Winchester Vacation Rentals

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Dec 6 - Dec 7
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Dec 7 - Dec 8
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Winchester

Outdoor dining
1 Bed Room Casita-Suite with Private Entrance

Vacation Home in Winchester

9.8 out of 10, Exceptional, (59)
"Very nice property"
United States
Dillon T.
The price is ￥8,098
￥20,543 total
includes taxes & fees
Dec 10 - Dec 11
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 ￥19,790
￥31,470 total
includes taxes & fees
Dec 7 - Dec 8
Coral Tree House
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 ￥21,948
￥43,005 total
includes taxes & fees
Dec 16 - Dec 17
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
3 outdoor pools, pool umbrellas, sun 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 ￥23,425
￥27,547 total
includes taxes & fees
Dec 7 - Dec 8
The Cottages at Golden Village Palms RV Resort
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 ￥10,859
￥25,596 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Secluded mystical cabin in Idyllwild-Pine Cove
Property grounds
Twin Rock Tree House - Vintage Cabin

Cabin in Idyllwild-Pine Cove

9.8 out of 10, Exceptional, (29)
"We had a lovely stay, though it was short. We didn't really get to sit outside to enjoy the beauty or create a meal, but we were very much impressed!"
United States
Wendy W.
The price is ￥18,150
￥38,261 total
includes taxes & fees
Dec 8 - Dec 9
Twin Rock Tree House - Vintage Cabin
The Motorist Choice: Queen Bed and Hot Shower, Smoking & Non-smoking Room | 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 ￥17,907
￥21,202 total
includes taxes & fees
Dec 7 - Dec 8
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
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 ￥7,601
￥19,236 total
includes taxes & fees
Dec 14 - Dec 15
3RV/ parking/Netflix/ private/excellent location
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 ￥20,787
￥52,185 total
includes taxes & fees
Dec 11 - Dec 12
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
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 ￥15,358
￥26,217 total
includes taxes & fees
Dec 9 - Dec 10
Cactus Garden Cottage…Best Location!!
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 ￥16,009
￥37,854 total
includes taxes & fees
Dec 9 - Dec 10
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
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 ￥24,697
￥59,475 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
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 ￥20,038
￥44,875 total
includes taxes & fees
Dec 8 - Dec 9
Cozy cabin retreat nestled among forest trees
Suite | 2 bedrooms, Internet
Dog Friendly A-frame Hot Tub Nature Views

Apartment in Idyllwild

2.0 star property
The price is ￥22,401
￥50,443 total
includes taxes & fees
Dec 11 - Dec 12
Dog Friendly A-frame Hot Tub Nature Views
Outdoor spa tub
Dog-friendly mountain home with hot tub & amazing views - near town & hiking

Cabin in Idyllwild

8.4 out of 10, Very Good, (134)
"Enjoyed our stay "
United States
Cody
The price is ￥27,338
￥55,993 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Dining
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo

Apartment in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (12)
"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 ￥13,807
￥32,097 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Fridge, microwave, oven, stovetop
Lakeside Escape, Cozy Getaway

Vacation Home in Lake Elsinore

2.0 star property
The price is ￥13,527
￥22,059 total
includes taxes & fees
Dec 9 - Dec 10
Lakeside Escape, Cozy Getaway
Fridge, microwave, oven, stovetop
Peach Blossom Country House

Vacation Home in Hemet

9.2 out of 10, Wonderful, (5)
"Communication with property host was very good. "
United States
Ken R.
The price is ￥25,862
￥52,889 total
includes taxes & fees
Dec 10 - Dec 11
Peach Blossom Country House
Exterior
Hobbit House - Heart of Town - Stunning Remodel

Vacation Home in Idyllwild-Pine Cove

10.0 out of 10, Exceptional, (24)
"Clean, modern, well appointed and right in the heart of Idyllwild. The beds, pillows and linens were very comfortable and we all slept soundly."
United States
Jakk B.
The price is ￥24,045
￥84,623 total
includes taxes & fees
Dec 8 - Dec 9
Hobbit House - Heart of Town - Stunning Remodel
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 ￥17,219
￥47,795 total
includes taxes & fees
Dec 10 - Dec 11
Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK
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

Soboba Casino Resort

Soboba Casino Resort

10/10 Excellent
"Nice room, great staff, awesome golf course"
Fernando 2-night trip
Posted 2 days ago
Soboba Casino 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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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?

Exclusive Resort Style Estate in Temecula: This vacation home rental near Winchester is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Diamond Valley Lake Marina. 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.