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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (46)
"Perfect for a quick overnight stay. "
The price is €121
includes taxes & fees
29 Jul - 30 Jul
1 Bed Room Casita-Suite with Private Entrance

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

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

The price is €556
includes taxes & fees
10 Aug - 11 Aug
6BR Pool Villa w/ BBQ - Near Wineries & Hot Air Balloon Rides

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 €286
includes taxes & fees
20 Jul - 21 Jul
Beautifully remodeled mountain home with peaceful, private setting

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!"
Classic Modern Walk Town Log Cabin

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

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

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 €411
includes taxes & fees
17 Jul - 18 Jul
La Petite - Heart of Town - Stunning Remodel

Hobbit House - Heart of Town - Stunning Remodel

9.8 out of 10, Exceptional, (17)
"Love this house. Cannot wait to stay again. "
Hobbit House - Heart of Town - Stunning Remodel

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 €388
includes taxes & fees
29 Jul - 30 Jul
Best in town location•private•pro clean•dogs ok•kids play space•fire pit•loved!

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 €394
includes taxes & fees
17 Jul - 18 Jul
Idy Hideaway: Picturesque Mountain Cabin in Perfect Location

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 "
The price is €223
includes taxes & fees
17 Jul - 18 Jul
Creekside Yurt: EV Charger, New Heater/AC, Grill, Hammock, Pets OK

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

10.0 out of 10, Exceptional, (204)
"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

2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was great: clean, cozy, great location! I would stay there again."
Peaceful A-Frame with Incredible Views

"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.

The price is €529
includes taxes & fees
20 Jul - 21 Jul
Duplex House on the hill with a 3-bedroom in beautiful Banning with indoor pool.

Mountain View Oasis AC, Pool, Pet & Family Friendly

10.0 out of 10, Exceptional, (2)
"This home is absolutely stunning! We celebrated my husbands birthday here just with family and it was perfect! Very quiet neighborhood and a beautiful view of the mountains. Very detailed as well with a mini bar, extra pool towels, games for a family game night and plenty of sitting area. Not to mention pretty stocked up kitchen with seasonings, coffee pods and different coffee syrup flavors. Plenty of dishes and kitchen needs. Pet friendly. They have an area to put your doggy outside to wonder...
The price is €568
includes taxes & fees
17 Jul - 18 Jul
Mountain View Oasis AC, Pool, Pet & Family Friendly

Spacious 3BR Home w/ Lake Access & Mountain Views

8.8 out of 10, Excellent, (3)
"Comfortable and clean. Great Stay"
Spacious 3BR Home w/ Lake Access & Mountain Views

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 €433
includes taxes & fees
29 Jul - 30 Jul
10min Soboba Casino Hemet Home with Hot tub+Lots of Parking grg/rv/boat/ATV's

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 €320
includes taxes & fees
29 Jul - 30 Jul
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 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?

1 Bed Room Casita-Suite with Private Entrance: This highly rated holiday home rental in Winchester offers an outdoor pool, a pool table and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. Make the most of Access to hot tub in this rental home to help you unwind.

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. Pechanga Resort & Casino and Menifee Lakes Golf Course 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.