild

Idyllwild Realty Vacations
3.5 star property
10.0 out of 10, Exceptional, (1 review)
"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$1,049
HK$1,153 total
includes taxes & fees
19 Mar - 20 Mar
Idyllwild Realty Vacations
3 outdoor pools, pool umbrellas, pool loungers

Cottage in Hemet

The Cottages at Golden Village Palms RV Resort
3.0 star property
9.2 out of 10, Wonderful, (86 reviews)
"Amazing stay, will visit again"
United States
Miguel
The price is HK$1,181
HK$1,388 total
includes taxes & fees
9 Mar - 10 Mar
The Cottages at Golden Village Palms RV Resort
Individually decorated, individually furnished, desk, laptop workspace

Aparthotel in Moreno Valley

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
9.8 out of 10, Exceptional, (23 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is HK$889
HK$1,053 total
includes taxes & fees
7 Apr - 8 Apr
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
Terrace/patio

Cabin in Fallbrook

The New Way cabin: off-grid tiny cabin with ocean and mountain views.
10.0 out of 10, Exceptional, (11 reviews)
"A clean, serene environment conducive to mental reset"
United States
Shiella Mae
The price is HK$1,049
HK$1,400 total
includes taxes & fees
9 Mar - 10 Mar
The New Way cabin: off-grid tiny cabin with ocean and mountain views.
Terrace/patio

Cottage in GlenOak Hills

Romantic, private and surrounded by best Wineries!
10.0 out of 10, Exceptional, (21 reviews)
"The relaxing hot tub and views were great! Even saw some red-tailed hawks on the property. Close to some amazing wineries. Perfect for a couples getaway. Definitely planning on staying again in the future!"
United States
Rory H.
The price is HK$1,752
HK$3,082 total
includes taxes & fees
9 Mar - 10 Mar
Romantic, private and surrounded by best Wineries!
Interior

Apartment in Wildomar

Family Getaway w/ Pool, 8 Mi to Lake Elsinore!
3.0 star property
The price is HK$1,244
HK$2,636 total
includes taxes & fees
8 Mar - 9 Mar
Family Getaway w/ Pool, 8 Mi to Lake Elsinore!
Property grounds

Cabin in Idyllwild-Pine Cove

Cozy cabin retreat nestled among forest trees
10.0 out of 10, Exceptional, (7 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$1,267
HK$2,638 total
includes taxes & fees
9 Mar - 10 Mar
Cozy cabin retreat nestled among forest trees
Terrace/patio

Villa in GlenOak Hills

Amazing Views Villa with Spa / Close to Winery
8.6 out of 10, Excellent, (12 reviews)
"Beautiful property with amazing views! "
United States
Esther O.
The price is HK$3,230
HK$8,419 total
includes taxes & fees
10 Mar - 11 Mar
Amazing Views Villa with Spa / Close to Winery
2 bedrooms, free WiFi, bed sheets

Apartment in Idyllwild

Tiny Mountain Cabin under the pines. Close to town. Dogs ok.
9.8 out of 10, Exceptional, (45 reviews)
"Cabin was very clean and everything we would need was there. Area was quiet and relaxing. Enjoyed our stay very much."
United States
Sandy N.
Tiny Mountain Cabin under the pines. Close to town. Dogs ok.
Fridge, microwave, coffee/tea maker, toaster

Cabin in Rainbow

Tiny Cabin With Additional Open Air Sleeping Porch
10.0 out of 10, Exceptional, (21 reviews)
"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$1,259
HK$2,188 total
includes taxes & fees
16 Mar - 17 Mar
Tiny Cabin With Additional Open Air Sleeping Porch
Outdoor spa tub

Cabin in Idyllwild-Pine Cove

Idyllcottage: Located in Historic District with Spa, Fireplace, AC, Fenced-Patio, and Pet-Friendly!
10.0 out of 10, Exceptional, (49 reviews)
"As always, Kelly has the best cabins. From a cozy place to having everything well stocked, we always enjoy our time."
United States
Jorge L.
The price is HK$1,790
HK$3,346 total
includes taxes & fees
8 Mar - 9 Mar
Idyllcottage: Located in Historic District with Spa, Fireplace, AC, Fenced-Patio, and Pet-Friendly!
Exterior detail

Cottage in Valle De Los Caballos

Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
9.8 out of 10, Exceptional, (10 reviews)
"Surprised my wife with a trip to Temecula and found this lovely spot on a working farm. We both loved the atmosphere and the experience around the animals was incredible. The hosts were fantastic. Definitely recommend for an animal lover getaway or a cottage stay located close to every attraction/activity in the greater valley."
United States
Brice H.
The price is HK$2,151
HK$3,043 total
includes taxes & fees
9 Mar - 10 Mar
Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
Property grounds

Cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
8.8 out of 10, Excellent, (21 reviews)
"The place was great and so relaxing to stay in such a peaceful space."
United States
Rich C.
The price is HK$548
HK$1,291 total
includes taxes & fees
23 Mar - 24 Mar
Secluded mystical cabin in Idyllwild-Pine Cove
Property grounds

Cottage in Valley Center

Moonrise Cottage at Buena Terra Lavender Farm
10.0 out of 10, Exceptional, (7 reviews)
"The place was awesome super beautiful place and the hosts are very kind and welcoming!"
United States
Matthew S.
The price is HK$1,584
HK$2,528 total
includes taxes & fees
9 Mar - 10 Mar
Moonrise Cottage at Buena Terra Lavender Farm
Fridge, microwave, oven, stovetop

Holiday Home in Hemet

Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!
10.0 out of 10, Exceptional, (25 reviews)
"Nice place to stay, comfortable and clean. Really enjoyed the goats and other animals. "
United States
Kelsey N.
The price is HK$1,689
HK$3,229 total
includes taxes & fees
10 Mar - 11 Mar
Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!
Terrace/patio

Cabin in Idyllwild-Pine Cove

The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe
9.8 out of 10, Exceptional, (25 reviews)
"Had a great time! "
United States
Jimmy S
The price is HK$1,087
HK$2,538 total
includes taxes & fees
8 Mar - 9 Mar
The Nest: Serene Sanctuary w Hot Tub, Fireplace, Grill, Hammock, Outdoor Fire Fe
Interior

Cottage in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
The price is HK$813
HK$2,075 total
includes taxes & fees
16 Mar - 17 Mar
Hike, Sip & Explore: Couples Retreat in Fallbrook
Property grounds

Villa in Cross Creek

🦸🏻‍♂️The Iron Mansion 9 Acre Luxurious Private Resort 12000 ft Event Space!🏰
10.0 out of 10, Exceptional, (36 reviews)
"The place was amazing! "
United States
Kim R.
The price is HK$4,600
HK$11,036 total
includes taxes & fees
8 Mar - 9 Mar
🦸🏻‍♂️The Iron Mansion 9 Acre Luxurious Private Resort 12000 ft Event Space!🏰
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

Ayres Hotel & Spa Moreno Valley

Ayres Hotel & Spa Moreno Valley

10/10 Excellent
"Very nice hotel overall. Excellent free breakfast with omelette station and bar with taco during week. When I checked in at 6 pm hotel was full and the only room available had no working TV. I was offered a 50% discount for that night, negotiated that night to be free but folio only shows the 50% discount. Will follow up but maybe I will hear from Ayres to correct this in light of my positive review? Stay tuned. "
Cary 3-night trip
Posted 2 hours ago
Ayres Hotel & Spa Moreno Valley

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?

Idyllwild Realty Vacations: This holiday home rental outside of Winchester comes with free 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 5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views! and 1 Bed Room Casita-Suite with Private Entrance.

How many holiday rentals will I find in Winchester?

Choose from 33 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.