
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.

Convenient King suite w/kitchenette + coffee bar
You won't find a more conveniently located place to stay! You will be close to all of the conveniences without all of the traffic and yet tucked away on a hilltop for peace and quite. You will be minutes from: restaurants, grocery stores, shopping, gas stations. You'll have easy access to the 215 freeway giving you close access to the wine country, casinos, malls and skydiving. You are only an hour from the beach, Big Bear mountain, Palm Springs/Coachella, Disneyland, SeaWorld, and LAX, etc.

Jet'd Spa-Outdoor Kitchen-Game Room-Massage Chair
Welcome to your own private oasis with stunning views in this spacious and tranquil retreat, enjoy the firepit & jetted hot tub, Massage chair & Game room ☞ 6-person hot tub ☞ Pool Table ☞ King Bed with ensuite ☞ Fenced yard ☞ Parking (onsite, 7 cars) ☞ Free 1Gbps Wi-Fi ✭Add my listing to your Wishlist by clicking ❤️the upper rt corner ☞ 5 Smart TVs (largest is 65 inches) ☞ Pet friendly ☞ Outdoor kitchen with gas BBQ ☞ Self check-in ☞ Onsite washer + dryer ☞ Fully equipped + stocked kitchen

Mountain Views Near Lake - Spacious Rural Retreat
15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our spacious property provides the atmosphere to unwind, rejuvenate and enjoy a peaceful stay in our rural setting. Our space features a classic and timeless aesthetic with elements such as a gambrel roof, extra-large picture windows, 180 degrees of clear mountain views & sunsets on the deck which overlooks the entirety of the property.

Soft Air...A Luxury suite with a view!
'Soft Air' is becoming a destination in itself. A getaway surrounded by nature, this Murrieta luxury suite in Temecula Valley overlooks an oak filled canyon... fresh ocean air! Close to wineries, your own private exterior entrance, king size bed, fireplace, large bathroom with soaking tub & shower...comfort & atmosphere. An exquisite experience! Enjoy the wonderful view from your own private spacious deck complete with a relaxing swing and outdoor kitchen. First morning breakfast included.

Charming One Bedroom Guest Suite Home
Charming Menifee Retreat: Fully Furnished One-Bedroom Home Discover a cozy home in the heart of Menifee, perfect for comfort and convenience. This fully furnished one-bedroom, one-bath residence offers a private entrance in a quiet neighborhood, less than two miles from the freeway. Centrally located between LA and San Diego, and minutes from Temecula wineries and Pechanga Casino. Amenities include a fully equipped kitchen, AC, electric fireplace, and safety essentials. NB: No Pets Allowed

Temecula - A Modern Cabin, BBQ, Fire pit, w/ VIEWS
This unique place has a style all its own. Handmade rustic ceilings being the highlight of this beautiful cabin. You'll be entering a one of a kind space with doors that open up to the back patio and view. Catch the sunrise and sunsets, and stargaze to the thousands of stars at night. Kick your feet up on the patio with a glass of wine, take a bath in our vintage tub, do some bbqing to the view, or relax with 2.5 acres of Mountain View’s. A peaceful stay that creates memories for a lifetime.

Private Cozy Casita with Kitchen/King bed
The Travelers Retreat Casita has all you’ll need to feel spoiled, including a Cal king bed with super soft bedding for the best nights sleep. Cook your own meals in our stocked kitchenette and full size refrigerator. The living room has a sofa that converts to a queen bed with a 3 inch latex topper. You must request for it and an extra guest fee applies. Also we have 2-TV’s with wifi and a washer dryer for your convenience. It’s all in the details and you will love all the amenities too.

Stunning Temecula Wine Country Oasis|Pool|Gameroom
Welcome to our exquisite Airbnb retreat in Temecula Wine Country. With a new pool, fully remodeled interior, all new mid-century modern furniture, including memory foam mattresses, exterior BBQ, pool table, and spa, Conveniently located minutes from wineries, Enjoy a glass of wine, or cook an exquisite meal in the backyard.Relax, unwind, and create unforgettable memories in your own slice of paradise. Book your stay with us today and embark on an extraordinary wine country adventure.

Beautiful RV on animal sanctuary in wine country
Our brand new RV is located in the heart of wine country. You can see the vineyards from the many panoramic windows throughout the trailer. You have your own private fenced in backyard and will be able to have our furry residents visit you throughout the day. Enjoy your morning coffee while seeing hot air balloons fly by or have a glass of wine by the gas fire pit while enjoying breathtaking sunsets. Our property is right next to the lake skinner as well as many wineries.

The Roadhouse Follow us at @roadhousewinecountry
The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!

Tuscan Retreat: Mountain Views & Sun-Drenched Yard
Welcome to The Cozy Charmer, your ultimate home-away-from-home! Spacious and Tastefully Decorated: Featuring 25-foot ceilings upon entry, this large 4-bedroom, 3-bathroom home is perfect for families, friends, or a work retreat. Stunning Outdoor Space: Enjoy sunsets and mountain views from the expansive backyard - perfect for a coffee or refreshing beverage. Book your stay today for an exceptional experience combining tranquility and adventure!

Ranch/Separate Private 2 Bdrm Suite w/Patio
Very private suite of 2 bedrooms that sleeps 5 people, your own private bath, a sitting area, and your own patio on a horse ranch with its own separate entry. Just 25 minutes drive from northern most end of the Temecula Wine Country. Guests enjoy use of an outdoor patio with mountain and ranch views, mini fridge, coffee maker and microwave. Suite is connected to our home but private. Families are especially welcome --
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester

Private Studio Oasis | Kitchenette | Washer/Dryer

Private King Suite + Amenities

Wineries, Views, Game Room & Spa - Hilltop Haven

SemperFi Casita:4 Beds/1 Bath/ Kitchen/Laundry/ADA

Country Hills Farm Stay

Peach Blossom Country House

Charming Casita By The Wineries - Cozy

Brand new home/close to wineries
Quick stats about vacation rentals in Winchester

Total vacation rentals
Explore 10 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at R498 ZAR per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Wi-Fi availability
10 of Winchester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
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