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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Outdoor dining
1 Bed Room Casita-Suite with Private Entrance
1 Bed Room Casita-Suite with Private Entrance
9.8 out of 10, Exceptional, (56)
"Worked well as a stopover.Clean, easy access.Excellent communication with manager"
United States
Terry L.
$122 nightly
The price is $132
Nov 4 - Nov 5
Total with taxes and fees
1 Bed Room Casita-Suite with Private Entrance
Fridge, microwave, oven, stovetop
•Charming One-Level Home • Feels Like Home
•Charming One-Level Home • Feels Like Home
•Charming One-Level Home • Feels Like Home
Property grounds
Cozy Mountain View Glamping Tent
Cozy Mountain View Glamping Tent
$155 nightly
The price is $166
Nov 4 - Nov 5
Total with taxes and fees
Cozy Mountain View Glamping Tent
Outdoor dining
Boutique Nature Escape - Stargazer Dome
Boutique Nature Escape - Stargazer Dome
7.4 out of 10, Good, (3)
"What a cool and unique concept - glamping is a far reach as glam has no part in the Stargazer experience, at least for us. I should have known as soon as the signage was out of date driving in to find a path towards Rock Bottom that this would only be the beginning of an eventful night. Be wary of having a vehicle with clearance any smaller of an SUV as my stock Honda Civic was just barely able to handle the dirt roads in this campsite. (a tip not stated once in their many descriptions) to the,...
United States
Anonymous traveler
$196 nightly
The price is $209
Nov 4 - Nov 5
Total with taxes and fees
Boutique Nature Escape - Stargazer Dome
Property grounds
The Pony Experience Farm Stay! 501c3
The Pony Experience Farm Stay! 501c3
8.8 out of 10, Excellent, (6)
"The owner of the property is very nice and wanted us to be as comfortable as possible. Beautiful place with lots of shade. The only complaint would be spider webs. "
United States
Jennifer
$315 nightly
The price is $315
Nov 4 - Nov 5
Total with taxes and fees
The Pony Experience Farm Stay! 501c3
Outdoor pool
Coral Tree House
Coral Tree House
3.0 star property
10.0 out of 10, Exceptional, (21)
"This place is so cute, private, beautiful and also fun! Great hosts. Will come back. "
United States
Amy
$225 nightly
The price is $238
Nov 4 - Nov 5
Total with taxes and fees
Coral Tree House
The Motorist Choice: Queen Bed and Hot Shower, Smoking & Non-smoking Room | 1 bedroom, individually decorated, individually furnished, desk
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3.0 star property
9.8 out of 10, Exceptional, (22)
"Great for the price Unique decor"
United States
Andre
$122 nightly
The price is $137
Nov 5 - Nov 6
Total with taxes and fees
The New Star Motel with Studio-Kitchens: 1950s Extended-Stay Lodging and Retreat Center
3 outdoor pools, pool umbrellas, sun loungers
The Cottages at Golden Village Palms RV Resort
The Cottages at Golden Village Palms RV Resort
3.0 star property
9.4 out of 10, Exceptional, (77)
"Thank you! I will stay here again if I’m in the area again!"
United States
Luisito Ignacio Edenso
$159 nightly
The price is $178
Nov 4 - Nov 5
Total with taxes and fees
The Cottages at Golden Village Palms RV Resort
Exterior
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
10.0 out of 10, Exceptional, (39)
"just a quick one night stay- it was great"
United States
Rick M.
$209 nightly
The price is $231
Nov 4 - Nov 5
Total with taxes and fees
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
Exterior
Beautifully remodeled mountain home with peaceful, private setting
Beautifully remodeled mountain home with peaceful, private setting
8.8 out of 10, Excellent, (72)
"Very clean beaautifful,restful, enjoyed our stay "
United States
Valerie M.
$284 nightly
The price is $310
Nov 4 - Nov 5
Total with taxes and fees
Beautifully remodeled mountain home with peaceful, private setting
Interior
Spacious Studio with Private Entry
Spacious Studio with Private Entry
10.0 out of 10, Exceptional, (59)
"Great stay"
United States
Gege
$135 nightly
The price is $135
Nov 5 - Nov 6
Total with taxes and fees
Spacious Studio with Private Entry
Property grounds
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
10.0 out of 10, Exceptional, (11)
"It was a great place to spend some time with myself."
United States
Irma C.
$190 nightly
The price is $207
Nov 4 - Nov 5
Total with taxes and fees
Wildland Loft: Serene Mountain Retreat w Fireplace, AC, Fire Pit, Hammock, Outdo
Suite | 2 bedrooms, Internet
Dog Friendly A-frame Hot Tub Nature Views
Dog Friendly A-frame Hot Tub Nature Views
2.0 star property
$302 nightly
The price is $332
Dec 2 - Dec 3
Total with taxes and fees
Dog Friendly A-frame Hot Tub Nature Views
Outdoor spa tub
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
8.4 out of 10, Very Good, (131)
"Such a gorgeous and quaint cabin, it was the perfect getaway!! Thank you!"
United States
Lesette
$251 nightly
The price is $273
Nov 4 - Nov 5
Total with taxes and fees
Dog-friendly mountain home with hot tub & amazing views - near town & hiking
Exterior
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
2.0 star property
10.0 out of 10, Exceptional, (1)
"What a wonderful little home away from home! We chose this house for the completely fenced-in yard. We were so pleasantly surprised by the little unexpected amenities like gourmet loose-leaf tea, welcome champagne and a homemade candle to take home. There are beautiful hardwood floors in the living room, kitchen and bathroom; bedrooms both have comfortable carpeting. We stayed for 5 weeks... we have never stayed anywhere for that long and we would definitely stay here again. Margaret is an...
United States
Shanen A.
$331 nightly
The price is $360
Nov 4 - Nov 5
Total with taxes and fees
Central Heat & Air, WiFi, Wall Mural and Fully fenced minutes from downtown
Property grounds
Secluded mystical cabin in Idyllwild-Pine Cove
Secluded mystical cabin in Idyllwild-Pine Cove
8.4 out of 10, Very Good, (7)
"Very nice place to stay while in Idyllwild or vicinity. Close to the town, Nature Center, etc. We stayed for a short weekend trip and accommodation had everything we needed. Thank you Rose!"
United States
Victoria T.
$165 nightly
The price is $165
Dec 1 - Dec 2
Total with taxes and fees
Secluded mystical cabin in Idyllwild-Pine Cove
Fridge, microwave, oven, stovetop
Lakeside Escape, Cozy Getaway
Lakeside Escape, Cozy Getaway
2.0 star property
$142 nightly
The price is $142
Nov 5 - Nov 6
Total with taxes and fees
Lakeside Escape, Cozy Getaway
Property grounds
Cactus Garden Cottage…Best Location!!
Cactus Garden Cottage…Best Location!!
10.0 out of 10, Exceptional, (50)
"Property owner was awesome! Was a perfect cozy stay! I really enjoyed staying here!"
United States
Destiny F.
$169 nightly
The price is $169
Nov 12 - Nov 13
Total with taxes and fees
Cactus Garden Cottage…Best Location!!
Exterior
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
9.6 out of 10, Exceptional, (25)
"It was perfect, we loved the view off the back patio.. Enjoyed the turquoise doors and fridge..Thank you!"
United States
Julie M.
$296 nightly
The price is $322
Dec 3 - Dec 4
Total with taxes and fees
Idyllwild Cabin: HotTub, Fireplace&Mountain Views!
Property grounds
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
10.0 out of 10, Exceptional, (1)
"We were lucky to find this beautiful place when the weather turned and camping was no longer an option. Our host was very accomodating and was able to allow us to check in early to a very clean, spacious private cabin that is more like a light house, with amazing views in the Pine Cove area. Wonderful 5 star stay! "
United States
Susan M.
$257 nightly
The price is $279
Nov 7 - Nov 8
Total with taxes and fees
Quiet cabin in Idyllwild. Stunning Views, Cozy, Private, Pet and kid Friendly.
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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Top Winchester Hotel Reviews

Tahquitz Pines Retreat

Tahquitz Pines Retreat

10/10 Excellent
"Clean room and very friendly staff"
Kylie 1-night trip
Posted 5 hours ago
Tahquitz Pines Retreat

Find out more about Winchester

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 $132 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.

Explore a world of travel with Expedia

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?

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!: Visitors give good reviews to this Winchester vacation home rental, which is located in the mountains and has a fireplace, a patio, 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 stovetop, and a microwave, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

Choose from 34 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 Orange Empire Railroad Museum, or get out into nature at a spot like Diamond Valley Lake Marina. K1 Circuit and Pechanga Resort & 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.