Winchester Vacation Rentals from ￥2,647: Search Short-Term Rentals

Q: 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.

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Vacation Rentals in Winchester

Situated in a residential neighborhood, this single-story home features a stucco exterior and a flat roof, with a front door and adjacent outdoor seating area.

"Perfect for a quick overnight stay. "

￥19,475 total

includes taxes & fees

Aug 6 - Aug 7

Stately two-story home with a central entrance, tall windows, and a gabled roof.

"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!! "

Relax on the patio with a sofa, coffee table, and fire feature, surrounded by a pergola and a view of the swimming pool.

"The place was great. Very clean and with great amenities. Check in was smooth and the hosts were very responsive. "

Relax by the pool surrounded by a brick border, with a staircase leading to a welcoming entrance.

"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!!"

￥302,270 total

includes taxes & fees

Jul 27 - Jul 28

Relax by the resort's multiple pools surrounded by palm trees and sun loungers.

"The place was nice, great communication & very clean "

￥26,116 total

includes taxes & fees

Jul 27 - Jul 28

Sit and enjoy the serene surroundings from this charming outdoor space with a bench and table.

￥5,880 total

includes taxes & fees

Jul 27 - Jul 28

Surrounded by lush gardens and a waterfall, this resort offers a serene escape with a large swimming pool and a warm, inviting atmosphere.

"Such a fun house to celebrate my wedding weekend in with family. Highly recommend."

Compact kitchen with gas stove, oven, microwave, and ample storage.

"Our stay was pleasant, office manger kind and helpful with "

￥20,100 total

includes taxes & fees

Aug 1 - Aug 2

￥78,167 total

includes taxes & fees

Aug 5 - Aug 6

Escape to a serene cabin surrounded by a lush forest and a beautifully maintained garden.

"So cute and cozy- updated and andorable- easy check in - great appliances, kitchen necessities, bed, linens and bathroom. We already have recommended to friends!"

Relax in the serene outdoor patio surrounded by lush greenery and a distant forest view.

"We loved this sweet little cabin for a girls weekend. Perfectly appointed, unreal views and great prep by the host. Thanks!"

Relax by the pool surrounded by lush vegetation and enjoy the peaceful atmosphere.

"Michelle and Greg were great host they very kind and generous. Very knowledgeable about the surrounding area. Absolutely lovely place to stay."

Stunning property with a symmetrical roofline, surrounded by lush vegetation and a well-manicured landscape.

"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. "

Relax by the serene pool surrounded by lush greenery and a hilly backdrop.

"We really enjoyed our weekend in Temecula - the space was lovely and accommodated our large group well. The pool is a bit small but many of us enjoyed sunbathing and sitting in the shallow area after wine tasting nearby. The landscape around the home was beautiful. Overall the space had everything we needed and the management was very responsive and helpful."

￥177,195 total

includes taxes & fees

Jul 27 - Jul 28

Relax by the serene pool surrounded by lush greenery and lounge chairs.

"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!"

￥51,004 total

includes taxes & fees

Aug 18 - Aug 19

Enjoy cooking in this well-equipped kitchen with a large island and modern appliances.

"Enjoyed the spaciousness of the property for our slumber party and Old Town weekend! Perfect for large family/friends to sit together at the table."

￥175,255 total

includes taxes & fees

Jul 27 - Jul 28

Enjoy a panoramic view of the surrounding landscape from this room's large window, overlooking a swimming pool and rolling hills.

"Thanks for letting us stay the place was amazing as always!"

Enjoy a refreshing swim in our pool surrounded by a beautifully manicured lawn.

"Perfect stay"

￥232,364 total

includes taxes & fees

Jul 28 - Jul 29

Enjoy a serene beach setting with a volleyball net and access to the calm waters via a concrete walkway.

"Great space for large events, the new owners are amazing!"

Enjoy a relaxing stay in this charming home with a spacious porch, outdoor seating area, and pool.

"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!"

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Top Winchester Hotel Reviews

Hilton Garden Inn Temecula, CA

10/10 Excellent

"Stay was excellent close by to restaurants "

Staybridge Suites Temecula Wine Country by IHG

10/10 Excellent

"Everything was great except until the last day not all the washers and dryers were working. Also the one elevator had a mind of its own. Other than that I love staying at this hotel. Will 100% recommend and most definitely will be staying here again. "

Motel 6 Temecula, CA - Historic Old Town

10/10 Excellent

"Of course it’s expected the weather brings in bugs nothing crazy rooms are small but they’re perfect to rest your head after a busy day exploring and going to parks could be cleaner was scared due to seeing a Review after checked in about bed bugs but we checked everything and they where clear "

Find out more about Winchester

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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.

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Winchester Vacation Rentals

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Vacation Rentals in Winchester

1 Bed Room Casita-Suite with Private Entrance

Chateau Vino - French Style Chalet

Wine Country Oasis Retreat - Close to wineries

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

The Cottages at Golden Village Palms RV Resort

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

Paradise Vacation Estate - Largest Luxury Private Vacation Resort

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

Fallbrook mediterranean house + ADU

Charming Fox Cottage w/ Wood Burning Fireplace

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

Coral Tree House

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

House with pool/spa/minutes to wineries

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

Villa with indoor pool in Temecula wine country-VRBO

Luxury Gated Estate with Views of All of Wine Country!

Best Choice for Party&Vacation Prestige Big House!

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

The Most Popular Vacation Rental in Wine Country!

Top Winchester Hotel Reviews

Hilton Garden Inn Temecula, CA

Staybridge Suites Temecula Wine Country by IHG

Pala Casino Spa And Resort

Ayres Hotel & Spa Moreno Valley

South Coast Winery Resort and Spa

Motel 6 Temecula, CA - Historic Old Town

Pala Mesa Golf Resort

Tahquitz Pines Retreat

MainStay Suites Moreno Valley Near March Air Reserve Base

Find out more about Winchester

Frequently asked questions