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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 €122
includes taxes & fees
27 Jul - 28 Jul
1 Bed Room Casita-Suite with Private Entrance

Wine Country Oasis Retreat - Close to wineries

10.0 out of 10, Exceptional, (52)
"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

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (45)
"Very friendly host. Very spacious, quiet place. Perfect for our family for my son's wedding in Fallbrook. "
Chateau Vino - French Style Chalet

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.4 out of 10, Exceptional, (67)
"The place was nice, great communication & very clean "
The price is €151
includes taxes & fees
23 Jul - 24 Jul
The Cottages at Golden Village Palms RV Resort

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

9.6 out of 10, Exceptional, (185)
"2nd time renting this property , perfect for any occasion "
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 €117
includes taxes & fees
1 Aug - 2 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

The price is €38
includes taxes & fees
11 Jul - 12 Jul
Adults 21+, Bring your peace or your party - more seclusion with less intrusion

Charming Fox Cottage w/ Wood Burning Fireplace

10.0 out of 10, Exceptional, (36)
"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

Hip, Secluded 2BR/2BA Cabin Unmatched Panoramic Views and Charm Among the Pines

10.0 out of 10, Exceptional, (106)
"We really enjoyed staying at this place. It has an amazing view to the mountains, it was very quiet so we were able to relaxed."
Hip, Secluded 2BR/2BA Cabin Unmatched Panoramic Views and Charm Among the Pines

House with pool/spa/minutes to wineries

8.8 out of 10, Excellent, (31)
"The host was vey attentive and helpful. A great place to stay. "
The price is €972
includes taxes & fees
13 Jul - 14 Jul
House with pool/spa/minutes to wineries

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

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

2.0 star property
9.6 out of 10, Exceptional, (41)
"Great space for large events, the new owners are amazing!"
Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

Best Choice for Party&Vacation Prestige Big House!

9.6 out of 10, Exceptional, (12)
"Perfect stay"
The price is €1,382
includes taxes & fees
15 Jul - 16 Jul
Best Choice for Party&Vacation Prestige Big House!

Luxury Gated Estate with Views of All of Wine Country!

9.6 out of 10, Exceptional, (179)
"Thanks for letting us stay the place was amazing as always!"
Luxury Gated Estate with Views of All of Wine Country!

Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

10.0 out of 10, Exceptional, (401)
"The house was beautiful and clean with a great location. Suzanne was friendly and great with communication. Check in was a breeze. Would definitely stay again"
Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

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!

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

2.0 star property
9.4 out of 10, Exceptional, (10)
"We came from nearby for a quick staycation, Meiko House fit our needs perfectly. Plenty of bedrooms with comfortable beds and bathroom space was plentiful. Yard and pool area well maintained. Recommend!"
The price is €300
includes taxes & fees
15 Jul - 16 Jul
Luxury 5-BR Villa w Pool, Hot Spa, Nature, 3000 sqft,

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

9.4 out of 10, Exceptional, (3)
"Had a great experience staying at this property. Huge land and space and very secluded from other neighbors. "
The price is €315
includes taxes & fees
16 Jul - 17 Jul
3-Acre Estate with View, Gated Avenue, 3000 Sq Ft

Resort Style Ranch/infinity pool for family

9.2 out of 10, Wonderful, (33)
"We loved the house, it was beautiful and even nicer in person. Loved the chefs kitchen and hot tub! Only wish the rooms had a few more curtains so it didn’t get as bright in the morning but we had a wonderful stay. We could stay again. Great house for groups or a big family vacation. "
The price is €1,060
includes taxes & fees
13 Jul - 14 Jul
Resort Style Ranch/infinity pool for family

Home on Organic Farm Near Wine Country and Casinos

9.4 out of 10, Exceptional, (39)
"Enjoyed our stay. A bit away from the beach scene, but nice and quiet."
Home on Organic Farm Near Wine Country and Casinos
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.