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Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jul 11 - Jul 12
Tomorrow
Jul 12 - Jul 13
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Vacation Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance
Outdoor dining

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (46)
"Perfect for a quick overnight stay. "
The price is ￥8,481
￥20,296 total
includes taxes & fees
Aug 6 - Aug 7
1 Bed Room Casita-Suite with Private Entrance
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
Pool

Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

2.0 star property
9.0 out of 10, Wonderful, (6)
"8 cousins and our spouses (50-70 years old)were able to Spend 6 nights reminiscing our childhood memories and making more special memories. Our host, Sam was awesome and very personable to work with from the first day I booked! I recommend anywhere in the area to check it out!!"
The price is ￥143,292
￥268,741 total
includes taxes & fees
Jul 13 - Jul 14
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides
Outdoor pool

6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides

The price is ￥51,181
￥109,088 total
includes taxes & fees
Jul 24 - Jul 25
6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides
Beautifully remodeled mountain home with peaceful, private setting
Exterior

Beautifully remodeled mountain home with peaceful, private setting

8.8 out of 10, Excellent, (71)
"Very clean beaautifful,restful, enjoyed our stay "
The price is ￥14,331
￥47,525 total
includes taxes & fees
Jul 13 - Jul 14
Beautifully remodeled mountain home with peaceful, private setting
Classic Modern Walk Town Log Cabin
Interior

Classic Modern Walk Town Log Cabin

9.6 out of 10, Exceptional, (9)
"Everything was just right for a short weekend getaway ! Very nice, quiet, and conveniently located. Highly recommended!"
The price is ￥44,052
￥66,370 total
includes taxes & fees
Jul 18 - Jul 19
Classic Modern Walk Town Log Cabin
Beautiful lodge on creek, full bath, AC, WiFi, many amenities! Hot tub views!
Property grounds

Beautiful lodge on creek, full bath, AC, WiFi, many amenities! Hot tub views!

The price is ￥15,354
￥26,614 total
includes taxes & fees
Jul 21 - Jul 22
Beautiful lodge on creek, full bath, AC, WiFi, many amenities! Hot tub views!
La Petite - Heart of Town - Stunning Remodel
Exterior

La Petite - Heart of Town - Stunning Remodel

10.0 out of 10, Exceptional, (12)
"The place was so cute and it snowed when we visited which made it so magical! The host was also very communicative. "
The price is ￥18,279
￥67,924 total
includes taxes & fees
Jul 15 - Jul 16
La Petite - Heart of Town - Stunning Remodel
Hobbit House - Heart of Town - Stunning Remodel
Exterior

Hobbit House - Heart of Town - Stunning Remodel

9.8 out of 10, Exceptional, (17)
"Love this house. Cannot wait to stay again. "
The price is ￥22,666
￥77,648 total
includes taxes & fees
Jul 23 - Jul 24
Hobbit House - Heart of Town - Stunning Remodel
Best in town location•private•pro clean•dogs ok•kids play space•fire pit•loved!
Exterior detail

Best in town location•private•pro clean•dogs ok•kids play space•fire pit•loved!

10.0 out of 10, Exceptional, (146)
"Walk to bagels, upscale Italian, the movie theatre, ice cream, the gift shop. . Seriously awesome location. Will stay again. "
The price is ￥27,491
￥65,318 total
includes taxes & fees
Jul 28 - Jul 29
Best in town location•private•pro clean•dogs ok•kids play space•fire pit•loved!
Idy Hideaway: Picturesque Mountain Cabin in Perfect Location
Smart TV, fireplace, stereo, computer monitors

Idy Hideaway: Picturesque Mountain Cabin in Perfect Location

10.0 out of 10, Exceptional, (14)
"Perfect place to get together with family."
The price is ￥21,788
￥65,496 total
includes taxes & fees
Jul 24 - Jul 25
Idy Hideaway: Picturesque Mountain Cabin in Perfect Location
Creekside Yurt: EV Charger, New Heater/AC, Grill, Hammock, Pets OK
Exterior

Creekside Yurt: EV Charger, New Heater/AC, Grill, Hammock, Pets OK

10.0 out of 10, Exceptional, (1)
"This was fantastic. Very clean, very cool, it rained and we were very comfortable and warm while the sound of rain lasted all night.My wife was very happy with the experience. Ultra relaxing "
Creekside Yurt: EV Charger, New Heater/AC, Grill, Hammock, Pets OK
Spacious Sanctuary: Creek Access, Tesla Charger, Hammocks, Fire Pit, Pets OK
Exterior

Spacious Sanctuary: Creek Access, Tesla Charger, Hammocks, Fire Pit, Pets OK

10.0 out of 10, Exceptional, (6)
"It was the cutest place so clean and had everything we needed. Close enough to town and far enough to feel like your were in the woods. Loved it. Would definitely come back "
Spacious Sanctuary: Creek Access, Tesla Charger, Hammocks, Fire Pit, Pets OK
1/2 acre fenced•Dog&Kiddo Paradise•3rd Bdrm Option•Fire Pit•Sky Deck•Town Close
Outdoor dining

1/2 acre fenced•Dog&Kiddo Paradise•3rd Bdrm Option•Fire Pit•Sky Deck•Town Close

10.0 out of 10, Exceptional, (203)
"Especially enjoyed the fully fenced backyard with room for our dog to run around."
1/2 acre fenced•Dog&Kiddo Paradise•3rd Bdrm Option•Fire Pit•Sky Deck•Town Close
Peaceful A-Frame with Incredible Views
Interior

Peaceful A-Frame with Incredible Views

2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was great: clean, cozy, great location! I would stay there again."
The price is ￥27,053
￥49,476 total
includes taxes & fees
Jul 14 - Jul 15
Peaceful A-Frame with Incredible Views
"Rustic Elegance - A Woodland Escape"
Exterior

"Rustic Elegance - A Woodland Escape"

10.0 out of 10, Exceptional, (22)
"Mark’s place was absolutely perfect for our weekend in idyllwild. Easy checkin, close to town, quiet but cozy cabin, and lots of space. Would definitely book again when we come back!! "
"Rustic Elegance - A Woodland Escape"
Duplex House on the hill with a 3-bedroom in beautiful Banning with indoor pool.
Interior

Duplex House on the hill with a 3-bedroom in beautiful Banning with indoor pool.

The price is ￥73,115
￥88,140 total
includes taxes & fees
Jul 13 - Jul 14
Duplex House on the hill with a 3-bedroom in beautiful Banning with indoor pool.
Mountain View Oasis AC, Pool, Pet & Family Friendly
Pool

Mountain View Oasis AC, Pool, Pet & Family Friendly

10.0 out of 10, Exceptional, (1)
"We had a great time. Thank you for allowing us to experience your wonderful home. There are some features that I love. The space for parking is awesome and the pool was fantastic. Thank you again. "
The price is ￥42,114
￥94,061 total
includes taxes & fees
Jul 13 - Jul 14
Mountain View Oasis AC, Pool, Pet & Family Friendly
Spacious 3BR Home w/ Lake Access & Mountain Views
Fridge, microwave, oven, stovetop

Spacious 3BR Home w/ Lake Access & Mountain Views

8.8 out of 10, Excellent, (3)
"Comfortable and clean. Great Stay"
The price is ￥29,191
￥80,326 total
includes taxes & fees
Jul 18 - Jul 19
Spacious 3BR Home w/ Lake Access & Mountain Views
10min Soboba Casino Hemet Home with Hot tub+Lots of Parking grg/rv/boat/ATV's
Terrace/patio

10min Soboba Casino Hemet Home with Hot tub+Lots of Parking grg/rv/boat/ATV's

10.0 out of 10, Exceptional, (2)
"It was a nice place. I would recommend this rental.."
The price is ￥36,850
￥71,214 total
includes taxes & fees
Jul 22 - Jul 23
10min Soboba Casino Hemet Home with Hot tub+Lots of Parking grg/rv/boat/ATV's
Country Holiday House
Interior

Country Holiday House

9.6 out of 10, Exceptional, (4)
"My stay was very nice and quiet. Didn't have to worry about my safety and stores were very close to the property. The host was very accommodating and responsive. I would recommend staying at this property."
The price is ￥29,977
￥55,275 total
includes taxes & fees
Jul 14 - Jul 15
Country Holiday 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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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: Visitors give good reviews to this Winchester vacation home rental, which offers an outdoor pool, a pool table, 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.

How many vacation rentals will I find in Winchester?

Choose from 33 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. Pechanga Resort & Casino and Menifee Lakes Golf Course 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.