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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

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

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

10.0 out of 10, Exceptional, (24)
"Great house with an even better backyard perfect stay"
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Blue Lagoon Oasis - Pool - Firepit - Close to Wineries
Outdoor pool

Blue Lagoon Oasis - Pool - Firepit - Close to Wineries

10.0 out of 10, Exceptional, (109)
"Best house we have rented. The host was attentive and responsive, he routinely checked with us to make sure we were good. Eric was great and approachable and I will definitely recommend this property to anyone who wants to have a 5 star experience."
Blue Lagoon Oasis - Pool - Firepit - Close to Wineries
Wolf's Creek: Hot tub, On the Creek!
Outdoor spa tub

Wolf's Creek: Hot tub, On the Creek!

9.8 out of 10, Exceptional, (25)
"My husband and I enjoyed his birthday weekend at this lovely home. The sound of the creek was relaxing and the hot tub was a welcome bonus. I would definitely stay here again."
Wolf's Creek: Hot tub, On the Creek!
20% Off May Dates - Amazing Pool, Spa,Volleyball,Views!
Pool

20% Off May Dates - Amazing Pool, Spa,Volleyball,Views!

8.8 out of 10, Excellent, (9)
"This place was so beautiful and very spacious!! Enjoyed each day!! Kids had a blast!! "
20% Off May Dates - Amazing Pool, Spa,Volleyball,Views!
❤️Amazing Ranch Temecula valley a few miles from Galway Downs equestrian center
Outdoor dining

❤️Amazing Ranch Temecula valley a few miles from Galway Downs equestrian center

9.4 out of 10, Exceptional, (34)
"The host response was impressive, the location and cleanliness of the house were great"
The price is AED 731
AED 1,347 total
includes taxes & fees
2 Jun - 3 Jun
❤️Amazing Ranch Temecula valley a few miles from Galway Downs equestrian center
1 Bed Room Casita-Suite with Private Entrance
Outdoor pool

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (40)
"Very nice neighborhood and close to shopping. Host is very communicative."
The price is AED 213
AED 510 total
includes taxes & fees
11 May - 12 May
1 Bed Room Casita-Suite with Private Entrance
15% Off May Dates- LRG Kitchen,Pool,Spa,Wineries!
Pool

15% Off May Dates- LRG Kitchen,Pool,Spa,Wineries!

9.8 out of 10, Exceptional, (43)
"Everything you could ever want if you wish to visit this area. The house is amazing and very well maintained. "
15% Off May Dates- LRG Kitchen,Pool,Spa,Wineries!
Quarter Horse by AvantStay | Countryside Retreat
Outdoor dining

Quarter Horse by AvantStay | Countryside Retreat

9.8 out of 10, Exceptional, (8)
"The size of the house. More than ample room for our family (12 people). Loved the kitchen, great rooms and layout"
Quarter Horse by AvantStay | Countryside Retreat
Wine Country Resort - Close to Wineries
Outdoor pool

Wine Country Resort - Close to Wineries

8.0 out of 10, Very Good, (1)
"Overall this was a great place to stay! Rooms were clean and spacious, pool/ backyard area is big and provides plenty of space! I would say the one downside was the spa was having difficulties heating up, however Neda was open and available to get that problem solved. I would recommend another option to get the spa heated consistently (it takes about 2 hours for it to heat up at intervals of 4 hours) and we were only able to really use it our second night after waiting for the heating. The fire...
Wine Country Resort - Close to Wineries
Walking distance to Lorimar, South Coast & Ponte Winery! Stunning Estate!
Outdoor pool, a heated pool

Walking distance to Lorimar, South Coast & Ponte Winery! Stunning Estate!

9.8 out of 10, Exceptional, (90)
"We picked this property because of its proximity to our wedding venue and wineries and capacity to hold our family. The property and grounds are immaculately maintained and we would definitely stay here again!"
Walking distance to Lorimar, South Coast & Ponte Winery! Stunning Estate!
Dove Creek Retreat - Resort Style Home, Saltwater Pool/Jacuzzi, Highspeed Wi-Fi
Terrace/patio

Dove Creek Retreat - Resort Style Home, Saltwater Pool/Jacuzzi, Highspeed Wi-Fi

9.6 out of 10, Exceptional, (4)
"We loved our stay . The house is newly renovated. Beautifully done with huge open spaces! The beds are so comfortable! Love the pool! Communication was easy and prompt. We highly recommend staying here!"
Dove Creek Retreat - Resort Style Home, Saltwater Pool/Jacuzzi, Highspeed Wi-Fi
Ultra Spacious 3000 Sqft 5-Bedroom House with Gated Yard, Garage
Aerial view

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

10.0 out of 10, Exceptional, (1)
Ultra Spacious 3000 Sqft 5-Bedroom House with Gated Yard, Garage
Lake house with hot tub, pool, game room & BBQ grill
Smart TV, fireplace

Lake house with hot tub, pool, game room & BBQ grill

9.6 out of 10, Exceptional, (5)
"Mabel was a great host, we had everything we needed at our leisure..wonderful stay!"
Lake house with hot tub, pool, game room & BBQ grill
Beverly's Hilltop Retreat
Terrace/patio

Beverly's Hilltop Retreat

10.0 out of 10, Exceptional, (11)
"This place is fantastic in every way. We loved our stay in this beautiful home! "
Beverly's Hilltop Retreat
Waterfront Lakeside Mansion Great for Large Families, Retreat, and Events
Beach

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

2.0 star property
9.6 out of 10, Exceptional, (41)
"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
15% Off May Dates - Stunning Amenities, Pool,Spa ,Views!
Pool

15% Off May Dates - Stunning Amenities, Pool,Spa ,Views!

9.4 out of 10, Exceptional, (26)
"Perfect for a 3 day getaway"
15% Off May Dates - Stunning Amenities, Pool,Spa ,Views!
Enjoy the RANCHO Villa Heart of Temecula Wine Country Golf Casinos Views RVC-023
Outdoor dining

Enjoy the RANCHO Villa Heart of Temecula Wine Country Golf Casinos Views RVC-023

10.0 out of 10, Exceptional, (93)
"The place was beautiful and the property was amazing. Everything was perfect. What else can I say. 10/10 would stay again."
Enjoy the RANCHO Villa Heart of Temecula Wine Country Golf Casinos Views RVC-023
Villa Vigna (Gorgeous Mountain View with Private Pool!)
Outdoor pool, a heated pool

Villa Vigna (Gorgeous Mountain View with Private Pool!)

9.8 out of 10, Exceptional, (60)
"Had a wonderful stay over Thanksgiving weekend. Property manager was amazing and extremely responsive to all our needs. We will stay here again! "
Villa Vigna (Gorgeous Mountain View with Private Pool!)
Fern Valley--the Perfect Spot in Idyllwild Any Time of Year
Exterior

Fern Valley--the Perfect Spot in Idyllwild Any Time of Year

10.0 out of 10, Exceptional, (394)
"Cabin was perfect. We recieved snowfall all weekend. Really enjoyed the gas fireplace and building provided puzzles. Great food and hiking nearby. Would definitely stay again. "
Fern Valley--the Perfect Spot in Idyllwild Any Time of Year
Luxury Gated Estate with Views of All of Wine Country!
Pool

Luxury Gated Estate with Views of All of Wine Country!

9.6 out of 10, Exceptional, (176)
"Beautiful property. Great location. We will definitely rent again. "
Luxury Gated Estate with Views of All of Wine Country!
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

1 Bed Room Casita-Suite with Private Entrance
Outdoor pool

1 Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (40)
"Very nice neighborhood and close to shopping. Host is very communicative."
The price is AED 213
AED 510 total
includes taxes & fees
11 May - 12 May
1 Bed Room Casita-Suite with Private Entrance
Sip and Swim Just Minutes From Temecula's Wine Country
A heated pool

Sip and Swim Just Minutes From Temecula's Wine Country

9.8 out of 10, Exceptional, (20)
"It was a great home, enjoyed our stay!"
Sip and Swim Just Minutes From Temecula's Wine Country
Chateau Vino - French Style Chalet
Exterior

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (42)
"We booked Chateau Vino to celebrate my mom’s 90th birthday. We wanted a home that fit our whole family comfortably. The house is amazing and having space to relax, eat, and enjoy the outdoors with seating for all was perfect. We had a wonderful time and hope to return again. "
Chateau Vino - French Style Chalet
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.