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, 408 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 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, 163 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
Cottage in Temecula
5 out of 5 average rating, 42 reviews

Temecula Wine Country Home

WE'RE BACK!!!!!!!! IF you are going to the FIFA 2026, SUPERBOWL 2027 or OLYMPICS 2028 in LA, we are only 65 miles away. 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 counter tops. New bedroom and living room sets, clean linens and towels. Gazebo for your use. Walking distance to wineries.

Guest favorite
Cottage in Fallbrook
4.97 out of 5 average rating, 37 reviews

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

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
4.66 out of 5 average rating, 29 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.

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, 11 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 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, 598 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.

A charming cabin entrance features a white door framed by natural stone and surrounded by greenery. A pathway made of flat stones leads to the door, with oak trees and rocky hills visible in the background, creating a serene outdoor setting.
Cottage in Lake Elsinore
4.85 out of 5 average rating, 111 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 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, 131 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
Cottage in Fallbrook
4.9 out of 5 average rating, 105 reviews

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.

Superhost
Cottage in Temecula
4.54 out of 5 average rating, 13 reviews

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!

Top guest favorite
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
4.86 out of 5 average rating, 631 reviews

Temecula Creek Cottages #1

One of 6 darling cottages on a one and a half acre lot renovated to new. Rent multiple cottages for you and your friends. Conveniently located near Temecula Wine Country, Old Town Temecula, and Pechanga, but still very secluded. Small dogs are allowed for a fee of $50 - passed on to our cleaning service. Unfortunately we do not allow cats due to allergy sensitivities. We also offer a Wedding and Event venue. Inquire about our special packages.

Popular amenities for Winchester cottage rentals