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Winchester Holiday Rentals

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Holiday Rentals in Winchester

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (36)
"Very friendly host. Very spacious, quiet place. Perfect for our family for my son's wedding in Fallbrook. "
Chateau Vino - French Style Chalet

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (38)
"This casita was the most perfect place for me to stay. The host, Elizabeth, sure packs a punch in the casita with everything you could possibly need. Relaxing, beautiful, quiet and safe. Elizabeth was very communicative before my arrival and during my stay. Very responsive. I would definitely stay here again, over and over. Thank you Elizabeth and VRBO for offering this casita. "
The price is AU$216
includes taxes & fees
12 Mar - 13 Mar
1/Bed Room Casita-Suite with Private Entrance

Wine Country Resort - Close to Wineries

Wine Country Resort - Close to Wineries

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (17)
"This was by far one of the best places I've stayed. Everything was exceptional! Little touches like water bottles, toothbrushes (in case you forgot yours) to cereal, coffee, real cream, wine and other goodies. The pool and hot tub were beautiful and easy to turn on. Fun games and plenty of room for the 6 of us on a girl's wine tasting birthday weekend. Highly, highly recommend. Beds were very comfortable (pillows were a little hard so if you want soft pillows you might want to bring your own)...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

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

2.0 star property
8.8 out of 10, Excellent, (3)
"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 AU$2,862
includes taxes & fees
12 Mar - 13 Mar
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

Sip and Swim Just Minutes From Temecula's Wine Country

10.0 out of 10, Exceptional, (18)
"Loved it. Very easy to communicate with the owner. The backyard looks like a tropical oasis. Very easy checking in & out process. clean & roomy. Several board games to choose from. "
Sip and Swim Just Minutes From Temecula's Wine Country

Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,

2.0 star property
10.0 out of 10, Exceptional, (5)
"Everything was perfect, we had an amazing experience, highly recommended "
The price is AU$731
includes taxes & fees
16 Mar - 17 Mar
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.4 out of 10, Exceptional, (52)
"Great safe clean place. No hallways, no rooms overhead or loud neighbors next door. A very nice Resort style RV park with basically Tiny Homes for rent. Plus so many fun things to do onsite as well as locations close to property. Lots of shopping and food nearby. My go-to place when coming to Hemet area "
The price is AU$283
includes taxes & fees
12 Mar - 13 Mar
The Cottages at Golden Village Palms RV Resort

Cozy Cottage, on the creek w/ hot tub!

8.8 out of 10, Excellent, (22)
"Awesome "
Cozy Cottage, on the creek w/ hot tub!

Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

2.0 star property
9.6 out of 10, Exceptional, (40)
"We had an amazing experience at this property. The space was enormous and regal, offering the perfect setting for our event. The view of the lake, especially during the sunrise, was breathless! The property manager, Daniel, was incredibly responsive and helpful, promptly answering our numerous questions. The highlight of the experience was Daniel's outstanding assistance when we accidentally left a bag behind—he went above and beyond to ensure we got it back. We had a fantastic time and highly...
Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

8.4 out of 10, Very good, (7)
"Overall, everything was good. The house is lacking a few essential items (like oven mits and cleaning spray to wipe down counters) but it worked great for our large group. Location was more remote than expected, but it was absolutely beautiful. Ran into a few minor issues during our stay but always received a timely response from the property manager in a professional manner."
20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

9.2 out of 10, Wonderful, (30)
"Needed to book a house for my friends wedding. House was perfect lots of room very clean. Beautiful views we all had a good timeWould book again "
The price is AU$984
includes taxes & fees
13 Mar - 14 Mar
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

Villa 5B/3B with pool/spa/mini golf putting

9.2 out of 10, Wonderful, (18)
"We were at group of about 11guests and the home felt spacious. Enjoyed the jacuzzi and the proximity to some of the best wineries! The management was prompt to reply to our messages. Wonderful stay… will definitely recommend to grit!"
The price is AU$1,789
includes taxes & fees
12 Mar - 13 Mar
Villa 5B/3B with pool/spa/mini golf putting

Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

9.8 out of 10, Exceptional, (101)
"This VRBO was truly amazing. We had a large group & Vlada’s place was perfect. No one felt crowded, plenty of amenities & the kitchen was perfect for preparing large meals. Vlada was very friendly & she made herself available with quick response to any questions or concerns. "
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views

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

3.0 star property
9.8 out of 10, Exceptional, (17)
"We thought this place looked fun and interesting and we were right! Every room was unique and the owner gave us a personal tour of his orchard. He even had props for us to use when taking our picture with his dinosaur statues!"
The price is AU$229
includes taxes & fees
12 Mar - 13 Mar
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center

3-Acre Estate with View, Gated Avenue, 3000 Sq Ft

The price is AU$742
includes taxes & fees
12 Mar - 13 Mar
3-Acre Estate with View, Gated Avenue, 3000 Sq Ft

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

The price is AU$84
includes taxes & fees
17 Mar - 18 Mar
Bring your peace or your party - more seclusion with less intrusion - adults 21+

Coral Tree House

3.0 star property
10.0 out of 10, Exceptional, (19)
"It was peaceful and beautiful! It’s a great place to just escape for a little while "
Coral Tree House

Fallbrook Tuscan villa oasis!

9.8 out of 10, Exceptional, (111)
"Great rental property with a very nice host. The home is well stocked, including toys for the kids to play with. The pool was clean and heated. A great place to spend a few days with family. "
Fallbrook Tuscan villa oasis!

The Little Cabin 🌲The coziest cabin on the Mountain.

10.0 out of 10, Exceptional, (73)
"My wife and I have gone up to stay in Idyllwild several times and we both agree this was our favorite cabin. It was so clean and tidy inside that I would have thought it was a new build. We also loved the massive yard with a gate so we could let our dog roam around and locate all the good sunny spots. The cabin is located smack dab in the middle of where I wanted to be. Less than 5 minute drive to Humber park with all the great trails and the same distance to town center. Communication with...
The Little Cabin 🌲The coziest cabin on the Mountain.
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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Other types of properties in Winchester you may be interested in

Pala Casino Spa And Resort

4.0 star property
8.8 out of 10, Excellent, (2976)
"Liked"
The price is AU$218
includes taxes & fees
12 Mar - 13 Mar
Pala Casino Spa And Resort

Hotel Xola

2.5 star property
7.8 out of 10, Good, (908)
"I liked this hotel for its comfort and because it was quiet. It did have some wear and tear that could be fixed. "
The price is AU$114
includes taxes & fees
30 Mar - 31 Mar
Hotel Xola

Pala Mesa Golf Resort

3.5 star property
9.0 out of 10, Wonderful, (428)
"I know it said no room services for food. But it did say can call to order for pick up. No menu was available in the room or online. And when I called to order the lady answered seemed not to be pleased that I was wanting to order from my room and just pick up. She was not helpful with the menu."
The price is AU$241
includes taxes & fees
16 Mar - 17 Mar
Pala Mesa Golf Resort
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.

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. Some other homes for rent in Winchester include Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball and Wine Country Resort - Close to Wineries.

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 Western Science Center, or get out into nature at a spot like Diamond Valley Lake Marina. Pechanga Resort & Casino and Mt. San Jacinto College 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.