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Cottage vacation rentals in Winchester

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Top-rated cottage rentals in Winchester

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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, 381 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.

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 favorite

An outdoor seating area is nestled under a large tree, featuring comfortable wicker sofas with light cushions. A rectangular coffee table is surrounded by small, matching stools. Sunlight filters through the leaves, illuminating the space, and a wooden deck extends in the background.

Cottage in Pauma Valley

5 out of 5 average rating, 196 reviews

La Casita at Quixote Farm

You need a rest. See you soon™️ Since 2022, Quixote Farm has become a beloved getaway for countless guests who have returned time and again to enjoy the farms uniquely restorative effects. Modeled after a European farmstay, guests love walking in the orange groves, visiting with the rescue animals, shopping in the farmshop, enjoying a beautiful breakfast, or taking in our very popular sunset and charcuterie experience. Note:European Farmstays are exactly that: A family farm. Not a 5-star resort.

Top guest favorite

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, 155 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.

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, 116 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.

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, 573 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, 233 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 favorite

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, 155 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

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, 100 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 Idyllwild-Pine Cove

4.94 out of 5 average rating, 111 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

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, 242 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Winchester cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

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, 381 reviews

Romantic, private and surrounded by best Wineries!

Top guest favorite

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, 155 reviews

Cozy cottage under the pines. With hot tub

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

A serene outdoor area features two rustic seating options positioned on a concrete patio. In the background, a red barn stands in a well-maintained garden, surrounded by green bushes and a white picket fence. The space is shaded by nearby trees.

Cottage in Fallbrook

4.9 out of 5 average rating, 98 reviews

Farm Stay Bungalow And Hot Tub

Cottage in Fallbrook

4.96 out of 5 average rating, 269 reviews

Romantic Farm Stay with Hottub and View

The cottage is nestled among trees, showcasing a charming architectural style with a turret. A wooden deck extends from the side, providing a view of the surrounding greenery and hills. Native plants and landscaping adorn the foreground, enhancing the tranquil setting.

Cottage in Redlands

4.58 out of 5 average rating, 12 reviews

Cottage at the Historic Morey House

Pet-friendly cottage rentals

A charming cottage is set against a backdrop of lush greenery and large boulders. A wide staircase leads to a welcoming front porch, which is bordered by white railings and adorned with hanging plants. Tropical palm trees frame the scene, enhancing the tranquil setting.

Cottage in Temecula

4.85 out of 5 average rating, 586 reviews

Temecula Creek Cottages #1

A charming cottage is nestled among lush greenery and tiered granite hills. The exterior features a welcoming front porch with a wooden chair. Surrounding the cottage, a rustic stone wall adds character, while flowering plants create a vibrant touch against the natural backdrop.

Cottage in Temecula

4.85 out of 5 average rating, 583 reviews

Temecula Creek Cottages #2

The exterior of the cottage is surrounded by tall trees, with a spacious deck featuring a set of outdoor chairs. Large glass windows allow for natural light, and a wooden pathway leads to the entrance, framed by a stone border.

Cottage in Idyllwild-Pine Cove

4.9 out of 5 average rating, 20 reviews

Woodland View Cottage

A bright living area is showcased, featuring a light-colored sofa adorned with decorative pillows. A round mirror hangs on the peach-colored wall, reflecting natural light. A television is mounted above a wooden cabinet, and a small potted plant adds greenery to the space.

Cottage in Downtown Riverside

4.73 out of 5 average rating, 26 reviews

Downtown Riverside Boho Sanctuary

Top guest favorite

The cottage exterior showcases a welcoming yellow facade framed by lush greenery and vibrant flowers. Two wrought-iron chairs and a small table are positioned near large windows, inviting guests to enjoy the tranquil garden surroundings.

Cottage in Fallbrook

4.93 out of 5 average rating, 132 reviews

Country Cottage

Top guest favorite

A sunlit view of the exterior of Casita de la Maracuyá shows a welcoming yellow facade. A spacious patio is equipped with tables and chairs, surrounded by gravel and greenery. The nearby farm area is visible, completing the outdoor homestead setting.

Cottage in Fallbrook

5 out of 5 average rating, 15 reviews

Casita de la Maracuyá

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

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

4.71 out of 5 average rating, 136 reviews

Cozy cottage with a breathtaking view

Private cottage rentals

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

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

4.96 out of 5 average rating, 25 reviews

Cutest Cottage "The Sunflower House"

The bedroom features a modern queen bed with white bedding and decorative pillows. A geometric world map decorates the wall above, complemented by two framed prints on either side. Nightstands with metallic accents and a small plant add to the welcoming ambiance.

Cottage in Riverside

4.74 out of 5 average rating, 99 reviews

Midcentury Retreat - Kaiser - Parkview - CBU - UCR

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, 164 reviews

Sweet Farmhouse - Kaiser - Parkview - CBU - UCR

A charming cottage is surrounded by tall pines and cedars, featuring large glass windows that invite natural light. A spacious deck is equipped with a dining set, offering a peaceful outdoor space among the trees.

Cottage in Idyllwild-Pine Cove

4.91 out of 5 average rating, 46 reviews

Woodland Cottage- Mid Century Modern Beauty

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

4.68 out of 5 average rating, 19 reviews

Lovely Private Studio - UCR - LLU

A private porch is presented with two ornate wrought-iron chairs and a small table, overlooking expansive views of the surrounding hills and greenery. Bright blue skies create a serene backdrop, while natural light filters through the space.

Cottage in Temecula

4.95 out of 5 average rating, 251 reviews

Barn Owl Cottage ★Middle Of Wine Country★ Luxury

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