Holiday rentals in Winchester

Temecula Wine Country Home with Pool, Spa, & more!

Escape to our stunning and modern Temecula wine country home designed for comfort and relaxation! Located minutes from top wineries, this 3 BD/2.5 BA oasis offers a pool, spa, game room, and more! Perfect for wine tasting weekends, family reunions, or a relaxing getaway! The Highlights -Minutes from top Temecula wineries -Saltwater pool, hot tub, grill, fire pit -Open-concept layout with high-end furnishings, game room and fully-equipped kitchen -Comfortable bedrooms perfect for a restful stay

Brand new home/close to wineries

Single home with 3 BR, 2.5 BR with a 2-bay garage and one private open space. Open layout downstairs, great room, dining room and kitchen, walk-in pantry. Downstairs is a powder room. Upstairs, 2 secondary BR and a full BR along with the master suite. The secondary BR comes with dual sinks and tub/shower combo. The master suite features a bedroom and bathroom with dual sinks, vanity and shower, walk in closet. Laundry room upstairs along with a separate linen closet. Patio with BBQ grill.

Luxury Wine Country Retreatl Pool Spa & Game Room

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.

Tuscan Retreat: Private yard & Mountain views

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!

Vineyard Poolside Retreat

PLEASE NOTE THAT WHILE YOU'LL ENJOY THE PRIVACY OF YOUR OWN SPACE. THE HOUSE IS ATTACHED TO A SEPARATE GUEST APARTMENT WITH ITS OWN ENTRANCE, OTHER GUESTS MIGHT OR FAMILY MEMBERS MIGHT STAY THERE OCCASIONALLY , YOU'LL NOT SHARE THE FRONT STEPS AND DRIVEWAY, THE BACKYARD AND POOL ARE EXCLUSIVELY FOR YOUR USE. WE STRIVE TO MAINTAIN A QUIET ENVIRONMENT. FOR GUESTS WHO HAVE ONLY ONE OR NO REVIEWS WE REQUIRE A FULL REFUNDABLE SECURITY DEPOSIT OF $350.

20-Acre Retreat • Hot Tub + Panoramic Views

Welcome to Slice of Heaven by AvantStay, a 3BR/3BA Temecula retreat set on 20 peaceful acres above Lake Skinner with room for 11. Take in wide valley views, cook in the full kitchen, gather in the game room, or head outside for the hot tub, pickleball/basketball court, fire pit lounge, ping pong, scenic swing, view tower, and stargazing. 🌄 20 acres with Lake Skinner views ♨️ Hot tub, fire pit + scenic swing 🍷 15–22 min to Temecula wineries

The Wine Down Courtyard

Escape to Wine Down Court Yard in Winchester, just minutes from Temecula wineries! This ADU offers: Bedroom with Plush King bed Living Room with pull-out queen sofa Private Bathroom with essentials Kitchenette for light meals Close to wineries, shopping, dining, and Old Town Temecula. Enjoy free WiFi, smart TV, AC, and parking. Perfect for wine lovers, couples, or families. Relax, unwind, and “wine down” in this cozy retreat!

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 --

Carter's Wine Country Luxury Casita

This luxurious casita includes a queen bed and is the perfect retreat for the traveler wanting an opulent experience on an affordable budget. It has a private entrance with no common walls to the main home. There's a dedicated walk-in closet with washer and dryer. It also has a private bath and private courtyard entrance. This casita is located minutes from the Temecula wineries, and in a peace and quiet neighborhood.

Private Palm Tree Home with Huge Gated Yard!

🌿 Private rural home with a large gated yard and wide-open space. Located in a quiet country setting with easy access to the 215 freeway. The property offers plenty of parking for multiple vehicles, including RVs, boats, trailers, and work trucks. About 10 minutes from Menifee Town Center with shopping, dining, and essentials nearby. A simple, spacious stay with privacy, convenience, and room to park and relax.

6BR｜Pool&SPA｜Mini Golf｜Sauna｜10 Min to Winery

🌸 𝒫𝒾𝓃𝓀 𝒟𝓇𝑒𝒶𝓂 𝐸𝓈𝒸𝒶𝓅𝑒 – 𝐹𝓊𝓃, 𝒮𝓉𝓎𝓁𝒾𝓈𝒽, & 𝒰𝓃𝒻𝑜𝓇𝑔𝑒𝓉𝓉𝒶𝒷𝓁𝑒! 💖 Welcome to Winchester's most unique pink-themed retreat! This vibrant home is designed for fun, relaxation, and picture-perfect moments. 📍 Great location in Winchester—within a short 10-minute drive to shopping, dining, and Top winery！ 𝐵𝑜𝑜𝓀 𝓃𝑜𝓌 𝒶𝓃𝒹 𝑒𝓍𝓅𝑒𝓇𝒾𝑒𝓃𝒸𝑒 𝓅𝒾𝓃𝓀 𝓅𝒶𝓇𝒶𝒹𝒾𝓈𝑒!💕

Resort Pool & Spa. Temecula Wine Country Close.

Private resort living without leaving home. Swim under the sun, soak under the stars, and unwind in a spacious, design-forward home just 15 minutes from Temecula Wine Country. With a glowing pool, spa, firepit lounge, and multiple gathering spaces. This four-bedroom spa-inspired home is where you, your friends, and family can come to relax and enjoy a place away from it all.