Cottage vacation rentals in Winchester

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.

Value · Family · Long stay

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.

Value · Location · Kitchen

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.

Location · Family · View

Cozy Farm Cottage | Peaceful Nature Retreat

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 the historic 120-acre Welburn 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

Location · Family · Nearby

Temecula Wine Country Home

We are close to so much in the Temecula Valley, SUPERBOWL 2027 or OLYMPICS 2028 in LA, we are only 65 miles away. Galway Downs close by Welcome to our guesthouse situated in the middle of beautiful Temecula Wine Country where there is plenty of room for your family or friends to view the hot air balloons flying over the house in the early mornings. TV internet, FULL kitchen with granite. New bedroom and living room sets, clean linens and towels. Gazebo for your use. Walking distance to wineries.

Location · Family · Kitchen

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.

Value · Location · Getting around

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.

Location · Hospitality · Backyard

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.

Location · Family · Checkout

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.

Location · Family · Getting around

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!

Value · Location · Check-in

Farm Stay Bungalow And Hot Tub

Pet friendly, free parking, good wifi, full kitchen, very private, no shared spaces, smart lock easy self check ins. Tucked in the breezy inland coastal hills of north San Diego, our farm is a great centrally located getaway destination. The beautiful 2 bedroom guest house is private with its own private garden and outdoor picnic area tucked into the grove. Relax in the private hottub and enjoy the quiet! We have five other farmstay homes here if this one is booked.

Family · Location · Accuracy

Starlit Suite for Two

Escape to the heart of Temecula Wine Country! This cozy barn apartment on an equestrian estate is perfect for wine tasting weekends and romantic getaways. Minutes to 40+ wineries, Old Town, Pechanga Casino, and Temecula Creek Golf, yet quiet enough to unwind beneath starry skies. Countryside living means you may spot the occasional bug or critter, and the central heat and air can occasionally be finicky during a heavy rain — all part of the rustic charm!

Location · Value · Sleep quality