Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

Outdoor pool

1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
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 ￥7,971
￥20,221 total
includes taxes & fees
Feb 24 - Feb 25
1 Bed Room Casita-Suite with Private Entrance
Property grounds

Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
Idyllwild-Pine Cove
9.0 out of 10, Wonderful, (19 reviews)
"Lots of wildlife, very rustic cabin experience "
United States
Robert H.
The price is ￥9,620
￥24,127 total
includes taxes & fees
Feb 16 - Feb 17
Secluded mystical cabin in Idyllwild-Pine Cove
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

3RV/ parking/Netflix/ private/excellent location

3RV/ parking/Netflix/ private/excellent location
Moreno Valley
8.6 out of 10, Excellent, (8 reviews)
"Communication with host was good , decently priced not a bad stay "
United States
Roger P.
The price is ￥7,482
￥25,806 total
includes taxes & fees
Feb 27 - Feb 28
3RV/ parking/Netflix/ private/excellent location
Terrace/patio

Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler

Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
Menifee
10.0 out of 10, Exceptional, (15 reviews)
"Great place!"
United States
JoePiccoloh
The price is ￥15,117
￥20,003 total
includes taxes & fees
Feb 16 - Feb 17
Casita Menifee Cozy and private 1 bedroom Casita, couple or solo traveler
Property grounds

Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo

Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (12 reviews)
"The Loft was adorable, just as pictured. Everything was neat, clean & air cooled for our comfort. Check in was simple, the WiFi worked great and the fire pit was fun to enjoy each night. We will definitely be back for a chill stay!"
United States
Mana N.
The price is ￥13,438
￥31,731 total
includes taxes & fees
Feb 25 - Feb 26
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
House (1 Bedroom) | Interior

Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is ￥15,881
￥40,519 total
includes taxes & fees
Feb 19 - Feb 20
Hike, Sip & Explore: Couples Retreat in Fallbrook
Smart TV

SALE! Peaceful, Clean, 4x Queen Bed, Spacious!

SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Hemet
9.0 out of 10, Wonderful, (2 reviews)
"Needed a safe place to stay in California for a month with 2 children. The cameras on the outside provided the security we were looking for."
United States
Shana W.
The price is ￥16,492
￥48,712 total
includes taxes & fees
Feb 15 - Feb 16
SALE! Peaceful, Clean, 4x Queen Bed, Spacious!
Outdoor dining

Beautifully remodeled mountain home with peaceful, private setting

Beautifully remodeled mountain home with peaceful, private setting
Fern Valley
8.8 out of 10, Excellent, (72 reviews)
"Very clean beaautifful,restful, enjoyed our stay "
United States
Valerie M.
The price is ￥13,590
￥41,565 total
includes taxes & fees
Feb 17 - Feb 18
Beautifully remodeled mountain home with peaceful, private setting
Outdoor spa tub

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

Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Idyllwild
8.4 out of 10, Very Good, (136 reviews)
"Was a cute quaint cabin, got the cabin details a head of time which was very reassuring. Has a wonderful decor."
United States
Michael
The price is ￥16,644
￥44,616 total
includes taxes & fees
Feb 23 - Feb 24
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Interior

La Petite - Heart of Town - Stunning Remodel

La Petite - Heart of Town - Stunning Remodel
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (16 reviews)
"The cabin was excellent it was very clean and had everything we needed for our stay. "
United States
michael
The price is ￥15,117
￥70,608 total
includes taxes & fees
Feb 28 - Mar 1
La Petite - Heart of Town - Stunning Remodel
Iron/ironing board, free WiFi

Idyllwild Realty Vacations

Idyllwild Realty Vacations
3.5 star property
Idyllwild
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 ￥18,429
￥20,272 total
includes taxes & fees
Feb 18 - Feb 19
Idyllwild Realty Vacations
Exterior detail

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town

Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
Idyllwild-Pine Cove
The price is ￥17,591
￥35,918 total
includes taxes & fees
Feb 23 - Feb 24
Cozy modern rustic 1-bedroom studio in Idyllwild. Perfect hideout close to town
Smart TV, video games, foosball, books

Endless Views & Spacious Home, Nature Games Weddings Wineries Hiking

Endless Views & Spacious Home, Nature Games Weddings Wineries Hiking
Fallbrook
10.0 out of 10, Exceptional, (18 reviews)
"Our hostess was awsome. Property very clean and plenty bathrooms"
United States
Terry H.
The price is ￥15,881
￥61,129 total
includes taxes & fees
Feb 23 - Feb 24
Endless Views & Spacious Home, Nature Games Weddings Wineries Hiking
Property grounds

Moonrise Cottage at Buena Terra Lavender Farm

Moonrise Cottage at Buena Terra Lavender Farm
Valley Center
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 ￥30,922
￥49,351 total
includes taxes & fees
Feb 16 - Feb 17
Moonrise Cottage at Buena Terra Lavender Farm
3 outdoor pools, pool umbrellas, sun 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, (83 reviews)
"Amazing stay, will visit again"
United States
Miguel
The price is ￥23,058
￥27,117 total
includes taxes & fees
Feb 16 - Feb 17
The Cottages at Golden Village Palms RV Resort
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, (6 reviews)
"It was the perfect escape from fireworks as my dog gets very anxious. It was very relaxing to be there."
United States
Brianna J.
Wildland Zen Den: Tiny House Retreat with Fireplace, Grill, AC, Hammock, Record
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, (1 review)
"Great stay, studio was very clean. Only thing was TV , was unable to program."
United States
Gloria P.
The price is ￥16,644
￥22,752 total
includes taxes & fees
Mar 1 - Mar 2
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Terrace/patio

Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK

Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (9 reviews)
"Great location, quiet and secluded. Loved the amenities, BBQ, HotTub, hammoc"
United States
Traian M.
The price is ￥16,797
￥47,184 total
includes taxes & fees
Feb 19 - Feb 20
Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK
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, (10 reviews)
"Host was great! Cabin was great! Couldn't recommend more!"
United States
Daniel L.
The price is ￥21,851
￥53,507 total
includes taxes & fees
Feb 17 - Feb 18
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
The Marylin Monroe: 1 Queen Bed, 1 Sofa Bed, Non-Smoking, CORP RATE | Individually decorated, individually furnished, desk, laptop workspace

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
Moreno Valley
9.8 out of 10, Exceptional, (23 reviews)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is ￥18,515
￥21,922 total
includes taxes & fees
Feb 15 - Feb 16
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
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
"All of it! Happy to be back again,my favorite place here!"
Susan 1-night trip
Posted 1 day 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 vacation rentals in Winchester?

Yes, you can find vacation rentals near well known sights in Winchester, or you can choose a secluded option if you're looking for relaxation. Winchester is known for its wineries and coffeehouses. Make sure you have time to check out the bars while you're in the area.

What's the top vacation rental in Winchester?

Idyllwild Realty Vacations: This vacation home near Winchester comes with free WiFi so you can feel at home during your trip. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Another good choice for your trip to Winchester is 1 Bed Room Casita-Suite with Private Entrance.

How many vacation rentals will I find in Winchester?

Choose from 32 Expedia vacation rentals in Winchester for a memorable vacation.

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 Lake Perris. K1 Circuit and Pechanga Resort & Casino are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private properties you can stay in for a short or long stay in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.