Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

The bathroom features a contemporary design with dark green walls and a stylish patterned floor. A freestanding sink with a gold frame is positioned against one wall, next to a glass shower enclosure showcasing shimmering green tiles. A mirror with an arched top reflects the modern aesthetic.

Home in Nuevo

4.89 out of 5 average rating, 63 reviews

Peaceful & Private w Stunning Mountain View’s

Our private, separate and detached guesthouse is located in a rural country setting with mountain views all around for those seeking a relaxing and peaceful atmosphere to unwind, relax, rest and rejuvenate, 15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our space features a modern contemporary aesthetic inside w stunning mountain views & sunsets on the deck to stargaze and unwind.

Guest favorite

A winding trail meanders through grassy hills adorned with patches of vibrant yellow wildflowers. The surrounding landscape consists of rolling hills under a clear blue sky, punctuated by scattered clouds, creating a serene outdoor environment.

Guest suite in Menifee

4.93 out of 5 average rating, 118 reviews

Convenient King suite w/kitchenette + coffee bar

You won't find a more conveniently located place to stay! You will be close to all of the conveniences without all of the traffic and yet tucked away on a hilltop for peace and quite. You will be minutes from: restaurants, grocery stores, shopping, gas stations. You'll have easy access to the 215 freeway giving you close access to the wine country, casinos, malls and skydiving. You are only an hour from the beach, Big Bear mountain, Palm Springs/Coachella, Disneyland, SeaWorld, and LAX, etc.

Superhost

The exterior view of the two-story house is captured at dusk, showcasing a well-lit facade. The backyard features a pool and a jacuzzi. Seating areas are arranged under a covered porch, providing options for relaxation amidst the surrounding lawn.

Home in Winchester

4.79 out of 5 average rating, 29 reviews

Vineyard Poolside Retreat

DEAR GUEST, PLEASE NOTE THAT WHLE YOU'LL ENJOY THE PRIVACY OF YOUR OWN SPACE. THE HOUSE IS ATTACHED TO A SEPARATE APARTMENT WITH ITS OWN RESIDENTS. YOU'LL SHARE THE FRONT STEPS AND DRIVEWAY BUT THE BACKYARD IS EXCLUSIVELY FOR YOUR USE. THE RESIDENTS MAY OCCASIONALLY ACCESS THE GARAGE TO CHARGE THEIR ELECTRIC VEHICLE BUT THEY DO NOT HAVE ACCESS TO YOUR AIRBNB SPACE. WE STRIVE TO MAINTAIN A QUIET ENVIRONMENT AND HOPE THIS SETUP ADDS TO YOUR COMFORT. FEEL FREE TO REACH OUT IF YOU HAVE ANY QUESTI

Top guest favorite

A welcoming living area is presented with two light-colored sofas positioned around a wooden coffee table. Natural light enters through windows adorned with sheer curtains. A mirror hangs on the wall, reflecting the cozy space, which features warm wood flooring and light-colored walls.

Home in Hemet

4.95 out of 5 average rating, 192 reviews

Colonial Cottage Get-A-Way

650 square feet of completely remodeled mobile home in quiet neighborhood. Ideal as a cozy retreat for a couple or single traveler. Large kitchen with all new appliances and plenty of utensils for those who like to cook. Formal dining area for guests you would like to entertain. Comfortable sitting area in living room. Cot available for a 3rd person . Private parking in a long driveway - so bring your SUV! Very close to all shopping. Plenty of free bottled water. You will love this place!

Superhost

A serene outdoor space is highlighted by a sparkling pool with a waterfall feature. Sun loungers are positioned nearby, and a shaded cabana provides a relaxing retreat. Lush greenery surrounds the area, creating a tranquil atmosphere for guests to enjoy.

Guest suite in Winchester

4.87 out of 5 average rating, 83 reviews

Wine Country Studio with Pool/Spa

This private studio has a style all its own, perfect for a romantic getaway, or fun trip with a friend. Elegantly decorated, located in a quiet neighborhood only 4 minutes to the closest winery, and near Old Town Temecula, it’s the perfect spot for a short stay. Amenities include a resort style pool and spa, complete with outdoor fireplace, fire bowls, waterfall, and s’mores fire table. Wake up to a view of the floating wine country balloons in the distance, often visible each morning.

Top guest favorite

Two goats are seen standing on a wooden picnic table. The goat on the left has a predominantly black coat with white markings on its legs, while the smaller goat on the right displays a light gray and brown coat. A sunny blue sky is visible in the background.

Camper/RV in Winchester

4.99 out of 5 average rating, 85 reviews

Beautiful RV on animal sanctuary in wine country

Our brand new RV is located in the heart of wine country. You can see the vineyards from the many panoramic windows throughout the trailer. You have your own private fenced in backyard and will be able to have our furry residents visit you throughout the day. Enjoy your morning coffee while seeing hot air balloons fly by or have a glass of wine by the gas fire pit while enjoying breathtaking sunsets. Our property is right next to the lake skinner as well as many wineries.

Top guest favorite

An open kitchen features rich wood cabinetry and stainless steel appliances. A round dining table with four chairs is positioned to the side, complemented by a vibrant vase of flowers. Natural light streams through sliding glass doors leading to the patio.

Home in Winchester

4.97 out of 5 average rating, 30 reviews

Temecula Valley Retreat

Just 10 minutes on back roads to Temecula's Wine Country & close to golf, shopping, Lake Skinner, motorcycle tracks & Pechanga Casino. The home is nicely decorated and well stocked with everything you need WITH LEVEL 2 EV CHARGING UPON REQUEST. Located in a quiet neighborhood with over 2600 sq feet of living space. Perfect for wine tasting adventures, bridal parties, or whatever it is that brings you and your family into town. Enjoy your stay.

Guest favorite

A cozy outdoor seating area is displayed, featuring a sectional sofa with plush gray cushions. A wooden coffee table sits at the center, accompanied by a decorative plant. Nearby, a modern fireplace adds a touch of warmth to the inviting courtyard setting.

Cottage in Winchester

4.95 out of 5 average rating, 153 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.

Top guest favorite

Farm stay in Menifee

5 out of 5 average rating, 124 reviews

Buckley Farm's Casita

The Casita is a newly remodeled little farm house. It’s located between 15 and 215 freeways on Bundy Canyon making it very accessible. It has a gated entrance, a relaxing feel with a full bath, kitchen and laundry. If your looking for a peaceful get away while still being close to all the amenities, this is it!! We are a small family farm with chickens, free ranging turkeys, peacocks, pigs dairy cows and more.

Top guest favorite

The exterior of a guesthouse is illuminated at night, showcasing landscaped greenery, including palm trees and decorative lighting. A winding path leads through the garden, and a driveway with a parked vehicle is visible. The inviting architecture features substantial windows and a charming entrance.

Guesthouse in Sun City

4.95 out of 5 average rating, 375 reviews

Private cozy Studio guesthouse

Cozy studio guesthouse is separate from our house, no connecting walls and in front of our house so we're available if you need anything. New queen-size cool-gel / memory foam mattress. Small area with refrigerator, Kherug coffee and microwave. Guests check in with smart code door lock. Close to wineries in Temecula and skydiving. 1-1.5 hours to beach, Disneyland and many amusement and water parks.

Guest favorite

A community pool area is depicted under a colorful sky filled with clouds at sunset. Several poolside lounge chairs are arranged around the water. Children splash and swim while adults relax nearby, creating a lively yet relaxed atmosphere.

Guest suite in Murrieta

4.93 out of 5 average rating, 180 reviews

Welcome to the Private Suite in French Valley!

The quiet and stylish private suite located in the countryside-style boomtown of French Valley, within 30-min driving distance from Temecula vineyard and downtown or hours distance from Palm Spring, San Diego, or Los Angeles. The hostess used to host people from all over of the worlds, and will do the best to make the guest’s comfortable stay regardless for leisure or business.

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 354 reviews

Cooper's Casita in Wine Country

This charming detached Casita in a quiet cul-de-sac is located near Temecula Wine Country and is just a short drive to local attractions. The kitchenette is equipped with a mini fridge, microwave, toaster oven and kitchen essentials. Queen bed with a full bathroom, walk-in closet, and tv w/ cable **Current Riverside County STR Certificate #002552**

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winchester

Guest favorite

The entrance features a well-maintained pathway leading to a covered porch. Lush greenery surrounds the area, with a palm and manicured grass enhancing the welcoming appearance. A white picket fence partially encloses the front yard, creating a charming entrance to the home.

Private room in Menifee

4.9 out of 5 average rating, 104 reviews

Peaceful and relaxing stay

Shannon NicoleRating, 5 stars1 month ago

Had a lovely time at Hector’s place. Extra comfy bed, affordable, spacious and peaceful. I would definitely recommend it to anyone.

Top guest favorite

An inviting outdoor space features a seating area with plush cushions beneath a large umbrella, illuminated by string lights. A built-in fireplace adds ambiance, while a putting green is present on the patio, creating an area suitable for relaxation and entertainment.

Private room in Lake Elsinore

4.96 out of 5 average rating, 296 reviews

Little piece of heaven.

FernandoRating, 5 stars1 week ago

George is a great host, his place is very comfortable and peaceful. Looking to stay again in the future.

Guest favorite

A well-lit hallway is flanked by two doors, leading to a bedroom and a bathroom. Soft carpeting covers the floor, while a black rug lays in front of the bathroom vanity. A window with dark curtains is visible in the bedroom, enhancing the inviting space.

Private room in Winchester

4.82 out of 5 average rating, 11 reviews

Private Bedroom/Shared Bathroom.

PhillipRating, 5 stars1 month ago

It was a good place for the price. I would probably continue booking this place if I wanted to come to Temecula again. Thank you for the flexible check in time!

Guest favorite

A kitchen space is shown with a light granite countertop. A decorative bowl containing corks is placed next to a power outlet, equipped with additional charging ports, for convenience. In the background, kitchen items such as paper towels and a coffee maker are visible.

Private room in Winchester

4.96 out of 5 average rating, 24 reviews

Private room/shared bath

AaronRating, 5 stars2 weeks ago

Cristina was a great host and bed and pillows were comfortable

Top guest favorite

Private room in Menifee

5 out of 5 average rating, 33 reviews

Stylish Room w/ full bath in Menifee

SrirajRating, 5 stars4 weeks ago

Quiet room and a clean bathroom available on the upper floor. Convenient location with easy access to restaurants, shops and other amenities. About 20min drive to Perris airport and other recreational facilities. Great value!

Top guest favorite

A well-lit bathroom features a double sink vanity with dark wood cabinetry. Two mirrors reflect the space, enhancing the openness. Navy blue towels are neatly hung on a rack, while decorative items are arranged on the countertop. A door leads to another area.

Private room in Murrieta

5 out of 5 average rating, 34 reviews

Lucky's In

JuliannaRating, 5 stars1 week ago

super nice family, very responsive host and so accommodating of my last minute booking :) also - cute cats and comfy bed!

Top guest favorite

An outdoor seating area features a glass-top table with a stacked Jenga game in front of a cozy couch. A decorative cushion on the couch displays the phrase 'MY HAPPY PLACE.' A potted plant adds greenery, enhancing the inviting space.

Private room in Murrieta

4.97 out of 5 average rating, 60 reviews

Peony Mini Suite: Wine Country Escape

CarolRating, 5 stars2 weeks ago

We are always a little hesitant about booking a room inside a host’s house, but our hosts went above and beyond! Snacks, bottled water, a fan and space heater in our room…and friendly conversation if you want it! The room and attached bathroom were extremely clean. The bed was comfortable and we were able to sleep in a quiet peaceful environment.

Top guest favorite

A swimming pool area features a stone-walled spa with a waterfall, set beside a larger pool. Light blue lounge chairs sit under an umbrella, and tall green plants provide a vibrant backdrop against the clear blue water.

Private room in Hemet

5 out of 5 average rating, 48 reviews

Private room, pool, and spa in your own paradise

SharaRating, 5 stars2 weeks ago

I felt very comfortable at John’s place. It was exactly as described. John was an amazing host, very responsive and accommodating. The pool and spa was awesome! 🤩

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Vacation rentals in Winchester

Top-rated vacation rentals in Winchester

Vacation rentals for every style

Popular amenities for Winchester vacation rentals

Other great vacation rentals in Winchester

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