
Cottage vacation rentals in Winchester
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Top-rated cottage rentals in Winchester
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Romantic, private and surrounded by best Wineries!
Randy’s ranch-style guest house is close proximity to numerous wineries and is a wonderful option for a romantic weekend.

Cozy cottage under the pines. With hot tub
The cottage was amazing! Super clean, well taken care of and all around one of the best AirBnb’s we’ve been too. When we are back in Idyllwild, we will look to stay here again.

Cozy quite Cottage-near Temecula - Las Tres Marias
Place was really awesome when inside. Driving up from the outside you kind of get a weird feeling because you think it’s not what you expected. Once inside and in the backyard you know that it’s just what the pictures showed. Place was really spacious and entertaining for my family and I. The one thing that I would have loved is there’s one room that is attached to a bathroom that is locked from the entrance of the room and the bathroom that would have been awesome if it was available to us because the couch bed is a little old and not that comfortable. Other than that the pool, the slide and the jacuzzi were so much fun. One thing I suggest is maybe bringing your own pest spray because there are a lot of earwigs outside the house and in the house. Overall I would stay here in the future.

Farm Stay Bungalow And Hot Tub
The location was beautiful! The kids had fun visiting and feeding the farm animals. The glass (chickens) were very kind and provided us with delicious eggs. The host cared about our comfort and went out of their way to respond to our questions and needs. Being able to enjoy fresh citrus every day was a great plus!

Romantic Farm Stay with Hottub and View
Thank you Dawn ! This place was a blessing
Pet-friendly cottage rentals

Temecula Creek Cottages #1
I was able to book this place and stay the same day. Super easy, no hassle at all, WELL worth the price.

Downtown Riverside Boho Sanctuary
Three friends and I stayed here for a pinball tourney, place was perfect. Angel was responsive and helpful as well. He sent a new hair dryer to the place when the one there wasn’t working. Would absolutely stay here again in the future!

Country Cottage
Beautiful views. Peaceful environment. My kids LOVED getting to feed and visit the chickens daily. And my pup found some great napping spots in the sun. Great experience. Hope to visit again someday ☀️

Casita de la Maracuyá
It is difficult for me to capture exactly how ideal the Casita was for me, my husband, and our doggo on a recent trip for my beloved father's celebration of life. We had the grounds with the wild inhabitants (birds, coyote, butterflies) and the fruit trees to remind us the abundance of life, and the stars & moon with their timeless beauty to make us feel small & connected to the larger universe. Amy & Frank were welcoming, encouraged us to feel at home and were available whenever we had questions or needed anything. Their suggestions for restaurants & markets in quaint Fallbrook were spot on, but we also made good use of the fully equipped kitchen in the Casita. The peaceful, rural environment was welcome after driving around ScCal and visiting with family and friends. Walking the trails at sunset and smelling the eucalyptus was good medicine for me during an emotional time. If you believe places can hold us and keep us centered, I can tell you this one did for me.

The Cottage at Peppertree Lane Ranch
The cottage was just as described, the perfect getaway for two couples or a small family. The house had a lot of small extras that we appreciated -- snacks, waters, spices and condiments, and the bathrooms had robes, lots of towels, makeup wipes and q-tips. The beds and linens were comfy and the window coverings kept things nice and dark in the sunny mornings. The cottage is one of three houses on the property, but everything is nicely spaced out providing ample privacy. The house is a quick drive to our favorite wineries and restaurants. The hosts were helpful and fast to respond to questions. We would book this property again!

Cozy cottage with a breathtaking view
I took my daughter for a Mother/Daughter Easter get away. This was a last minute decision. We wanted a cute cottage in the middle of nowhere to decompress from our busy work and school life. Hummingbird Lodge was perfect! It was more secluded than we expected and more beautiful. We loved it!

Temecula Creek Cottages #6
Everything was as expected! Beautiful place thanks for the stay!

Looking for a nice ranch to have a great time
I stayed 2 days in July and it was super hot. The house was nice and the ranch was beautiful and clean. The owner was nice enough to let me throw my daughters first birthday there and I’m grateful. Highly recommend.
Private cottage rentals

Midcentury Retreat - Kaiser - Parkview - CBU - UCR
Great place. Private, nice , clean and perfect size for a guest or couple

Horned Owl Cottage | 5 Acre Hill Top Views | Deck
Amazing time in an Amazing place! Can't wait to come back again!

Sweet Farmhouse - Kaiser - Parkview - CBU - UCR
Definitely a great experience and pretty much no issues! There was a WiFi concern but nothing to be worried about. The only other thing was just some of the dishes not having been fully cleaned but we did it ourselves so no problem at all :))

Woodland Cottage- Mid Century Modern Beauty
The process checking in and out was smooth. The stay was peaceful. Precisely what I was looking for. The Colin’s were hospitable and polite.

Woodland View Cottage
Cabin was great. The little park within the property was great for our little on to run around while we got in a game of ping pong. The cabin had everything we needed and the hosts were very warm and friendly.

Riverside Studio - Kaiser - Parkview - CBU - UCR
The location is about a mile from my work so it was perfect for me. I was by myself and I felt comfortable and safe. I had access to the basic necessities I needed. I didn’t explore the area since I was only there for a less than a week.

Lovely Roma Cottage in Fallbrook
Our stay at the cottage was so peaceful! It was only 15 minutes to our wine tasting tour in Temecula. It was nice to feel like we were in a “home” instead of a hotel. It was tastefully furnished and very comfortable. Everything was so smooth from the moment of reservation and communication to the time we left. Would definitely come back!
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- Disneyland Park
- Oceanside City Beach
- San Clemente State Beach
- Big Bear Mountain Resort
- Marriott's Shadow Ridge Golf Club
- Bear Mountain Ski Resort
- Oceanside Harbor
- San Onofre Beach
- PGA WEST Nicklaus Tournament Course
- Big Bear Alpine Zoo
- Disney California Adventure Park
- Trestles Beach
- Salt Creek Beach
- Surf Beach
- Angel Stadium of Anaheim
- San Diego Zoo Safari Park
- Alpine Slide at Magic Mountain
- LEGOLAND California
- Chino Hills State Park
- Pechanga Resort Casino
- Honda Center
- Moonlight Beach
- McCallum Theatre
- San Onofre State Beach