Winchester Vacation Rentals

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winchester vacation rentals

Outdoor dining
1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance

1 Bed Room Casita-Suite with Private Entrance
Winchester
9.8 out of 10, Exceptional, (62)
"Perfect little place to stay. very clean and cozy"
United States
Dillon P.
The price is ￥8,142
￥20,654 total
includes taxes & fees
Jan 11 - Jan 12, 2026
1 Bed Room Casita-Suite with Private Entrance
Outdoor pool
Coral Tree House

Coral Tree House

Coral Tree House
3.0 star property
Fallbrook
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 ￥25,111
￥37,258 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Coral Tree House
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

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)
"Our stay was pleasant, office manger kind and helpful with "
United States
CLAUDIA
The price is ￥18,004
￥21,316 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
Property grounds
Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove

Secluded mystical cabin in Idyllwild-Pine Cove
Idyllwild-Pine Cove
9.2 out of 10, Wonderful, (15)
"Nice rustic cabin close to town but secluded. "
United States
Jacob H.
The price is ￥10,918
￥25,735 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Secluded mystical cabin in Idyllwild-Pine Cove
Property grounds
Cactus Garden Cottage…Best Location!!

Cactus Garden Cottage…Best Location!!

Cactus Garden Cottage…Best Location!!
Fallbrook
10.0 out of 10, Exceptional, (54)
"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 ￥15,441
￥26,515 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Cactus Garden Cottage…Best Location!!
Interior
Off-grid A-Frame Cabin with expansive views

Off-grid A-Frame Cabin with expansive views

Off-grid A-Frame Cabin with expansive views
2.0 star property
Fallbrook
10.0 out of 10, Exceptional, (2)
"You can tell a lot of thought was put into this place. It is just the right balance of modern convenience and rustic adventure."
United States
Christine G.
The price is ￥19,839
￥26,078 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Off-grid A-Frame Cabin with expansive views
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

Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
2.0 star property
Idyllwild-Pine Cove
10.0 out of 10, Exceptional, (5)
"What a wonderful little home away from home! We chose this house for the completely fenced-in yard. We were so pleasantly surprised by the little unexpected amenities like gourmet loose-leaf tea, welcome champagne and a homemade candle to take home. There are beautiful hardwood floors in the living room, kitchen and bathroom; bedrooms both have comfortable carpeting. We stayed for 5 weeks... we have never stayed anywhere for that long and we would definitely stay here again. Margaret is an...
United States
Shanen A.
The price is ￥22,319
￥56,057 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
3 outdoor pools, pool umbrellas, sun loungers
The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.4 out of 10, Exceptional, (80)
"Amazing stay, will visit again"
United States
Miguel
The price is ￥23,551
￥27,697 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Cottages at Golden Village Palms RV Resort
Property grounds
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.

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
10.0 out of 10, Exceptional, (10)
"Very clean, I enjoyed the stay very quiet surroundings. "
United States
Sofia
The price is ￥16,096
￥38,372 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Exterior
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!

Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild-Pine Cove
9.6 out of 10, Exceptional, (28)
"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 ￥19,340
￥50,596 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
1 bedroom, iron/ironing board, WiFi, bed sheets
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property

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)
"Great stay, studio was very clean. Only thing was TV , was unable to program."
United States
Gloria P.
The price is ￥13,601
￥19,840 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Private Studio Oasis in Menifee - Kitchenette - Washer/Dryer - Gated Property
Fridge, microwave, oven, stovetop
Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!

Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!

Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!
Hemet
10.0 out of 10, Exceptional, (25)
"Nice place to stay, comfortable and clean. Really enjoyed the goats and other animals. "
United States
Kelsey N.
The price is ￥33,690
￥64,416 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace and Gaming Garage!
Fridge, microwave, oven, stovetop
Lakeside Escape, Cozy Getaway

Lakeside Escape, Cozy Getaway

Lakeside Escape, Cozy Getaway
2.0 star property
Lake Elsinore
The price is ￥16,704
￥25,438 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Lakeside Escape, Cozy Getaway
Outdoor spa tub
TheTiny Beach House at Coral Tree House

TheTiny Beach House at Coral Tree House

TheTiny Beach House at Coral Tree House
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 ￥25,111
￥44,433 total
includes taxes & fees
Jan 1 - Jan 2, 2026
TheTiny Beach House at Coral Tree House
Dining
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo

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)
"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 ￥13,725
￥32,254 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Outdoor spa tub
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

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, (7)
"We had a beautiful time at Clarity Cabin, made great use of the spa, it rained one day which was awesome, warm summer rains are so cozy. The upstairs bedroom is really cool, a great place to wake up…We lucked out as the other two cabins on the property were vacant at the time we were there so it was super private. We’d definitely stay there again when on the mountain. "
United States
Nathan P.
The price is ￥17,469
￥48,226 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Clarity Cabin: A-Frame Sanctuary w Hot Tub, Fireplace, Grill, AC, Hammock Chairs, Fire Pit, Pets OK
A heated pool
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub

3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub

3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
2.0 star property
Fallbrook
8.8 out of 10, Excellent, (13)
"Excellent house and location, great host communication."
United States
Jed H.
The price is ￥25,125
￥67,625 total
includes taxes & fees
Jan 5 - Jan 6, 2026
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub
Outdoor dining
Tiny Cabin With Additional Open Air Sleeping Porch

Tiny Cabin With Additional Open Air Sleeping Porch

Tiny Cabin With Additional Open Air Sleeping Porch
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 ￥25,111
￥44,900 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Tiny Cabin With Additional Open Air Sleeping Porch
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

Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Idyllwild
8.4 out of 10, Very Good, (135)
"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 ￥19,652
￥51,131 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Fridge, microwave, oven, stovetop
Peach Blossom Country House

Peach Blossom Country House

Peach Blossom Country House
Hemet
9.2 out of 10, Wonderful, (5)
"Communication with property host was very good. "
United States
Ken R.
The price is ￥28,854
￥56,305 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Peach Blossom Country House
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

MainStay Suites Moreno Valley Near March Air Reserve Base

MainStay Suites Moreno Valley Near March Air Reserve Base

10/10 Excellent
"Always a pressure to stay "
Keyandre 1-night trip
Posted 2 days ago
MainStay Suites Moreno Valley Near March Air Reserve Base

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?

1 Bed Room Casita-Suite with Private Entrance: This Winchester vacation home rental offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Make the most of the hot tub in this rental home to help you unwind. Our travelers also rate 5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views! as a favorite home for rent in Winchester.

How many vacation rentals will I find in Winchester?

Choose from 31 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.