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House holiday rentals in Winchester

Find and book unique houses on Airbnb

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Popular amenities for Winchester house rentals

House rentals with a pool

Guest favourite
Home in Lake Elsinore
4.88 out of 5 average rating, 212 reviews

Secluded Large Country Ranch Estate

ElenaRating, 5 stars2 weeks ago
I get my adult children together once a year. My daughter, her husband and toddler come from Washington. We really enjoyed our stay at the Lake Elsinore home. David, the host was very nice. The home has everything you need. The kitchen is very well equipped. They had enough beds, towels and everything you could think of was there. My grandson had a lot of fun in the back yard, they thought of everyone when they made this home an Airbnb. I was very pleased. Although the pool wasn’t heated as expected, David did everything in his power to make it happen. I absolutely appreciated all he did and we all enjoyed our stay. My daughter asked if we could do it at the Elsinore house next year again. Thanks again David!!!
Superhost
Home in Temecula
4.9 out of 5 average rating, 134 reviews

The Peaceful Family Farmhouse(5 min to wineries)

RichRating, 5 stars2 weeks ago
This place was perfect for our family!! We were in town for our son's wedding, and this place was an excellent fit! Clean, roomy, full of amenities and lots to do! The location was perfect, as it's close to wedding venues and many wineries. Also, only about 15min drive to old town. Hosts have excellent communication practices, very responsive to questions, provided great information about the house, and offered many suggestions for local venues. They even went out of their way to film short videos of nearby venues for us to host a rehearsal dinner. Excellent service! Thanks for making the stay memorable! Cheers!
Superhost
Home in Temecula
4.86 out of 5 average rating, 262 reviews

Caballos Manor - Beautiful Wine Country View Home

EdwardRating, 5 stars4 weeks ago
Great location and space!
Superhost
Home in Temecula
4.88 out of 5 average rating, 191 reviews

Resort pool w/waterfall slide,steps from wineries!

AndiRating, 5 stars1 week ago
Great stay overall. Lisa was very friendly. We arrived 1.5 hours early while the house was still being cleaned, and she let us wait at the pool. I had left my glasses behind and she is arranging for them to be mailed to me. The pool is perfect for our 2 young kids given the large shallow area. The house is spacious and has everything we needed. It is a short ride to many wineries, and within 10 minute drive to stores. Everything was cleaned before we checked in and in great working order. Would definitely stay here again!
Guest favourite
Home in Riverside
4.91 out of 5 average rating, 124 reviews

Summer Oasis: Tropical Vibes + Pool & Mini Golf!

OmarRating, 5 stars3 weeks ago
Everything was as described. Worked perfect for us.
Guest favourite
Home in Riverside
4.96 out of 5 average rating, 112 reviews

CHARMING POOL HOME BY DOWNTOWN *FAMILY GETAWAYS*

JoseRating, 5 stars1 week ago
My family and I stayed in this Airbnb and we had an amazing time! Everything was amazing. We appreciate how organized the house was. The pool was fantastic my family and I enjoyed every minute about staying at this Airbnb. The beds were comfy and had everything we needed! I will definitely be back again ❤️❤️❤️❤️❤️
Superhost
Home in Riverside
4.79 out of 5 average rating, 184 reviews

Mid Century Modern POOL HOME w/ GAME ROOM

LazaroRating, 5 stars2 weeks ago
Awesome time with the family, well worth it
Superhost
Home in Temecula
4.86 out of 5 average rating, 112 reviews

Wine Country Heaven Surrounded by Vineyards!!

GabrielleRating, 5 stars1 month ago
Our family had an AMAZING time here! We truly could not have found a better spot. The backyard is incredible, full of so much charm and had beautiful views! The pool is wonderful and so refreshing (we opted to heat it and glad we did as it was ideal for swimming in the morning and evenings as well). There is also a covered cabana area with chairs and a fireplace - this was a great place to duck out of the heat for a bit, to chat and play cards and relax. They even have a fun game room where my kids played pool (you can also play ping pong). The bar/grill area is pretty big with additional seating and also has a tv (which my husband loved so he could grill and watch golf ;) This place had it all! We truly had a fantastic time here and Justin was amazing as well - he was super responsive and answered all of our questions very quickly. Great host, great place - it was perfect! We had an awesome time and would love to come back again soon!

Weekly house rentals

Guest favourite
Home in Temecula
5 out of 5 average rating, 17 reviews

New - VIEWS, Spa, Game Room, Minutes To Wineries

ChabellysRating, 5 stars1 week ago
Absolutely loved our stay! The home was immaculate, incredibly comfortable, and nestled in the heart of wine country with stunning views. The host was super responsive and made everything seamless. A perfect getaway—highly recommend wish I could have stayed longer. Short 20 min drive to the main stores so if you arrive early get your groceries first. Small dirt road driveway no biggie we had an SUV. Apple Maps took us directly north issues finding the location.
Top Guest favourite
Home in San Jacinto
5 out of 5 average rating, 21 reviews

Casa Isabel

DeniseRating, 5 stars2 weeks ago
This is our second visit to Mariela's place. It is a great location for us during my work trips to Hemet. It is so much better than staying at a hotel. We are very comfortable at the house and have everything we need. I expect we'll be back in the Fall. We did take a weekend drive to BigBear and enjoyed that trip. Thank you!
Superhost
Home in Winchester
4.87 out of 5 average rating, 93 reviews

Temecula Wine Country Oasis Experience/Game Room

PhyllisRating, 5 starstoday
Our stay at Edgar’s place was amazing! The highlight for us was the fully stocked kitchen it had everything we needed for a comfortable and convenient stay. The whole group loved the spacious layout of the house, and the pool was a big hit with everyone. Highly recommend! We’re already planning for our next stay!
Guest favourite
Home in Hemet
4.86 out of 5 average rating, 28 reviews

Hemet Haven |Jacuzzi|Pool|Game Room|BBQ|King S Bed

BrianRating, 5 stars2 weeks ago
We enjoyed our stay - close to all of our planned activities- easy to find, kids loved the pool! Clean, quiet, comfortable.
Guest favourite
Home in Winchester
5 out of 5 average rating, 12 reviews

Wine country 4 bedroom, game room and chalk wall.

VanessaRating, 5 stars4 days ago
Amber and Jacob were great hosts. The Airbnb had everything we needed and plenty of beds.
Top Guest favourite
Home in Menifee
4.95 out of 5 average rating, 86 reviews

Brand new home/close to wineries

FernandoRating, 5 stars4 weeks ago
I recently stayed at Victoria Place for a 3-day tournament with my son and family , and it felt just like home. The location is fantastic, situated near a shopping center with groceries and various food spots within walking distance. The neighborhood is quiet and peaceful, making it an ideal retreat after our busy days. Communication with Victoria was excellent; she responded quickly and provided detailed instructions for check-in and check-out, which made the whole experience seamless. I will definitely be staying here again on our next visit. Highly recommend!
Top Guest favourite
Home in Murrieta
5 out of 5 average rating, 9 reviews

~NEW~Insurance•Claim•Welcome~Pool•SPA•Billiards!

KellyRating, 5 stars6 months ago
Chose this location for holiday family gathering for rooms and entertainment factor and it did not disappoint. Lots of space to socialize, watch the big game, shoot some pool, and splash in the jacuzzi! Family loved playing some blackjack and cornhole too. I want to go back already! Host was so responsive and helpful on every level. Neighborhood was safe, quiet, and backyard was very private too. Don’t wait to book this lovely home, reserve for your vacay today!
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 44 reviews

Pool Paradise near Temecula wineries w/ spa/games

Klaudia MaeRating, 5 stars4 days ago
We had a fantastic time at this Airbnb! The space was clean, comfortable, and had everything we needed for a relaxing getaway. The guide provided with local things to do was super helpful and led us to some great hidden gems in the area. We especially loved the grill area and spent lots of time enjoying the pool. It was the perfect setup for both fun and relaxation. Highly recommend this place for anyone looking for a memorable stay!

Private house rentals

Top Guest favourite
Home in Murrieta
4.94 out of 5 average rating, 34 reviews

Dove Creek Retreat | Chef's Kitchen & King Beds

JessicaRating, 5 stars4 weeks ago
We had a wonderful stay! The house was beautiful—clean, spacious, and located in a quiet, peaceful neighborhood. Our host was incredibly responsive and always available to help, especially with the hot tub, which made our stay even more relaxing. Would definitely recommend and would love to stay again!
Guest favourite
Home in San Jacinto
4.76 out of 5 average rating, 25 reviews

Modern Family Oasis

AnitraRating, 5 stars1 day ago
Our stay at the Oasis was rated top tier. My daughter didn't want to leave. The home was beautiful and provided plenty of activities for the entire family. They were extremely helpful and very responsive. I will definitely book this location again and again and again!
Top Guest favourite
Home in Temecula
5 out of 5 average rating, 11 reviews

Your Wine Country Getaway Awaits!

AllisonRating, 5 starstoday
We thoroughly enjoyed our stay at Paul’s place and were all in agreement that it was our favorite Airbnb we’ve rented and the most well appointed. Paul has thought of everything you could possibly need and more. The place was pristinely clean and we enjoyed the outdoor space as well. It’s a very short drive to the wineries. Would highly recommend!
Top Guest favourite
Home in Riverside
5 out of 5 average rating, 19 reviews

Golden Hour Oasis~MovieTheater~Hot Tub

AndrewRating, 5 stars2 weeks ago
This place is a beautiful oasis! The back yard is perfect for spending a whole day or evening, swimming, sun bathing, grilling burgers and hanging out with the family!
Guest favourite
Home in Murrieta
4.96 out of 5 average rating, 79 reviews

Casa Escondido Horse Ranch.

DanielleRating, 5 stars1 month ago
Christopher’s home was a perfect getaway for myself and my family! Only one tv, but we were too busy cooking and talking to even use it! The outside surroundings were gorgeous! So peaceful and quiet. We walked around a bit and came across one of the dogs on the property. Such a sweet girl who guided us back up to the house. We were not able to use the outside seating couches as there were dirt marks and paw prints all over lol. Dogs clearly love it. This didn’t bother us at all but putting it out there for those who like to sit outside. The house was perfectly clean! Beautiful open kitchen and lots of amenities. It is pretty far from Temecula. Took us about 50 minutes on a Saturday morning to arrive in Temecula. Granted it was Memorial Day Weekend. We appreciated the wine bottle for us too! Just lovely personal touches in this home. We definitely plan to stay again. We missed the tour of the animals but hope to do it soon.
Superhost
Home in Hemet
4.84 out of 5 average rating, 43 reviews

Peaceful & Cozy 3 bedroom Ranch-Home w/Fireplace

CarrieRating, 5 stars1 month ago
Patrick was a great host. Clear instructions and checked to make sure our stay was going well. Even offered to bring by some fresh eggs…basically gold these days. Location was perfect for Nationals at K1 Circuit. We enjoyed the pool table and foosball in the garage. The coffee bar was a nice touch. The house matches the description and pictures, so nothing fancy, but good value and perfect for what we needed. Bonus of comfortable beds. Overall excellent stay.
Superhost
Home in Murrieta
4.85 out of 5 average rating, 68 reviews

Peaceful Temecula Valley | Pool, Hot Tub, and Pets

TriciaRating, 5 stars1 week ago
We had a wonderful stay, house is clean and had everything we needed. Backyard and pool are lovely, we were able to relax and spend time with family. Would definitely rent again.
Guest favourite
Home in Temecula
4.91 out of 5 average rating, 53 reviews

Summit Ranch by AvantStay | Infinity Pool + Views

LauraRating, 5 stars4 days ago
Our stay was absolutely perfect!! The location was great and remote which made it feel like we were somewhere completely far away. Our girls loved the pool, our dog loved exploring, and the timely response to questions asked was appreciated. The only thing that we would have liked is to have a heads up of maintenance work. We arrived on Monday and immediately jumped in the pool. On Tuesday, our goal was to be out in the pool earlier but the gardeners showed up. On Wednesday, it was the pool guy. On Thursday it was back to gardeners for tree trimming. As homeowners ourselves, we understand that these maintenance visits are necessary and maybe all three full days had someone there because it was part of the schedule but either plan accordingly for when guest are not around OR give the guests a heads up so they know what to expect. With that said, none of that dampened our experience, simply, it would have been nice to know ahead of time. Would definitely visit again and recommend!

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