Cottage vacation rentals in Winchester

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Winchester

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

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, 379 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.

A cozy sleeping area features a spacious bed adorned with soft white linens and vibrant yellow accent pillows. Floral wall art is displayed above, and a circular mirror reflects natural light. A decorative pillow with the phrase 'be our guest' adds a welcoming touch.

Cottage in Riverside

4.94 out of 5 average rating, 162 reviews

Riverside Studio - Kaiser - Parkview - CBU - UCR

DISCOUNT LONG TERM STAYS! This studio is fully renovated and professionally designed. Our cozy cottage is small, making it perfect for solo travelers or couples passing through the historic area of Riverside. The home includes a full sized memory foam bed, A/C & heating unit, printer/fast Wi-Fi, Cable TV, 55” Roku Smart TV, fully stocked kitchen with all cookware and basic spices, plush linens, shampoo/conditioner/body wash, laundry basket with onsite washer/dryer (in garage), and keyless entry.

Guest favorite

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

4.95 out of 5 average rating, 22 reviews

Cutest Cottage "The Sunflower House"

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

Guest favorite

A welcoming deck is equipped with several colorful outdoor chairs arranged around a central table. Lush greenery and rolling hills are visible in the background, creating a serene and natural setting.

Cottage in Fallbrook

4.96 out of 5 average rating, 268 reviews

Romantic Farm Stay with Hottub and View

Tucked in the hills of 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 five other farmstay homes here if this one is booked, or you'd like to reserve for a larger party. Romantic has a separate entrance with no shared spaces.

Guest favorite

A grand fountain features intricate sculptures and flowing water, set against a backdrop of classical architecture. The turquoise water glistens in the sunlight, inviting admiration from all who visit this historic site.

Cottage in Fallbrook

5 out of 5 average rating, 7 reviews

Lovely Roma Cottage in Fallbrook

Vacations are meant to be fun, relaxing, and adventurous. We add some special elements to the mix: enchanting, romantic, and magical! Come enjoy our unique picturesque Tuscan Villa and its gorgeous setting. Adventures await close by or check out the little village nearby for fun treasures. Step back in time with stunning antiques and old world charm in the villa or choose one of our whimsical cottages. In either case you will make great memories. Please read the rest of the description.

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

4.89 out of 5 average rating, 109 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, 567 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 favorite

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, 229 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

Guest favorite

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, 96 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 favorite

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

4.97 out of 5 average rating, 234 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

Superhost

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

4.74 out of 5 average rating, 133 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 favorite

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

4.95 out of 5 average rating, 64 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.