Photo by Betsy Wood

Winchester vacation rentals

We found 184 vacation rentals — enter your dates for availability

Discover a selection of 31 homes and other vacation rentals in Winchester that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the amenities you need and want, including WiFi and parking. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Winchester

Showing deals for:Nov 14 - Nov 21

Image gallery for Pool fun in Murrieta, 35ft water slide, large jacuzzi, dog friendly.

Waterfalls and water slide fun for all
10 out of 10 rating
Exceptional
(19 reviews)

Pool fun in Murrieta, 35ft water slide, large jacuzzi, dog friendly.

Murrieta, CA

22% off
Price is CA $809
CA $7,406 total
includes taxes & fees
Pool fun in Murrieta, 35ft water slide, large jacuzzi, dog friendly.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winchester

Find out more about Winchester

Why visit Winchester

  1. Outdoor Adventures: Winchester offers stunning landscapes for hiking, golfing, and water activities at scenic lakes and marinas.
  2. Romantic Getaways: Enjoy a charming atmosphere perfect for couples seeking a peaceful escape.
  3. Family-Friendly Experiences: Engage in fun-filled activities suitable for visitors of all ages.
  4. Diverse Accommodations: Choose from cozy cottages, spacious homes, and luxurious villas to suit your vacation needs.
  5. Welcoming Neighborhoods: Explore friendly communities that embody the rich history and culture of the area.

Popular types of accommodation in Winchester

Discover a variety of vacation rentals in Winchester, from charming holiday cottages to spacious houses, inviting cabins, and luxurious villas. Whether you're planning a family getaway or a romantic escape, there's an array of Winchester cottage rentals to suit your needs. With transparency, savings, and reassurance at the forefront, finding the perfect accommodation for your Canadian adventure has never been easier!

  • Houses: The top choice for visitors to Winchester, these homes offer spacious and comfortable living for families or groups.
  • Cabins: A popular option for those seeking a rustic experience, cabins are perfect for enjoying the natural beauty of the area.
  • Villas: These luxurious accommodations provide a blend of style and comfort, ideal for a relaxing getaway.
  • Apartments: A convenient choice for solo travellers or couples, apartments offer modern amenities in a compact space.
  • Cottages: Charming and quaint, cottages provide a cozy atmosphere for a peaceful retreat.**

Top attractions in Winchester

Winchester, California, is perfect for romantic getaways, outdoor adventures, and family vacations. Visitors can explore a variety of attractions, including golf courses, scenic lakes, and marinas. The area offers a rich blend of cultural experiences and outdoor activities, making it an ideal destination for those seeking a beach experience and the beauty of nature. Enjoy all that this charming locale has to offer during your visit!

  1. Diamond Valley Lake Marina: Nestled 8.0km from Winchester, this marina offers a vibrant outdoor experience with opportunities for boating, fishing, and beach activities. Enjoy the adventure vibes as you explore the scenic lake surroundings.
  2. Lake Perris: Located 17.7km away, Lake Perris is perfect for a romantic getaway. Its picturesque scenery, sandy beaches, and outdoor activities make it an ideal spot for relaxation and adventure.
  3. Western Science Center: Situated 8.0km from Winchester, this centre showcases impressive archaeological and anthropological exhibits, immersing visitors in the region's rich cultural heritage.

Things to do recommended for couples

Winchester offers a perfect romantic getaway for couples. Enjoy a delightful wine tasting at Wilson Creek Winery or Ponte Winery, both exuding charming vibes. For the adventurous duo, Skydive Perris promises an exhilarating experience just a short drive away. Embrace love and adventure in this beautiful locale!

Things to do recommended for families

In Winchester, families can unwind at Lake Perris State Recreation Area, enjoy thrilling sports at Lake Elsinore Storm, The Diamond, and have a blast at Mulligan Family Fun Center. These experiences promise adventure and relaxation for everyone!

Things to do recommended for groups

Groups visiting Winchester can enjoy a round of golf at Menifee Lakes Golf Course, try their luck at Soboba Casino, or indulge in shopping and entertainment at the Promenade. Each venue offers a unique atmosphere perfect for making lasting memories together.

What do I need to keep in mind when booking a vacation in Winchester

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group get-togethers. Thankfully, you can easily filter for all of these options—and much more—on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to keep in mind the distance to family-friendly attractions.
  • Taking your pets with you to Winchester: For many families, a vacation isn’t truly enjoyable without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that every member of the family, including your four-legged friend, feels completely at home.
  • Planning for a long term stay visiting Winchester: If you're seeking vacation rentals with great offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay in Winchester

Winchester, California, offers a delightful blend of romantic getaways and family-friendly experiences. Nestled in a picturesque setting, this charming city is perfect for outdoor adventures and relaxing excursions. Explore the welcoming neighborhoods, indulge in local accommodations, and take advantage of the excellent location to discover nearby attractions. Whether you’re seeking a romantic escape or a fun-filled family vacation, Winchester promises an unforgettable experience surrounded by friendly people and rich history.

  • Menifee: Located a mere 9.7km from Winchester, Menifee is a vibrant city known for its romantic ambiance and outdoor activities. Visitors are drawn to its variety of attractions, including a bustling casino and a serene resort for a perfect getaway. Families will appreciate the campgrounds and the nearby state park, ideal for hiking and picnicking. A highlight of Menifee is its beautiful lake, which offers opportunities for fishing and boating, making it a delightful spot for nature lovers and anyone looking to unwind in a picturesque setting.
  • Homeland: Just 4.8km from Winchester, Homeland is a quaint city that caters to families and outdoor enthusiasts alike. This charming locale features a casino and a selection of campgrounds for those looking to immerse themselves in nature. Visitors can enjoy a day at the nearby theme park, filled with rides and attractions for all ages. Homeland also boasts event conference venues and symbolic landmarks that reflect its rich culture, making it an excellent destination for both recreation and relaxation.
  • Dutch Village: Nestled within the area of Winchester, Dutch Village is a quaint village perfect for romantic outings and entertainment. This locale features a variety of activities, including access to a casino and charming resorts. The local campground is ideal for family-friendly adventures. Visitors can enjoy events at the conference venues or catch a game at the nearby stadium, while the symbolic landmarks provide a glimpse into the village's history and culture, ensuring a fulfilling experience for all.

Best time to go to Winchester

If you're planning a trip to Winchester, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from April to June, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January51.4°F (10.8°C)Light RainSunnyAverageSlightly Low
February51.6°F (10.9°C)Light RainSunnyAverageSlightly Low
March54.7°F (12.6°C)Light RainMostly SunnyAverageSlightly Low
April59.5°F (15.3°C)No Rain (Dry)SunnySlightly HighAverage
May63.1°F (17.3°C)No Rain (Dry)SunnySlightly HighSlightly High
June70.5°F (21.4°C)No Rain (Dry)SunnySlightly HighSlightly High
July76.6°F (24.8°C)No Rain (Dry)SunnyAverageSlightly High
August77.5°F (25.3°C)No Rain (Dry)SunnyAverageAverage
September74.5°F (23.6°C)No Rain (Dry)SunnyAverageAverage
October66.0°F (18.9°C)No Rain (Dry)SunnySlightly LowAverage
November57.4°F (14.1°C)No Rain (Dry)SunnySlightly LowAverage
December50.2°F (10.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. You might also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you previously paused, or manage your existing travel arrangements. You’ll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the charming city of Winchester

Enjoy the wineries and other features of Winchester. This romantic and relaxing city entices travelers with its coffeehouses and bars. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Winchester

Do you want to discover attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Winchester a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Menifee Lakes Golf Course (4.6 mi / 7.4 km)
  • Soboba Springs Country Club (10.8 mi / 17.4 km)
  • Wilson Creek Winery (11.5 mi / 18.4 km)
  • Ponte Winery (12.1 mi / 19.4 km)
  • Peltzer Winery (12.3 mi / 19.8 km)
  • Avensole Winery (12.5 mi / 20.1 km)

Exploring the natural landscape of Winchester

Whether you're an adventurous traveler or just want to take in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Diamond Valley Lake Marina (4.6 mi / 7.4 km)
  • Lake Perris (11.4 mi / 18.3 km)
  • Lake Perris State Recreation Area (11.7 mi / 18.8 km)
  • Lake Elsinore (15.7 mi / 25.2 km)
  • Grand Tradition Estate and Gardens (25.6 mi / 41.2 km)
  • Perris Beach (12.2 mi / 19.6 km)

Traveling to and around Winchester

Fly into Murrieta, CA (RBK-French Valley), the closest airport, located 9.6 mi (15.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into San Bernardino, CA (SBD-San Bernardino Intl.), which is 28.6 mi (46 km) away.

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When considering a vacation rental in Winchester, California, a popular area to stay in is the vicinity of the French Valley. This charming neighbourhood offers a peaceful atmosphere while being conveniently close to several attractions. The French Valley Community Park is a local favourite for families, featuring sports fields, walking trails, and picnic areas, making it a great spot for relaxation and outdoor activities. Additionally, the nearby Diamond Valley Lake is a stunning natural reserve that invites visitors for hiking, fishing, and boating, providing a lovely backdrop for a day out in nature.

Another appealing area is the Winchester Hills neighbourhood, which boasts beautiful views and a tranquil vibe. This area is ideal for those looking to unwind while still being within reach of local conveniences. Moreover, it is a short drive away from the lively town of Murrieta, where you can find a variety of shops and dining options.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation rentals in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes.
Are there any discounts for Winchester vacation house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, vacation houses are the most popular type of accommodation, with about 28 available throughout the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many houses also include outdoor spaces, such as gardens or patios, superb for enjoying the pleasant California weather. Additionally, there are several mobile homes and villas available, offering a unique alternative for travellers looking for something different. Apartments are also present but in fewer numbers, providing a more compact option for those wanting a simpler stay.
Are there any family house rentals in Winchester?
In Winchester, California, there are numerous family-friendly house rentals available—specifically around 20 options. This area is known for its pleasant suburban vibe and proximity to attractions like the Santa Rosa Plateau Ecological Reserve, which offers scenic trails superb for family outings.

Many of these homes provide spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play. Visitors can also find amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.
Can I rent a vacation home with a pool or hot tub in Winchester?
In Winchester, California, there are several vacation homes available for rent that feature pools and hot tubs, with around 15 options to choose from. This charming area, located in Riverside County, offers a variety of properties that cater to different preferences and group sizes. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas ideal for relaxation and social gatherings.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winchester?
In Winchester, there are numerous pet-friendly house rentals available, offering a variety of amenities that cater to both travellers and their furry companions. Many of these properties feature spacious backyards, which are great for pets to roam, as well as modern kitchens and comfortable living areas for relaxation.

The neighbourhoods around Winchester are known for their family-friendly atmosphere, and you can often find homes equipped with conveniences such as Wi-Fi, air conditioning, and laundry facilities. Some rentals may also include additional features like outdoor seating areas, fire pits, or even pools, making them ideal for enjoying the sunny California climate.
Are there any remote work vacation rentals in Winchester?
In Winchester, California, there are numerous options for remote work vacation rentals, with around 27 properties available. Travellers can expect accommodations that cater specifically to remote work needs, featuring amenities such as high-speed Wi-Fi, dedicated office spaces with desks and comfortable chairs, and additional equipment like computer monitors and safes for added security. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winchester?
In Winchester, popular vacation rental amenities typically include kitchens equipped with essential appliances such as refrigerators and cookware, allowing guests to prepare their own meals. Many properties also feature pools, providing a refreshing option for relaxation and leisure. Additionally, travellers can expect coffee makers in their accommodations, superb for enjoying a morning brew.
When is the best time to visit Winchester for a vacation rental?
May is widely regarded as the best time to visit Winchester for a vacation rental, as it falls within the peak season that runs from April to June. During this period, the weather is typically warm and inviting, providing an ideal backdrop for outdoor activities such as hiking in the nearby Santa Rosa Plateau or enjoying leisurely strolls through the picturesque vineyards that characterize the region.

Spring in Winchester offers comfortable temperatures, often reaching the low 20s Celsius, creating a superb environment for sightseeing and exploring local attractions. Visitors can immerse themselves in the vibrant local culture by attending farmers' markets and outdoor events that spring to life during this time.

If you're looking for a more economical option, consider visiting in November. Although it's outside the peak tourist season, this month offers a unique charm with cooler temperatures, typically around 15 degrees Celsius, and fewer crowds. It's a fantastic opportunity to enjoy the tranquillity of the area while experiencing its natural beauty, particularly as the fall foliage adds a lovely touch to the landscape.
How early should I book a Winchester vacation rental?
Book your Winchester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winchester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Rentals ideas

Hemet Vacation Rentals
Standard Link for Hemet
La Quinta Vacation Rentals
Standard Link for La Quinta
Sea Ranch Vacation Rentals
Standard Link for Sea Ranch
San Diego Vacation Rentals
Standard Link for San Diego
Palm Springs Vacation Rentals
Standard Link for Palm Springs
Huntington Beach Vacation Rentals
Standard Link for Huntington Beach
Indio Vacation Rentals
Standard Link for Indio
Monterey Vacation Rentals
Standard Link for Monterey
Rancho Mirage Vacation Rentals
Standard Link for Rancho Mirage
Newport Beach Vacation Rentals
Standard Link for Newport Beach
La Jolla Vacation Rentals
Standard Link for La Jolla
San Clemente Vacation Rentals
Standard Link for San Clemente
San Jose Vacation Rentals
Standard Link for San Jose
Carlsbad Vacation Rentals
Standard Link for Carlsbad
Santa Cruz Vacation Rentals
Standard Link for Santa Cruz
Indian Wells Vacation Rentals
Standard Link for Indian Wells
Sonoma Vacation Rentals
Standard Link for Sonoma
Carmel Vacation Rentals
Standard Link for Carmel
Anaheim Vacation Rentals
Standard Link for Anaheim
Oceanside Vacation Rentals
Standard Link for Oceanside
Palm Desert Vacation Rentals
Standard Link for Palm Desert
Cathedral City Vacation Rentals
Standard Link for Cathedral City
Big Bear Lake Vacation Rentals
Standard Link for Big Bear Lake
Santa Barbara Vacation Rentals
Standard Link for Santa Barbara
Napa Vacation Rentals
Standard Link for Napa
Laguna Beach Vacation Rentals
Standard Link for Laguna Beach

People also search for

Newport Beach Resorts
Standard Link for Newport Beach
Palm Desert Apartments
Standard Link for Palm Desert
Vacation rentals with pool in Palm Springs
Standard Link for Palm Springs
Palm Springs Apartments
Standard Link for Palm Springs