
Cottage holiday rentals in Winchester
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Top-rated cottage rentals in Winchester
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Holiday rentals for every style
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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
Beautiful location. Comfortable house. Loved the back patio. BBQ worked well. Check in and departure were easy. Just a few minutes to town.

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!

Cottage at the Historic Morey House
Absolutely loved our stay at Pennys place. Hopefully we’re blessed enough to be able to stay again. Stunning views and perfectly peaceful!!!! 10/10 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!

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
Very cute little rustic place off the beaten path. Enjoyed the evenings on the deck. Beautiful views. Our dogs loved chasing the birds and the lizards.

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.
Private cottage rentals

Cutest Cottage "The Sunflower House"
Great place on the Gourd Farm. Super cute. Cabin was well furnished/updated. Very clean! Host was very accommodating and even left farm fresh eggs on our doorstep in the morning. 10/10 5 stats for sure

Midcentury Retreat - Kaiser - Parkview - CBU - UCR
This place was exactly how it was described and made it feel completely like I was at home for myself and my friend who stayed with me. Super comfortable loved the shower and the closeness of where everything is at was amazing!

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

"theBedroom" Bed & Bath is a Elegant Cozy Oasis.
Dorothy’s place was amazing, my friend and I stayed there for Beyond Wonderland and had the most amazing time! The place is very clean and private, we love the little details that Dorothy adds! 10/10 would come here again thank you for having us!

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.

Cottage - 5min Walk to Beach, Garden & Fireplace
Leah’s place was a great little getaway. We stayed 4 nights. San Clemente Pier was so close once you walked the 5 minutes to Linda Lane Park & Beach area. The walk to the beach was downhill, so uphill on the way back, but we enjoyed the steps:). (Note: home on one way street) We had to be a little more aware of one another with one bathroom. I especially enjoyed the stackable washer/dryer in the kitchen. I was impressed with how little space they took up, yet washed and dried beautifully. The decor and art pieces were perfect for a beach retreat vibe. My kids enjoyed the amenities supplied in the garage, including bodyboards, surfboards, beach toys and 2 bikes. Even wetsuits, which my daughter was able to wear while surfing and my son used another day just playing in the ocean. The garage was nice to be able to park in as well. We had a lovely time at Leah’s place and the property itself was well maintained with gorgeous vegetation. It felt comfy and cozy and had all we needed.

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