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Cottage vacation rentals in Winchester

Find and book unique cottages on Airbnb

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Popular amenities for Winchester cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A wooden hot tub is situated in a serene outdoor area, surrounded by lush greenery and a private vineyard. The warm sunlight casts a gentle glow over the wooden structure, while the landscape features well-maintained paths and a spacious, natural setting.
Cottage in Temecula
4.99 out of 5 average rating, 376 reviews

Romantic, private and surrounded by best Wineries!

AngelaRating, 5 stars1 week ago
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
Top guest favorite
A charming cottage is framed by tall trees, with an inviting entrance. The green exterior of the house blends harmoniously with the surroundings, and a stone pathway leads to the front door, inviting guests to explore the tranquil setting.
Cottage in Idyllwild-Pine Cove
4.97 out of 5 average rating, 141 reviews

Cozy cottage under the pines. With hot tub

RickRating, 5 stars3 weeks ago
Beautiful location. Comfortable house. Loved the back patio. BBQ worked well. Check in and departure were easy. Just a few minutes to town.
Superhost
A vibrant outdoor space is showcased, featuring a swimming pool surrounded by lush greenery. A Jacuzzi is positioned nearby, with a shaded seating area visible under a canopy. The inviting blue water reflects sunlight, creating a relaxing atmosphere perfect for gatherings.
Cottage in Nuevo
4.93 out of 5 average rating, 28 reviews

Ranch Style home near Temecula - Las Tres Marias

StevenRating, 5 starstoday
We enjoyed our stay! The grandkids had a wonderful time. Would definitely come back. Great host!!
Superhost
A serene outdoor area features two rustic seating options positioned on a concrete patio. In the background, a red barn stands in a well-maintained garden, surrounded by green bushes and a white picket fence. The space is shaded by nearby trees.
Cottage in Fallbrook
4.9 out of 5 average rating, 98 reviews

Farm Stay Bungalow And Hot Tub

HelenRating, 5 stars4 months ago
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!
Guest favorite
A welcoming deck is equipped with several colorful outdoor chairs arranged around a central table. Lush greenery and rolling hills are visible in the background, creating a serene and natural setting.
Cottage in Fallbrook
4.95 out of 5 average rating, 264 reviews

Romantic Farm Stay with Hottub and View

JenniferRating, 5 stars1 month ago
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 in Redlands
4.58 out of 5 average rating, 12 reviews

Cottage at the Historic Morey House

DamianRating, 5 stars25 months ago
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
Superhost
A fluffy llama is seen approaching the hand of a person outside a fenced area. The animal's curly coat reflects the sunlight, highlighting its distinctive features. The background is filled with natural vegetation, contributing to the serene farmhouse atmosphere.
Cottage in Fallbrook

Romantic Alpaca Retreat / Farmstay With Soaking Tu

Pet-friendly cottage rentals

Superhost
A charming cottage is set against a backdrop of lush greenery and large boulders. A wide staircase leads to a welcoming front porch, which is bordered by white railings and adorned with hanging plants. Tropical palm trees frame the scene, enhancing the tranquil setting.
Cottage in Temecula
4.85 out of 5 average rating, 560 reviews

Temecula Creek Cottages #1

BrittynRating, 5 stars3 weeks ago
I had such a wonderful stay! The cottage was clean and welcoming and i really enjoyed the beautiful landscape. I would absolutely recommend this place and look forward to staying here again in the future.
Guest favorite
A charming cottage is nestled among lush greenery and tiered granite hills. The exterior features a welcoming front porch with a wooden chair. Surrounding the cottage, a rustic stone wall adds character, while flowering plants create a vibrant touch against the natural backdrop.
Cottage in Temecula
4.85 out of 5 average rating, 571 reviews

Temecula Creek Cottages #2

BriRating, 5 stars2 weeks ago
Beautiful location! Super close to shops and eating yet felt secluded. The grounds were very well kept and the place was nice. Perfect getaway! We had trouble with the door locking, but Damien took care of this as soon as he could and was responsive and helpful and all worked out great! Would visit again.
Superhost
A modern cottage is nestled among tall trees, featuring large glass windows that allow natural light to fill the interior. A wooden deck is visible in the foreground, with a few outdoor seating chairs arranged for relaxation.
Cottage in Idyllwild-Pine Cove
4.89 out of 5 average rating, 18 reviews

Woodland View Cottage

LaurenRating, 5 stars4 months ago
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.
A bright living area is showcased, featuring a light-colored sofa adorned with decorative pillows. A round mirror hangs on the peach-colored wall, reflecting natural light. A television is mounted above a wooden cabinet, and a small potted plant adds greenery to the space.
Cottage in Downtown Riverside
4.71 out of 5 average rating, 24 reviews

Downtown Riverside Boho Sanctuary

AndyRating, 5 stars4 months ago
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!
Guest favorite
The cottage exterior showcases a welcoming yellow facade framed by lush greenery and vibrant flowers. Two wrought-iron chairs and a small table are positioned near large windows, inviting guests to enjoy the tranquil garden surroundings.
Cottage in Fallbrook
4.93 out of 5 average rating, 130 reviews

Country Cottage

AshleeRating, 5 stars1 week ago
The property was absolutely gorgeous, and the cottage was very peaceful. Even though the cottage is on the main property, it is private from the main house. It was a great place for dogs to explore, and they loved looking at the chickens. Host was kind and extremely helpful.
Guest favorite
A cornhole board is positioned on a sandy surface, featuring the name 'Peppertree Ranch'. Colorful bean bags in purple and red are arranged for play. In the background, a farmhouse with a porch is visible, surrounded by trees and open space.
Cottage in Temecula
4.95 out of 5 average rating, 64 reviews

The Cottage at Peppertree Lane Ranch

StellaRating, 5 stars8 months ago
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!
Superhost
A spacious wooden deck extends outwards, offering unobstructed views of the surrounding hills. The area is adorned with several hummingbird feeders and a comfortable seating arrangement, complemented by potted plants, creating a serene environment for relaxation.
Cottage in Fallbrook
4.74 out of 5 average rating, 133 reviews

Cozy cottage with a breathtaking view

LeneRating, 5 stars2 weeks ago
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.
Superhost
An inviting cottage exterior is framed by natural stone and wooden accents, showcasing a white picket fence. A spacious deck features picnic tables and seating arrangements, surrounded by lush greenery and oak trees, creating a serene outdoor atmosphere.
Cottage in Temecula
4.86 out of 5 average rating, 554 reviews

Temecula Creek Cottages #6

JacquelineRating, 5 stars3 weeks ago
This cottage was just as described, had everything we needed and was close to all the wineries and old town Temecula. Would definitely come back!

Private cottage rentals

The exterior of the cottage is highlighted by a welcoming blue front door, flanked by two chairs in vibrant blue. Lush greenery and trees surround the entrance, creating a cozy atmosphere. A small porch offers a space to relax before entering the home.
Cottage in Riverside
4.73 out of 5 average rating, 97 reviews

Midcentury Retreat - Kaiser - Parkview - CBU - UCR

SandraRating, 5 stars3 weeks ago
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!
A cozy corner of the studio features a black metal bed with white linens. Next to it stands a vintage nightstand with two drawers, accompanied by a small plant. A decorative windmill piece is mounted on the wall above, with sunlight filtering through sheer curtains.
Cottage in Riverside
4.85 out of 5 average rating, 155 reviews

Sweet Farmhouse - Kaiser - Parkview - CBU - UCR

LeilaRating, 5 stars1 month ago
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
Top guest favorite
Cottage in Silverado
5 out of 5 average rating, 21 reviews

Enchanting Artist Forest Retreat

LaniRating, 5 stars3 weeks ago
We had a wonderful stay at this charming cottage—it was the perfect spot for a peaceful and relaxing getaway. The location was ideal, with plenty of things to do nearby. We went wine tasting at Giracci Vineyards, enjoyed a delicious dinner at Xacalli Kitchen, and went hiking at Maple Springs! The cottage itself was cozy, clean, and well-equipped. We especially loved that we could cook and bbq dinner outside during our stay. Communication with our host was seamless; she was incredibly sweet and responsive throughout our visit. Meeting her adorable Maltese was truly the highlight of the trip! Highly recommend this cottage; We’ll definitely be back!
Superhost
The exterior of a modern cottage is framed by tall pines and cedars, featuring large floor-to-ceiling windows that reveal a well-lit interior. A wooden deck extends from the entrance, complemented by simple outdoor seating, creating a seamless connection with the surrounding natural landscape.
Cottage in Idyllwild-Pine Cove
4.91 out of 5 average rating, 44 reviews

Woodland Cottage- Mid Century Modern Beauty

Lilliana HuertaRating, 5 stars5 months ago
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.
A baking sheet is displayed inside a wooden drawer. The baking sheet is dark gray with a product label showing images of baked goods. The drawer is clean and appears to be part of the kitchen cabinetry.
Cottage in Riverside
4.67 out of 5 average rating, 18 reviews

Lovely Private Studio - UCR - LLU

MichaelRating, 5 stars12 months ago
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.
A small workspace is positioned against a wall, featuring a white table accompanied by two black metal chairs. A decorative green wall art piece, resembling a vertical garden with various plants, adds a refreshing touch above the table. A stylish trash can stands nearby.
Cottage in Riverside
4.94 out of 5 average rating, 162 reviews

Riverside Studio - Kaiser - Parkview - CBU - UCR

LanaRating, 5 stars1 month ago
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.
Guest favorite
A kitchen countertop displays a Keurig coffee maker and a white microwave, set against a patterned granite surface. Two wooden bowls rest above the microwave, adding a touch of natural decor to the space.
Cottage in Fallbrook
4.95 out of 5 average rating, 21 reviews

Cutest Cottage "The Sunflower House"

RyanRating, 5 stars2 weeks ago
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
Guest favorite
A landscaped pathway of large stone slabs leads through a gravel area toward the exterior of a Tuscan-style villa. Flanking the path, manicured greenery and flowering plants offer a serene setting. The villa's stucco walls and terracotta roof are complemented by a decorative stone fountain in the background.
Cottage in Fallbrook
5 out of 5 average rating, 7 reviews

Lovely Roma Cottage in Fallbrook

JillRating, 5 stars4 months ago
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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