
Cottage vacation rentals in Winchester
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Winchester
Guests agree: these cottages are highly rated for location, cleanliness, and more.
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!
The place was absolutely beautiful, one of the best AirBnbs we have ever stayed in, and we have stayed in a lot!! The place was decorated and furnished to a high standard and had everything you needed. The hot tub was such fun. Randy was very friendly and engaging. Would definitely recommend

Cozy cottage under the pines. With hot tub
This place was a home away from home! Overall comfortable, spacious, and clean. The house has beautiful, natural lighting and the outdoor space is gorgeous. Spa is easy to use! Would definitely stay here again!

Ranch Style home near Temecula - Las Tres Marias
We enjoyed our stay! The grandkids had a wonderful time. Would definitely come back. Great host!!

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
Beautiful area, amazing house to stay in. Very private and the animals were so fun to see. The air conditioning worked so well, all the appliances, TV and hot water/shower were great. Her instructions were very clear and easy to follow. Was able to reference them when I needed. Driving to the house was harder than I expected…the road became one way and ran into an opposite coming car that made it difficult for us to move around each other. Overall it was a unique experience!! Loved hearing the animals and peacocks!! Would stay again and would recommend!

Romantic Alpaca Retreat / Farmstay With Soaking Tu
Pet-friendly cottage rentals

Temecula Creek Cottages #2
The cabin is in a beautiful area and only 10 minutes from restaurants and shopping. The cabin is comfortable and spacious for a small space. We will definitely stay here again!!

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
The kids loved the pool and the ping pong table. All the necessities to relax for a weekend away. Front porch was great for watching sunsets. Floor to ceiling windows were awesome. AC was helpful when we needed to turn it on. Local eateries were minutes away and most were dog friendly. Such a cool little place in the mountains. Thanks for being thoughtful hosts.

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!

Temecula Creek Cottages #6
This was the perfect spot for a nice vacation! Will be coming back soon!

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.

Temecula Creek Cottages #3
We loved our quick getaway to cabin #3, peaceful and convenient!

Temecula Creek Cottages #5
Great hidden gem. Lots of very cool landscaping. Central location to lots of fun things to do.
Private cottage rentals

Midcentury Retreat - Kaiser - Parkview - CBU - UCR
easy to find parking was great with a private driveway unit was clean close to downtown didn't have any issues

Sweet Farmhouse - Kaiser - Parkview - CBU - UCR
this home was exactly as shown/described. there is designated parking on property and it was clear and easy to navigate. it was very quiet, even for being in the middle of a very busy area. there was well working A/C and I will be booking with him again

Lovely Private Studio - UCR - LLU
Overall, great place nearish to UC Riverside. I thought water pressure & temperature in the shower was perfectly fine, unlike what others mentioned in previous reviews. I have no major complaints & HIGHLY recommend this place & host! Having been an Airbnb host myself, I try to provide some suggestions for hosts to consider as well as to let future visitors be aware of. First, a coffee machine is a listed amenity, but it is a keurig style machine. I hoped for a typical coffee machine or French press so I wouldn’t have to contribute to plastic waste. Also, I noted only two k-cups in the unit. I did not see others but that was ok for me since I got free coffee at UCR. A French press would be a stellar, cheap addition. I find myself saying this for just about every host, renters are paying high priced cleaning fees. Renters shouldn’t be asked to take out trash at check out. I was surprised there were no bins in the unit for compost & recycling, especially since the former is state law now.

Riverside Studio - Kaiser - Parkview - CBU - UCR
I stayed here for a short work week. It was walking distance to the clinic so the location was perfect. I also appreciate all the amenities and parking spot.

Barn Owl Cottage ★Middle Of Wine Country★ Luxury
This place was beautiful, private, quiet and had everything we needed. The location was close to all the wineries and restaurants/shops. David and Veronika were so helpful and accommodating to our needs. The view from the upper deck was absolutely gorgeous. We got to see hummingbirds, hawks and even a rabbit came to visit . The last morning we saw a hot air balloon take off in front of our place in the valley.
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- Disneyland Park
- Oceanside City Beach
- San Clemente State Beach
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Oceanside Harbor
- San Onofre Beach
- Big Bear Alpine Zoo
- PGA WEST Nicklaus Tournament Course
- LEGOLAND California
- San Diego Zoo Safari Park
- Salt Creek Beach
- Disney California Adventure Park
- Trestles Beach
- Surf Beach
- Pechanga Resort Casino
- Honda Center
- Alpine Slide at Magic Mountain
- Moonlight Beach
- Angel Stadium of Anaheim
- Rancho Las Palmas Country Club
- Mesquite Golf & Country Club
- 1000 Steps Beach
- Palm Springs Aerial Tramway