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Check prices for these dates

Compare 755 Vacation Homes in Winchester with updated reviews, rates, and availability.

20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

8.4 out of 10, Very Good, (7)
"Overall, everything was good. The house is lacking a few essential items (like oven mits and cleaning spray to wipe down counters) but it worked great for our large group. Location was more remote than expected, but it was absolutely beautiful. Ran into a few minor issues during our stay but always received a timely response from the property manager in a professional manner."
20% Off Mar - Amazing Pool, Spa,Volleyball,Views!

❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

9.2 out of 10, Wonderful, (30)
"Needed to book a house for my friends wedding. House was perfect lots of room very clean. Beautiful views we all had a good timeWould book again "
The price is SAR 938
SAR 1,619 total
includes taxes & fees
26 Mar - 27 Mar
❤️Amazing Entire Ranch Home in Temecula valley wine country! ❤️

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (39)
"Perfect for a quick overnight stay. "
The price is SAR 218
SAR 502 total
includes taxes & fees
24 Mar - 25 Mar
1/Bed Room Casita-Suite with Private Entrance

Fallbrook Tuscan villa oasis!

9.8 out of 10, Exceptional, (112)
"with the tall Italian cedars. It does feel much like a villa amongst the rolling Hills and Vineyards of this area north north east of San Diego, this property is very spacious.We picked it because we were five siblings in each one could have their own bedroom.(our aunt was turning 100 so he flew down to celebrate) The master bedroom with the incredibly huge master bath with a remarkable built in Jacuzzi bath was something else.Our host Denise was very communicative making sure that we could heat...
Fallbrook Tuscan villa oasis!

Perfect 4 Families- LRG Kitchen,Pool,Spa,Wineries!

9.8 out of 10, Exceptional, (40)
"This place was great! It had a wonderful layout that accommodated our group perfectly. It was in a very quiet area with easy access to wineries. The only thing that could have improved our stay was if the jacuzzi was taken care of better. You could tell it had been a while since chemical had been added or that it had been cleaned. I made my son take a shower every time he got out otherwise he got itchy.Overall, I highly recommend this place!"
Perfect 4 Families- LRG Kitchen,Pool,Spa,Wineries!

Blue Lagoon Oasis - Pool - Firepit - Close to Wineries

10.0 out of 10, Exceptional, (107)
"We enjoyed our stay at Casa Vino. We came to Temecula to celebrate my husband’s 50th birthday with our kids & grandkids. House was spacious & cozy for our little family. Beds were comfortable. Eric responded to my messages promptly. House is close by stores and not too far from the golf course & wineries. Highly recommend. "
Blue Lagoon Oasis - Pool - Firepit - Close to Wineries

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (17)
"This was by far one of the best places I've stayed. Everything was exceptional! Little touches like water bottles, toothbrushes (in case you forgot yours) to cereal, coffee, real cream, wine and other goodies. The pool and hot tub were beautiful and easy to turn on. Fun games and plenty of room for the 6 of us on a girl's wine tasting birthday weekend. Highly, highly recommend. Beds were very comfortable (pillows were a little hard so if you want soft pillows you might want to bring your own)...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

Charming Hill Top Wine Country Villa- Minutes to all Vineyards

9.8 out of 10, Exceptional, (75)
"Convenient and quiet location. Perfect for our girls weekend away!"
Charming Hill Top Wine Country Villa- Minutes to all Vineyards

Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

2.0 star property
9.6 out of 10, Exceptional, (40)
"We had an amazing experience at this property. The space was enormous and regal, offering the perfect setting for our event. The view of the lake, especially during the sunrise, was breathless! The property manager, Daniel, was incredibly responsive and helpful, promptly answering our numerous questions. The highlight of the experience was Daniel's outstanding assistance when we accidentally left a bag behind—he went above and beyond to ensure we got it back. We had a fantastic time and highly...
Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events

20% Off Mar Dates-Stunning Tuscan Retreat,Pool/Spa!

9.0 out of 10, Wonderful, (22)
"Sunny Days was very responsive and took care of us. Temecula Rose was the great home away from home for the bachelorette weekend. Thank you!"
20% Off Mar Dates-Stunning Tuscan Retreat,Pool/Spa!

4 Bedroom Home Just Minutes From Wine Country

10.0 out of 10, Exceptional, (32)
"We stayed at this property for 5 days. The host was very accommodating and always kept a clear line of communication. The property is nice and well kept. The family was happy and we look forward to visiting again."
4 Bedroom Home Just Minutes From Wine Country

La Petite - Center of town - Beautiful Remodel

9.8 out of 10, Exceptional, (9)
"The place was so cute and it snowed when we visited which made it so magical! The host was also very communicative. "
The price is SAR 349
SAR 1,592 total
includes taxes & fees
24 Mar - 25 Mar
La Petite - Center of town - Beautiful Remodel

Ultra Spacious 3000 Sqft 5-Bedroom House with Gated Yard, Garage

10.0 out of 10, Exceptional, (1)
The price is SAR 506
SAR 1,510 total
includes taxes & fees
24 Mar - 25 Mar
Ultra Spacious 3000 Sqft 5-Bedroom House with Gated Yard, Garage

Charming Winchester Guesthouse near Wine Country

9.8 out of 10, Exceptional, (6)
"It was a pleasant experience (ranch vibe)"
Charming Winchester Guesthouse near Wine Country

Beverly's Hilltop Retreat

10.0 out of 10, Exceptional, (7)
"This place is fantastic in every way. We loved our stay in this beautiful home! "
Beverly's Hilltop Retreat

Wine Country Resort - Close to Wineries

Wine Country Resort - Close to Wineries

7 BR/5.5 bath PERMITTED TEMECULA WINE COUNTRY VACATION RENTAL

10.0 out of 10, Exceptional, (34)
"I rented the property for my birthday party and the house was awesome! Beautiful sunsets and sunrise views plus all amenities you can ask for!"
7 BR/5.5 bath PERMITTED TEMECULA WINE COUNTRY VACATION RENTAL

House with pool/spa/minutes to wineries

8.6 out of 10, Excellent, (26)
"The host was vey attentive and helpful. A great place to stay. "
The price is SAR 1,678
SAR 4,144 total
includes taxes & fees
24 Mar - 25 Mar
House with pool/spa/minutes to wineries

Villa Vigna (Gorgeous Mountain View with Private Pool!)

9.8 out of 10, Exceptional, (60)
"We returned gor our 2nd time to this beautifulProperty. We celebrated our dads 80 th birthday. Beautiful property very clean very convenient close to the wineries. The owner was very helpful and great communication. The check-in process was easy. Will come back again soon."
Villa Vigna (Gorgeous Mountain View with Private Pool!)

Home on Organic Farm Near Wine Country and Casinos

9.4 out of 10, Exceptional, (33)
"Place was exactly what we were looking for. It’s quite a ways out in the hills but if that’s what you are looking for then this is the place. "
Home on Organic Farm Near Wine Country and Casinos
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winchester

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (38)
"The house itself is lovely—well-kept, nicely furnished, and comfortable for a group. Unfortunately, there was a fairly large leak in the living room due to heavy rain right as we checked in. That said, the homeowner responded quickly and handled it to our satisfaction.A couple things to keep in mind: the bunk room doesn’t have a nearby bathroom, so anyone staying there will need to go through another bedroom to shower. It’s manageable, just not the most convenient setup.We also received a...
Chateau Vino - French Style Chalet

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (17)
"This was by far one of the best places I've stayed. Everything was exceptional! Little touches like water bottles, toothbrushes (in case you forgot yours) to cereal, coffee, real cream, wine and other goodies. The pool and hot tub were beautiful and easy to turn on. Fun games and plenty of room for the 6 of us on a girl's wine tasting birthday weekend. Highly, highly recommend. Beds were very comfortable (pillows were a little hard so if you want soft pillows you might want to bring your own)...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (39)
"Perfect for a quick overnight stay. "
The price is SAR 218
SAR 502 total
includes taxes & fees
24 Mar - 25 Mar
1/Bed Room Casita-Suite with Private Entrance
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.