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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Exterior
Chateau Vino - French Style Chalet
10.0 out of 10, Exceptional, (29)
"We had a large group gathering here to celebrate my husband’s birthday. The house was perfect and the communication and property management was incredible. We were thankful for such a great place to spend time together!"
Chateau Vino - French Style Chalet
Terrace/patio
Wine Country Oasis Retreat - Close to wineries
10.0 out of 10, Exceptional, (32)
"I took a trip with 9 of my girlfriends and we were absolutely spoiled by this VRBO! The hosts were accommodating, quick communicators, provided the little details (toothpaste, little soaps, lots of pool towels, etc) and went above and beyond for us. After a quick text to the host, the hot tub was on and ready for us! 10/10 experience, would recommend!!"
Wine Country Oasis Retreat - Close to wineries
Property grounds
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
10.0 out of 10, Exceptional, (21)
"Enjoyed the mornings on the porch listening to the close by creek and chickadees singing, hiked every day, used the grill on the side of the house, walked around the neighborhood in admiration. We brought our dog (golden retriever) and he was so happy there as well. Close to town but also not TOO close. Loved this cabin!! Would stay again."
The price is $113
$229 total
includes taxes & fees
Jun 4 - Jun 5
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
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A heated pool
The most luxurious and sought-after Short-Term Rental in Wine Country.
10.0 out of 10, Exceptional, (9)
"My wife and I were looking for a high end place to celebrate our 70th birthday with our kids and grandkids. We saw Villa Fabulosa on the VRBO sight and instantly knew this was it. All the reviews and pictures were amazing but fell short of the reality.This fantastic property is jaw dropping.EVERTHING is provided and EVERYTHING is first class.Big things like appliances, stove oven,two dishwashers,two washer dryers,BBQs,flat top grill,ice machines inside and out. mall items like...
The price is $1,793
$3,167 total
includes taxes & fees
May 23 - May 24
The most luxurious and sought-after Short-Term Rental in Wine Country.
Outdoor pool, a heated pool
A premier rental estate with an ample array of amenities & outdoor lounge areas
10.0 out of 10, Exceptional, (171)
"Our nephew was getting married at the Ethereal Gardens in Escondido. So, we needed a location that could fit our family of 10-14 and be close to the venue. It was so nice to come back to the house to relax after events. The backyard was absolutely stunning with plenty of activities for all (ping pong, foosball, basketball ball court, min golf, bbq, pizza oven, fire pits + more!). They were available to help with anything we needed (they live on property) and were hospitable and friendly. As...
A premier rental estate with an ample array of amenities & outdoor lounge areas
Exterior
The Wine Away-Large Home w/Jacuzzi
10.0 out of 10, Exceptional, (13)
"We hosted our mastermind event The Abundance Retreat here, for leaders in alternative health & wealth. It was the perfect location! Communicated abundance while soaked in glorious nature. Barefoot Rentals was excellent to work with, even allowing us to do a site visit prior to the event itself. Would definitely come back! Thank you again for such a memorable experience!!"
The Wine Away-Large Home w/Jacuzzi
Fridge, microwave, oven, stovetop
Modern Spacious home in Murrieta near Temecula wineries and Historic Old Town
10.0 out of 10, Exceptional, (14)
"Laura was a great communicator before, during and after our trip. Very nice spacious house in a quiet neighborhood very close to Temecula."
The price is $277
$425 total
includes taxes & fees
May 22 - May 23
Modern Spacious home in Murrieta near Temecula wineries and Historic Old Town
TV, fireplace, DVD player, books
Secluded Dog-Friendly Cabin w/Wood Fireplace, Deck, Private W/D, Mtn Views
10.0 out of 10, Exceptional, (42)
"We had a wonderful time at Elk Horn Retreat. We stayed 5 nights and loved every minute of it. The cabin is beautifully decorated, well furnished, and extremely comfortable. The location is very private and an easy drive to town. Highly recommend this cabin for a stay in Idyllwild."
Secluded Dog-Friendly Cabin w/Wood Fireplace, Deck, Private W/D, Mtn Views
Game room
Hill Top Estate In The Heart Of The Wine Country W/incredible Views!!
10.0 out of 10, Exceptional, (86)
"My extended family of 12 adults stayed here from 4/23-4/29/2024 for my niece’s wedding in Temecula. The breathtaking views were spectacular as were 10-12 hot-air balloons which we saw! Our property manager, John, was amazing to work with. His quick responses to my daily inquiries were appreciated. However, the place definitely needs sprucing up with TLC. As the week went on, I could see previous damages made to this place. We heated the jacuzzi for a few hours each day because it was much less...
Hill Top Estate In The Heart Of The Wine Country W/incredible Views!!
Exterior
Fern Valley--Fresh New Snow--Crazy in April!
10.0 out of 10, Exceptional, (360)
"I spent a wonderful long weekend in this Fern Valley house. The neighborhood is very quiet, I enjoyed listening to bird songs, the house is all surrounded by beautiful trees. The house itself is very clean and comfortable. A great living room for relaxing and reading. A full kitchen for making your own meals if you feel like it. Bedrooms and bathrooms are very nicely decorated and very comfortable. Squirrels and a big blue Steller’s jay come to the deck if you leave some treats out. And of...
Fern Valley--Fresh New Snow--Crazy in April!
Pool | Outdoor pool, a heated pool
Mansion on De Portola with Vineyard and Mountain view
10.0 out of 10, Exceptional, (23)
"Beautiful home that suited our girls trip perfectly! The views were absolutely amazing and plenty of areas to hang out and have fun together. Not a large couch/sofa area for watching tv, so if your group needs that it might not be the right fit. Otherwise, it was fantastic!"
The price is $559
$1,259 total
includes taxes & fees
May 28 - May 29
Mansion on De Portola with Vineyard and Mountain view
Aerial view
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views
9.8 out of 10, Exceptional, (91)
"Words can’t express how much we enjoyed staying at Villa de la Vine. The view from the property and some of the rooms was spectacular. The beds were comfortable and we had plenty of towels to accommodate the whole family. Our bride enjoyed the use of the master suite sitting room to prepare for her wedding. The house is stunning and made our few days there relaxing and enjoyable. The house was close to the places we needed to be at and visit. Thank you for sharing beautiful Villa de la Vine with...
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views
View from room
The New Star Motel (1950s Retro Lodging and Retreat Center)
3.5 star property
9.8 out of 10, Exceptional, (15)
"The motel was clean and tidy, nothing fancy, in good condition. The owner was great too! I would definitely stay there again!"
The price is $115
$136 total
includes taxes & fees
May 22 - May 23
The New Star Motel (1950s Retro Lodging and Retreat Center)
Outdoor pool, a heated pool
Fallbrook Tuscan villa oasis!
9.8 out of 10, Exceptional, (96)
"Overall All of us had a great time The place was immaculate!! Great location , really close to town, Mrs. Dirk was fast to answer our call when we had a question, we really enjoyed the stay, for our next getaway and if we have something planned close by We’d love to stay there again Thank you so very much!!"
Fallbrook Tuscan villa oasis!
Property grounds
House with pool/spa/minutes to wineries
9.8 out of 10, Exceptional, (13)
"The home was clean and close to the wineries."
The price is $379
$1,031 total
includes taxes & fees
May 22 - May 23
House with pool/spa/minutes to wineries
Property grounds
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!
9.8 out of 10, Exceptional, (267)
"We were there for a wedding. Perfectly situated just around the corner from Town. Would absolutely stay there again."
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!
Property grounds
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
9.8 out of 10, Exceptional, (25)
"Loved the property we stayed at. Avantstay manages the property and was available for any issues we had 24/7. Only issue was on our end working the app for pool/spa operation, lol."
De Luz by AvantStay | 5 Acre Estate w/ Lake, Pool & Hot Tub
Smart TV, fireplace, books
Fully fenced backyard for pets. Pets stay free!
9.8 out of 10, Exceptional, (46)
"This long weekend getaway was originally for myself, my husband, and our wee little pup. It was our puppy’s first birthday and our wedding anniversary. Sadly, the weekend before we had to send our cat to the other side and so our adult child flew in to say goodbye and grieve with us. We alerted Jay and Darlene of our last minute extra guest which they were kind enough to allow along. This cabin is a dream! I feel we are so lucky to have found it. Plenty of quiet and space for the 3 of us adults...
Fully fenced backyard for pets. Pets stay free!
Outdoor pool, a heated pool
Villa with great view/pool/spa
9.8 out of 10, Exceptional, (9)
"This property is stunning. The house is older but is perfect for large parties. Nothing can describe the view from the backyard. Check in was very easy. It was a self check in process. You don’t get any information about check in until late the night before. I was staying at this house with friends and family as we were planning a wine tasting trip in Temecula. The location of this house was perfect for that and very close to wineries. It’s about a 15-20 minute drive to Old Town Temecula. We...
The price is $529
$1,297 total
includes taxes & fees
May 28 - May 29
Villa with great view/pool/spa
Pool
PRIVATE SINGLE LEVEL HILL TOP ESTATE ON 5 ACRES- 20 MIN TO OLD TOWN TEMECULA
9.8 out of 10, Exceptional, (68)
"We gathered some friends and family who used to go to Coachella together to rent this house, hang out and watch the livestream of the festival in mid-April (since we're too damn old to go anymore, haha). Overall the house was really great and pretty much just as advertised. The big bummer was that the weather ended up being cold, windy, and rainy to the point where we stopped heating the pool on day 1 (to save on propane costs) because there was just no way to enjoy it unfortunately. We did...
PRIVATE SINGLE LEVEL HILL TOP ESTATE ON 5 ACRES- 20 MIN TO OLD TOWN TEMECULA
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See all available properties in Winchester
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.

Winchester Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Winchester private vacation homes
Known landmarks
Menifee Lakes Golf Course, Orange Empire Railroad Museum and Diamond Valley Lake Marina
International airport
San Diego, CA (SAN-San Diego Intl.)

Other types of properties in Winchester you may be interested in

Executive Room | Premium bedding, pillowtop beds, in-room safe, laptop workspace
Pala Mesa Golf Resort
3.5 star property
9.2 out of 10, Wonderful, (122)
"We only stayed there to sleep after a show at Pala Casino and left first thing in the morning. The room was very very clean, bed super comfortable. We checked in late at night, staff was friendly. Check in and check out very fast and efficient. "
The price is $100
$109 total
includes taxes & fees
Jun 5 - Jun 6
Pala Mesa Golf Resort
Casino
Soboba Casino Resort
3.5 star property
9.2 out of 10, Wonderful, (1012)
"The accommodations were excellent. We felt the pride and live if the saboba peopke. Highly recommended. "
The price is $118
$130 total
includes taxes & fees
Jun 11 - Jun 12
Soboba Casino Resort
Front of property - evening/night
Pala Casino Spa And Resort
4.0 star property
8.8 out of 10, Excellent, (1173)
"Nice"
The price is $150
$162 total
includes taxes & fees
Jun 11 - Jun 12
Pala Casino Spa And Resort
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.

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near well known sights in Winchester, or you can choose a secluded option if you're looking for relaxation. Winchester is known for its wineries and coffeehouses. Make sure you have time to check out the bars while you're in the area.

What's the top vacation rental in Winchester?

House with pool/spa/minutes to wineries: This vacation home rental near Winchester is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

Choose from 25 Expedia vacation rentals in Winchester for a memorable vacation.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Western Science Center, or get out into nature at a spot like Diamond Valley Lake Marina. Pechanga Resort & Casino and Soboba Casino are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private properties you can stay in for a short or long stay in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.

Recent reviews of Winchester properties
Expedia verified reviews

Tahquitz Pines Retreat

Tahquitz Pines Retreat

5/5 Excellent
Beautiful Place!
"Our first time at this property. Very clean. Friendly staff. Rachel was very helpful from days before our arrival to our check-in. She made the process flawless and was very professional, warm, and friendly. The pool could use more lounge chairs and towels but I also understand that this property is not 100% open. Everything in our cottage functioned accordingly. Would suggest having several doggy bag dispensers with trash cans around the property. While we came prepared, we noticed some pet owners were not and did not pick up after their pets. We'll definitely be back for longer stays!"
A verified traveler stayed at Tahquitz Pines Retreat
Posted 7 hours ago
Tahquitz Pines Retreat