Cottage vacation rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top guest favorite

A charming ranch cottage is visible, surrounded by carefully tended vineyards and a fenced area. Horses can be seen near the fence, complementing the tranquil rural setting. Lush trees rise in the background, highlighting the serene landscape of the Wine Country.

Cottage in Temecula

4.99 out of 5 average rating, 370 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 favorite

A gravel path winds through a green landscape, bordered by blooming trees, leading toward distant rolling hills. The mountains are visible in the background, framed by a clear blue sky with scattered clouds.

Cottage in Fallbrook

5 out of 5 average rating, 18 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

Top guest favorite

Cottage in Idyllwild-Pine Cove

4.99 out of 5 average rating, 140 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 favorite

Cottage in Fallbrook

4.95 out of 5 average rating, 261 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.

Top guest favorite

A wooden deck features two black seating chairs and a small round table. The surrounding landscape showcases rolling hills and mountain views under a clear blue sky, providing a serene outdoor space for relaxation.

Cottage in Pauma Valley

5 out of 5 average rating, 171 reviews

The Cottage at Quixote Avocado + Citrus 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. Whatever you decide to do, Quixote Farm will make you feel right at home.

Superhost

A serene outdoor space features a stone pathway leading to a wooden trellis framed by lush greenery and large rocks. Mature oak trees provide shade, while string lights hang softly overhead, enhancing the tranquil atmosphere of the garden.

Cottage in Temecula

4.85 out of 5 average rating, 568 reviews

Temecula Creek Cottages #2

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.

Guest favorite

A cozy library/living room is filled with shelves of books. Comfortable seating includes a leather sofa with red cushions and two chairs with matching decor. A lamp and a small table provide additional functionality, while a plush red area rug enhances the space's warmth.

Cottage in Fallbrook

4.97 out of 5 average rating, 215 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

The cottage is surrounded by mature trees, featuring a spacious deck with outdoor seating and string lights overhead. The entrance is visible, inviting guests into the cozy interior of the home. A hot tub can be seen in the background.

Cottage in Idyllwild-Pine Cove

4.97 out of 5 average rating, 136 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 favorite

A secluded studio cottage is nestled among tall trees, surrounded by natural woodland. A wooden fence encloses a small outdoor seating area composed of logs. The exterior showcases warm wooden tones and large windows, inviting light into the cozy space.

Cottage in Idyllwild-Pine Cove

4.96 out of 5 average rating, 155 reviews

Cozy mountain getaway, private cottage studio

This secluded studio is a perfect spot for a forest get-away. Tucked away from the street in a cedar grove on a nearly acre-sized property, this small cottage has cozy but modern vibes with forest-inspired touches. Use it as a crash pad as you experience all that Idyllwild has to offer (15 min walk to town), or stay in and relax with some records or video games. Drink your morning coffee among the trees. Perfect for a couples getaway. All-wheel drive recommended for winter stays

Guest favorite

A spacious outdoor area features a table with chairs beneath a large, shaded umbrella. Lush greenery and various potted plants surround the space, while citrus trees provide a natural backdrop. The patio area offers a comfortable setting for relaxation.

Cottage in Lake Elsinore

4.89 out of 5 average rating, 88 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!

Superhost

French doors open to a verdant outdoor area, revealing lush greenery and a sun lounge. Light filters in through the glass panes, enhancing the inviting atmosphere of the interior space.

Cottage in Bonsall

4.82 out of 5 average rating, 119 reviews

The Peppertree Cottage

Welcome to a very peaceful spot overlooking the beautiful Bonsall Valley in North San Diego. Located central to the beaches, wine country, and all the attractions San Diego has to offer. This is a house built for our friends to come stay on our 6 acre ranch. It’s very rare to have a country experience like this, so close to the ocean and the mountains! On a clear day, you can see both the coastline and some of the highest mountains in California.

Guest favorite

A stylish two-story home is showcased, featuring a combination of stucco and stone exterior elements. The driveway leads to a two-car garage, while lush green landscaping adds to the curb appeal. A welcoming front entrance is visible, enhanced by a decorative archway.

Cottage in Winchester

4.95 out of 5 average rating, 150 reviews

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.