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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
Cottage in Temecula
4.99 out of 5 average rating, 394 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.

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
4.91 out of 5 average rating, 34 reviews

Ranch Style home near Temecula - The Three Marys

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.

Guest favourite
Cottage in Fallbrook
4.96 out of 5 average rating, 275 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 charming cottage exterior is framed by natural landscaping. A covered porch with potted plants leads to the entrance, featuring a single door complemented by two windows. The surrounding area is dotted with trees offering shade and a serene atmosphere.
Cottage in Fallbrook
4.97 out of 5 average rating, 30 reviews

Cozy 1 BR Cottage at Welburn Gourd Farm

Our cozy 1 bedroom cottage, The Sunflower House is one of 3 cottages nestled within the embrace of our citrus and heritage oak trees on our historic 120-acre working gourd farm. This home has been meticulously updated and seamlessly blends quaint charm with modern luxury and comfort. Featuring 1 Bedroom + 1 Bath this cute cottage is set off in a private quiet tree canopied corner next to our sunflower field offering a private patio and pasture area. Amenities: fully equipped kitchen + free Wifi

A studio space features a spacious queen bed with a comfortable headboard and a cozy seating area, complemented by a dining table and chairs. Natural light filters through large windows, showcasing views of the outdoors. A stylish area rug covers the floor.
Cottage in Riverside
4.7 out of 5 average rating, 20 reviews

Lovely Private Studio - UCR - LLU

This lovely studio is a new construction which located in a very quiet cul de sac. It attached to the main house in one side and isn’t contiguous to any neighbor. Small but fully equipped, making it perfect for solo travelers or couples who work or take vacation in this area. The home includes a queen bed, A/C & heating unit, Wi-Fi, full kitchen with all cookware and brand new appliances, full bathroom, big closet with mirror door, plush linens, shampoo/conditioner/body wash, and keyless entry.

Superhost
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
4.87 out of 5 average rating, 130 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
4.85 out of 5 average rating, 590 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.

Cottage in Lake Elsinore
4.84 out of 5 average rating, 107 reviews

Mountain View Cottage on Private Farm

Visit our cozy cabin on a serene 10-acre farm in the Elsinore Mountains. Marvel at sweeping vistas of majestic rock formations and Oak woodlands from the Cleveland National Forest. Drift off to sleep to the tranquil sounds of seasonal creeks and chirping frogs. Wake up to a complimentary serenade from our resident roosters, goats, donkeys, and horses. Just a short drive from the beach yet secluded in the national forest, with miles of trails and cascading waterfalls awaiting exploration.

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, 111 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!

Cottage in Temecula
4.67 out of 5 average rating, 3 reviews

Starlit Suite for Two

Escape to the heart of Temecula Wine Country! Perfect for wine tastings, family getaways, group trips, or relaxing retreats. This listing is for a cozy barn apartment close enough to enjoy all that Temecula has to offer, quiet enough to unwind and enjoy the bright starry sky at night. Minutes to 40+ wineries, Old Town, Pechanga Casino, and Temecula Creek Golf. This home offers a quiet retreat for guests seeking the ultimate Temecula experience.

A spacious wooden deck extends outwards, offering unobstructed views of the surrounding hills. The area is adorned with several hummingbird feeders and a comfortable seating arrangement, complemented by potted plants, creating a serene environment for relaxation.
Cottage in Fallbrook
4.73 out of 5 average rating, 146 reviews

Cozy cottage with a breathtaking view

Nestled off the beaten path & a 10min drive to quaint downtown Fallbrook.Enjoy Nature in this 1.5 acres of pure tranquility & seclusion.Marvel the breathtaking sunsets &starlit skies. Help yourself to fruit trees that we have in the property. 5mins away from hiking & horse trails. 20mins away from Temecula. Fallbrook also have it’s variety of wineries & a treasure of it’s own. Definitely a place to stay to getaway from the busy life in the city.

Guest favourite
A cornhole board is positioned on a sandy surface, featuring the name 'Peppertree Ranch'. Colorful bean bags in purple and red are arranged for play. In the background, a farmhouse with a porch is visible, surrounded by trees and open space.
Cottage in Temecula
4.96 out of 5 average rating, 67 reviews

The Cottage at Peppertree Lane Ranch

Welcome to the Cottage at Peppertree Lane Ranch, your personal farmhouse-style getaway in the heart of Temecula Wine Country! We offer an upscale home on a seven-acre guest ranch surrounded by vineyards. The wineries of Palumbo and Lorenzi are our immediate neighbors, and with direct gated access to vineyard trails, a number of major wineries are a short walk away, including Bottaia, Wines, Ponte, South Coast, and Monte de Oro.

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