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Winchester Holiday Rentals

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Holiday Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (48)
"Perfect for a quick overnight stay. "
The price is AU$207
includes taxes & fees
18 Aug - 19 Aug
1 Bed Room Casita-Suite with Private Entrance

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (48)
"Really amazing stay! The hosts were so responsive and made sure that me and my friends were comfortable throughout our stay. The house was even better than the photos and it was so nice!! "
Chateau Vino - French Style Chalet

Wine Country Oasis Retreat - Close to wineries

10.0 out of 10, Exceptional, (57)
"The place was great. Very clean and with great amenities. Check in was smooth and the hosts were very responsive. "
Wine Country Oasis Retreat - Close to wineries

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

2.0 star property
9.0 out of 10, Wonderful, (6)
"A large group from our church stayed here for our church retreat. The property was very clean, was accurate to the listing, and communication with Sam was quick and efficient. There were many amenities and things to do in our free time! Sam did a great job ensuring that we would have a wonderful stay. We had such a great time and loved the property and would love to stay here again in the future!"
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.4 out of 10, Exceptional, (69)
"The place was nice, great communication & very clean "
The price is AU$273
includes taxes & fees
14 Sept - 15 Sept
The Cottages at Golden Village Palms RV Resort

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

9.6 out of 10, Exceptional, (187)
"Such a fun house to celebrate my wedding weekend in with family. Highly recommend."
Paradise Vacation Estate - Largest Luxury Private Vacation Resort

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

3.0 star property
9.8 out of 10, Exceptional, (21)
"Our stay was pleasant, office manger kind and helpful with "
The price is AU$210
includes taxes & fees
28 Aug - 29 Aug
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

Adults 21+, Bring your peace or your party - more seclusion with less intrusion

4.0 out of 10, (1)
"when we checked in, we had a few sites to choose from and but none of them seemed to fit our 10person tent, so we had "
The price is AU$65
includes taxes & fees
19 Aug - 20 Aug
Adults 21+, Bring your peace or your party - more seclusion with less intrusion

Luxury Gated Estate with Views of All of Wine Country!

9.8 out of 10, Exceptional, (181)
"Thanks for letting us stay the place was amazing as always!"
Luxury Gated Estate with Views of All of Wine Country!

Pet friendly cabin-Fully fenced yard! Pets stay free!

10.0 out of 10, Exceptional, (188)
"Cozy and comfortable. The best spot to bring the dogs. "
Pet friendly cabin-Fully fenced yard! Pets stay free!

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

2.0 star property
9.4 out of 10, Exceptional, (10)
"We had a great time at this vrbo! Close to restaurants, coffee shops and other shops.The pool and tub was amazing and there was plenty of space for our 12 person group.The only real downside was the coffee machine wasn't working when we were there and had issues using the outlets on that wall in the kitchen. "
The price is AU$502
includes taxes & fees
24 Aug - 25 Aug
3000 Sqft 5BR/4BTH Villa with Pool and Hot Tub

The Creek-Side Cabin: Spa, 5 Star, Upgraded, Big Deck, Quiet, Walk To Town

9.8 out of 10, Exceptional, (139)
"Comfortable and fun log cabin house:) we enjoyed our stay and look forward to returning in the future!"
The Creek-Side Cabin: Spa, 5 Star, Upgraded, Big Deck, Quiet, Walk To Town

Beautiful San Diego (Fallbrook) Retreat on 2+ Acres with Amazing Mountain View

9.8 out of 10, Exceptional, (89)
"house was very comfortable"
Beautiful San Diego (Fallbrook) Retreat on 2+ Acres with Amazing Mountain View

Coral Tree House

3.0 star property
10.0 out of 10, Exceptional, (19)
"Michelle and Greg were great host they very kind and generous. Very knowledgeable about the surrounding area. Absolutely lovely place to stay."
Coral Tree House

Cactus Garden Cottage…Best Location!!

10.0 out of 10, Exceptional, (46)
"Perfect little place and I was able to get Uber, so that was great!"
The price is AU$265
includes taxes & fees
29 Aug - 30 Aug
Cactus Garden Cottage…Best Location!!

The Most Popular Vacation Rental in Wine Country!

10.0 out of 10, Exceptional, (130)
"The location of this house was perfect being central to most wineries (also walking distance to a few). We loved the common spaces, especially the open kitchen / living space. Definitely recommend for a large group, as the # of bedrooms and bathrooms were perfect!"
The Most Popular Vacation Rental in Wine Country!

ROMANTIC LOG CABIN ~ Quiet, Clean, Cozy ~Walk to Trails, 3 Min to Town!

10.0 out of 10, Exceptional, (238)
"Had a wonderful time. The cabin was great, and the outside deck was beautiful. We enjoyed our time and wish we could have stayed longer. The nearby hiking was the best I’ve seen since North Carolina. Would love to come back again. "
ROMANTIC LOG CABIN ~ Quiet, Clean, Cozy ~Walk to Trails, 3 Min to Town!

5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

9.8 out of 10, Exceptional, (305)
"Our family loved the Strawberry Corner property for many reasons. The house gave each one of us the perfect place to relax and renew. We took turns in the hammock, swinging our worries away while gazing at the tall tree tops. The host's attention to details and decor made each room a delight. My daughter loved the Cowboy-themed bathroom with the big tub. My teenage son loved having his own "Cowboy Cabin", with TV and bathroom out by the game room. My mom and I loved working side by side in the...
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

Wine Country Cottage W/Amazing Pano-Great Reviews!

9.4 out of 10, Exceptional, (26)
"This listing is exactly as presented. Cute, comfortable and convenient for my needs! Just loved my time there! Be sure to watch for the hot air balloons that regularly float overhead - very cool!"
Wine Country Cottage W/Amazing Pano-Great Reviews!

Charming Fox Cottage w/ Wood Burning Fireplace

10.0 out of 10, Exceptional, (37)
"So cute and cozy- updated and andorable- easy check in - great appliances, kitchen necessities, bed, linens and bathroom. We already have recommended to friends!"
Charming Fox Cottage w/ Wood Burning Fireplace
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

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 31 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.