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Cottage holiday rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top Guest favourite
A bright living area features a yellow sofa adorned with colorful cushions. Natural light enters through multiple windows, illuminating the wooden floors and a cozy stone fireplace. A wooden coffee table is surrounded by art pieces, creating a welcoming space for relaxation.
Cottage in Temecula
4.99 out of 5 average rating, 385 reviews

Romantic, private and surrounded by best Wineries!

Isolate in your hot tub overlooking a private vineyard in the heart of Wine Country! Wine theme decor throughout this cottage. Bedroom simulates a barrel room, sleep on unique bed of wine boxes and barrels. Full kitchen plus BBQ grill to create your own fine gourmet meals or visit local fine dining. Enjoy gazing at the magical starry Temecula skies from the comfort of a private custom cedar hot tub. Bring your horse for $50/night. Safe Driver discounts for same day bookings as schedule permits.

Guest favourite
The studio features a bright sleeping area with a queen-sized bed adorned with decorative pillows. A cozy pullout sofa provides additional seating. Soft natural light enters through the sheer drapes, complemented by decorative wall accents and greenery, creating a peaceful ambiance.
Cottage in Riverside
4.86 out of 5 average rating, 166 reviews

Sweet Farmhouse - Kaiser - Parkview - CBU - UCR

DISCOUNT LONG TERM STAYS! This chic farmhouse style studio is fully renovated and professionally designed. Our home can comfortably fit up to 4 people. The home includes pull down blackout shades throughout, queen sized memory foam bed, A/C & heating unit, printer, fast Wi-Fi, Cable TV, 65 inch Smart TV, fully stocked kitchen with all cookware and basic spices, plush linens, shampoo/conditioner/body wash, spacious bathroom with large walk-in shower, and laundry basket with in-unit washer/dryer.

Superhost
A vibrant outdoor space is showcased, featuring a swimming pool surrounded by lush greenery. A Jacuzzi is positioned nearby, with a shaded seating area visible under a canopy. The inviting blue water reflects sunlight, creating a relaxing atmosphere perfect for gatherings.
Cottage in Nuevo
4.9 out of 5 average rating, 31 reviews

Ranch Style home near Temecula - Las Tres Marias

Charming Ranch-Style Cottage Near Temecula Wineries & Trails Pack your bags and escape to this beautiful ranch style cottage, nestled in a peaceful & scenic area perfect for a relaxing getaway with family & friends. Conveniently located just a short drive from Temecula's renowned wineries, Lake Perris, & surrounded by horse and hiking trails. Enjoy mornings with nature, spend the day wine tasting, or explore the local trails on foot or horseback. Bringing your horse? Stalls avaliable for a fee.

Superhost
Cottage in Fallbrook
4.96 out of 5 average rating, 269 reviews

Romantic Farm Stay with Hottub and View

Pet friendly, free parking, good wifi, private hottub, no shared spaces, smart lock easy self check ins. Tucked in the inland coastal hills of north San Diego, our organic subtropical farm is a great centrally located getaway destination. The beautiful 4-room space occupies the first floor of the original two-story, three-unit farmhouse on our family farm and has its own entrance with no shared spaces. Relax in the large, view, hot tub and enjoy the quiet! We have 5 other listings here as well.

Top Guest favourite
A pathway of cobblestones is visible, leading towards a rock formation and vibrant foliage. A statue of a figure with wings is positioned on a stone base, surrounded by autumn-colored trees, including red and yellow maples. The cozy cabin is seen in the background, framed by tall trees.
Cottage in Idyllwild-Pine Cove
4.99 out of 5 average rating, 158 reviews

Fern Creek Cottage

This cabin was built in 1922 and has been lovingly maintained & upgraded. We're walking distance to restaurants, shops & a local microbrewery. Our guest cottage features a private deck overlooking Strawberry Creek and a natural fern garden, providing the perfect retreat and ideal setting for your morning coffee or afternoon wine. The kitchen includes a vintage stove & refrigerator for light meal preparation & the bedroom comes with a SleepNumber bed for your personalized sleeping comfort.

Guest favourite
A cozy living area features a reclining loveseat adorned with a soft blanket. A dining table with black chairs is set near a small refrigerator. Artwork hangs on the walls, and natural light filters through the window with white blinds.
Cottage in Temecula
4.9 out of 5 average rating, 117 reviews

Rejuvenation Cottage -Wine Country Tranquility

Rejuvenate your spirit at this newly renovated cottage with privacy and tranquility on a large lot in the heart of the wine country, right behind Wilson Creek and Monte de Oro winery. Whether it's a spirit rejuvenation or a romantic getaway, this is the ideal place. Wake up and see the hot air balloons flow by, or enjoy the tranquility with a glass of wine on the front porch in the afternoon. With only one other house on this massive 4.6-acre lot, this is an experience unlike any other.

Superhost
An inviting cottage exterior is framed by natural stone and wooden accents, showcasing a white picket fence. A spacious deck features picnic tables and seating arrangements, surrounded by lush greenery and oak trees, creating a serene outdoor atmosphere.
Cottage in Temecula
4.86 out of 5 average rating, 576 reviews

Temecula Creek Cottages #6

One of 6 darling cottages renovated to new. Rent multiple cottages for you and your friends. Conveniently located near Temecula Wine Country, Old Town Temecula, and Pechanga, we are close to everything but still very secluded. Small dogs are allowed for a fee of $50 - passed on to our cleaning company for additional cleaning between guests. Unfortunately we do not allow cats due to allergy sensitivities. We also offer a Wedding and Event venue. Inquire about our special packages.

Top Guest favourite
A winding brick path leads toward a private deck nestled among lush greenery and vibrant plants.  A wooden railing borders the path, enhancing the natural setting and creating a welcoming approach to the cottage.
Cottage in Fallbrook
4.97 out of 5 average rating, 234 reviews

THE RAINBOW GUEST HOUSE

Perfect for a single couple, this private cottage is 800 sq ft. library/living room with a Samsung streaming TV and Wifi. Other features include a refrigerator, microwave, toasteroven, coffeemaker, barbecue, and multiple decks with views. Lots of books to read & and pool. Bedroom and large bath have all of the comforts of home, including heat/ac.This wonderful location (elevation 2,000) has ocean/mountain views. Please ask about pets. There is no food service but restaurant close

Top Guest favourite
A charming cottage is framed by tall trees, with an inviting entrance. The green exterior of the house blends harmoniously with the surroundings, and a stone pathway leads to the front door, inviting guests to explore the tranquil setting.
Cottage in Idyllwild-Pine Cove
4.97 out of 5 average rating, 158 reviews

Cozy cottage under the pines. With hot tub

Cozy and newly renovated, welcome to our getaway cottage in a cedar forest. Great outdoor space, jacuzzi tub and minimalist, mid-century furniture. Nestled among mature trees, the is a perfect getaway for a couple or solo traveler. Stretch out in a hammock or recline on a teak deck chair. Relax in the hot tub under the stars sipping your favorite drink. Cuddle up on the sofa with a fireside glow. Close to hiking trails, restaurants, unique shops, and art galleries. Cert 001856

Guest favourite
A spacious living area features a comfortable sectional sofa adorned with decorative cushions. Natural light filters through two large windows, dressed in soft, flowing curtains. The warm wood flooring complements the light-colored walls, creating an inviting space for relaxation.
Cottage in Lake Elsinore
4.89 out of 5 average rating, 102 reviews

Cozy Cottage / Less than 5 min walk to Lake!

Enjoy a nice and relaxing weekend getaway to Lake Elsinore! This cute cottage home is less than a 5 min walk to the lake and is just a half mile from Downtown Lake Elsinore where you can enjoy local eats on Main Street and Farmers Markets on Sundays! Our cottage is centrally located with many places to visit nearby: -Ortega Falls -Skydive Lake Elsinore - Glen Ivy Hot Springs -Temecula Wine Country- only a 20 min drive away!! -San Diego- only about an hour drive away!

Guest favourite
Cottage in Idyllwild-Pine Cove
4.94 out of 5 average rating, 113 reviews

Charming Fox Cottage w/ Wood Burning Fireplace

Take a deep breath of pine tree scented fresh air and come stay at our charming Fox Cottage! We encourage you to drop the weight of the world off at the front door and retreat into the beauty of the San Jacinto Mountains. With Humber Park nearby while also not too far from Idyllwild village. It's the perfect spot to recuperate after a long day of hiking or cuddle up next to the fire in the snowy mountains. We welcome you! Short term rental certificate #RVC-1785

Top Guest favourite
A covered outdoor area showcases a peaceful view of a sunlit landscape, featuring rolling hills and scattered trees. The gentle hues of dawn create a calming backdrop, emphasizing the spaciousness of the surrounding 5-acre property.
Cottage in Temecula
4.98 out of 5 average rating, 247 reviews

Horned Owl Cottage | 5 Acre Hill Top Views | Deck

Horned Owl Cottage, atop a 5-acre parcel, offers stunning sunrise views! ★ "Perfect getaway cottage! Close to all the wineries!" ☞ Top wineries with a 5 min drive ☞ Fully equipped + stocked kitchen ☞ 2nd level deck + porch w/ sunset views ☞ Onsite, secured parking for 1 vehicle ☞ Lemon trees on property ☞ Onsite washer + dryer ☞ Smart TV + 150 Mbps ☞ Keurig coffee maker 5 mins → DT Temecula (cafes, dining, shopping etc.) 15 mins → Old Town Temecula

Popular amenities for Winchester cottage rentals