Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The cabin is nestled among trees, showcasing wooden siding and multiple large decks. A vibrant sunset fills the sky, creating a warm glow across the landscape, while the surrounding foliage provides a sense of seclusion.

Cabin in Idyllwild-Pine Cove

4.96 out of 5 average rating, 179 reviews

Amazing Views & Sunsets at Paradise Pines Retreat

Mei Rating, 5 stars1 month ago

We came back from the cabin in Idyllwild and our trip was great. Cheryl is very responsive once the booking went through. Originally we included the bunkhouse in our booking but couple days before our check-in, we had some plan change. She was being very helpful and understanding though it may mean she could overpaying for the cleaning fee. I like the way how transparent our communication goes and all fair and honest. When we check in, the house is clean and very well organized and instruction are throughout the house. The playhouse is a great deal for getting our kiddos off from the screen and let their imagination grow. Also Cheryl is very flexible and helpful with check in and check out time. She is so kind and just wants to make sure we can have a great time and build good memories. Everything went very smoothly while we stayed there. We will certainly stay here again if we return to Idyllwild :)

Top guest favorite

A welcoming entrance to the cabin is illuminated by soft outdoor lighting, highlighting the rustic wooden facade and gabled roof. Two large windows frame the door, and a porch features wooden seating, all set against a serene night sky.

Cabin in Temecula

4.98 out of 5 average rating, 138 reviews

Red Cabin Ranch Temecula Wine Country

ChristinaRating, 5 stars1 week ago

Located in a beautiful grove of oak trees, with privacy and peaceful surroundings. Inside, Colleen and Wayne have thought of just about everything! We couldn’t have asked for a better long weekend. They were incredibly responsive and helpful through our stay.

Guest favorite

A spacious deck is furnished with a glass table and four cushioned chairs, surrounded by trees. Soft string lights illuminate the space, enhancing the views of distant mountains and greenery at twilight.

Cabin in Idyllwild-Pine Cove

4.94 out of 5 average rating, 127 reviews

Luxury, Private, Panoramic Views Among the Pines

LucyRating, 5 stars1 month ago

Amazing Stay – Highly Recommended. We had a fantastic stay. The check-in process was smooth. The house was clean, beautifully decorated, and equipped with all the amenities we needed for a comfortable stay. The bed was exceptionally comfortable, ensuring a great night’s sleep. The location was also perfect, stunning view from the balcony. It truly made our stay even more enjoyable. I highly recommend it to anyone looking for a comfortable, clean, and welcoming place to stay. I will definitely be returning in the future!

Guest favorite

A seating area consisting of wooden chairs is positioned atop a gently sloped hill, overlooking a vast green valley. The horizon features distant mountains under a clear blue sky, with natural vegetation and foliage surrounding the scene.

Home in Warner Springs

4.94 out of 5 average rating, 154 reviews

DESERT ROSE RANCH Mountain retreat - 360 ° views!

JeanineRating, 5 stars1 month ago

This charming two-bedroom cabin is located on the top of the hill surrounded by nature. You do need four-wheel drive if it rains or snows as it is a mile of unpaved rough dirt road up to the cabin. Once there, you are surrounded by beauty and peace. Loved star gazing at night when the weather permitted. There are neighbors who were incredibly friendly and extremely helpful. Ann’s place has everything you need to cook meals with plenty of extras. The two split unit heaters kept the house nice and comfortable even when temps dipped into the low 30’s outside. The water pressure was great in the main shower and gets incredibly hot (which I loved). My dogs enjoyed hiking around and exploring the nearby trails with me. WiFi worked great at the cabin. I cannot wait to come back and unwind again. Bring a book, laptop and some good hiking boots, this place is worth every penny spent.

Guest favorite

A tranquil garden pathway is lined with gravel and bordered by colorful desert plants. Benches are placed strategically among the lush greenery, creating inviting spots for relaxation. Sun loungers are visible in a serene area, surrounded by flowering plants and shaded by trees.

Guesthouse in Fallbrook

4.91 out of 5 average rating, 195 reviews

Cactus Garden Cottage...Best Location!!!

KimRating, 5 stars3 days ago

This beautiful location was such a blessing!! We were attending a wedding nearby and had trouble finding a location near to it. This place popped up and it was PERFECT!! Margot was so responsive and helpful to us. Her location was absolutely beautiful - and her doggies were the BEST!! One greeted us as we got out of the car. The place was spotless and perfect and had everything we needed. She was flexible with check-in as we had to be at a wedding that same day. My husband and I would stay here again in a heartbeat! Thank you so much!!

Top guest favorite

The exterior of the two-level home is illuminated by warm string lights at night, surrounded by lush trees and large boulders. Large windows showcase the interior spaces, creating a glowing ambiance that invites relaxation.

Cabin in Idyllwild-Pine Cove

4.99 out of 5 average rating, 128 reviews

Cabanon - modern luxury getaway in town

BrendanRating, 5 stars2 weeks ago

Exceptionally clean and fabulously appointed. MCM Decor was lovely. High quality and thoughtful kitchen and bathroom items. They provided coffee, popcorn, and several bathroom consumables, which was so wonderful. Lots of helpful information in the Welcome Book. The hot tub was fabulous! Probably the best part was that we only had to start the dishwasher and gather towels upon leaving, all the other cleaning was taken care of. This was the perfect long weekend location for us to relax and check out of our everyday stress. Our only dislike was that the couch and chairs in the living room while very MCM, were not terribly comfy to lounge on. Would definitely recommend staying here.

Top guest favorite

A remodeled mobile home exterior is showcased, featuring blue siding with white trim and a sloped roof design. The entrance is accessible via a set of stairs with a small porch area. Decorative stones are arranged in the front yard, complemented by low-maintenance plants and palm trees in the background.

Home in Hemet

4.95 out of 5 average rating, 183 reviews

Colonial Cottage Get-A-Way

GabrielRating, 5 stars2 days ago

Dan was very helpful and informative about surround area. Very kind and inviting, we felt at home. Will highly consider staying here again if or when visiting near. I recommend staying here if you’re looking for a comfortable and cozy stay.

Top guest favorite

A private deck is visible through wooden doors, featuring a round table adorned with potted plants and a decorative bowl. Two black chairs are positioned around the table, surrounded by tall trees providing a natural backdrop.

Guesthouse in Idyllwild-Pine Cove

4.99 out of 5 average rating, 107 reviews

Casita Ranchita Mountain Loft in Town

AnouskaRating, 5 stars1 week ago

We loved our stay in this cabin, very kitsch and well designed. Very accessible for all of idyllwild, 5min walk coffee, 15 min walk great restaurant and about 25min walk into the main town Easy to access the nearby hikes

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

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winchester

Guest favorite

Cabin in Idyllwild-Pine Cove

4.97 out of 5 average rating, 181 reviews

Rustic Luxury~Theater Room, 2 King Suites &HotTub

DavidRating, 5 stars2 weeks ago

Nice private location with gorgeous views. Shelly was extremely responsive, friendly, and helpful.

Guest favorite

A spacious outdoor area is framed by palm trees, providing shade and greenery. The driveway leads to the entrance of the house, with a small table and chairs nestled among the landscaped surroundings. Sunlight filters through the palm fronds, creating a warm ambiance.

Home in Menifee

4.92 out of 5 average rating, 254 reviews

Beautiful Family Home With Relaxing Spacious Yard

JackyRating, 5 stars1 month ago

I think she was fantastic! We just had some troubles with the doors and locks!

Superhost

A spacious bathroom features a soaking tub alongside dual sinks with modern fixtures and ample counter space. Natural light streams through a window, illuminating decorative plants. The doorway leads to a cozy bedroom area, enhancing the overall openness of the layout.

Home in Wildomar

4.77 out of 5 average rating, 30 reviews

Desert Escape: 3BD/3BA with Pool & Jacuzzi

DebraRating, 5 stars3 weeks ago

We were very happy with Dianna‘s place. We have a son that lives in Temecula so this was very convenient. Dianna was very responsive and quick to answer any questions. The only disadvantage is the traffic if you have to go into Orange County other than that, we had a wonderful time and I would highly recommend this place.

Guest favorite

A cozy outdoor seating area features a circular fire pit surrounded by modern wicker furniture with soft cushions. String lights hang above, illuminating the space. A grill is positioned nearby, with a large grassy yard providing a peaceful backdrop, ideal for evening gatherings.

Home in Rialto

4.93 out of 5 average rating, 103 reviews

Cozy modern home with huge yard!Perfect getaway!

AionaRating, 5 stars2 weeks ago

My kids and I enjoyed our weekend at Hugo’s place we felt at home very comfortable and we made some good memories there we would definitely book again in the future. It was kid friendly with building blocks, and other outdoor activities stored in the garage we enjoyed the backyard space as well.

Top guest favorite

An open living area is designed with a modern aesthetic, featuring a plush tufted sofa and a rustic wooden coffee table atop a woven rug. Large glass doors allow natural light to illuminate the space, with a view of the outdoors in the background.

Villa in Temecula

5 out of 5 average rating, 38 reviews

Villa Artemis

TiffanyRating, 5 stars1 week ago

This is by far the best Airbnb I have ever stayed in and I will for sure be coming back! Both Dr. Dimitris and the property manager, Tyler, were incredibly responsive and attentive. The house was stunning both inside and outside and we felt right at home. We all felt safe and comfortable - and we were thoroughly impressed by how well the property was taken care of. The house was clean and was full of useful amenities that made us feel right at home. Super close to our favorite wineries, but to be honest - we couldn’t wait to get back and lay by the pool. The house made our trip memorable and I cannot wait to stay here again.

Top guest favorite

A spacious property is set against a mountainous backdrop, featuring a combination of outdoor living areas and landscaped grounds. The layout includes several seating areas under shaded pergolas, with pathways leading to the main house and additional buildings.

Home in Fallbrook

5 out of 5 average rating, 13 reviews

Fab home with amenities galore!

JuliRating, 5 stars1 month ago

We had a wonderful stay! The place was spotless, cozy, and just as described. The host was attentive and made everything seamless. We truly enjoyed our time here and would love to return. Highly recommend!

Superhost

Cabin in Idyllwild-Pine Cove

4.92 out of 5 average rating, 199 reviews

Modern Cozy Cabin- Amazing Mountain Views

LorraineRating, 5 stars4 weeks ago

My family had an absolutely wonderful time here! We cooked up great meals in a kitchen that had everything we needed and the rooms were warm and cozy. The common area upstairs is filled with so much light and great views all around, we couldn't have been happier! Thank you Amy!

Superhost