Winchester holiday lettings

We found 207 holiday rentals — enter your dates for availability

Discover a selection of 35 homes and other holiday rentals in Winchester that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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Why visit Winchester

  • Scenic outdoor activities: Enjoy picturesque landscapes through golf courses, lakes, and marinas, perfect for a leisurely day out.
  • Rich historical sites: Visit cultural landmarks like Winchester Cathedral and Winchester Castle to immerse yourself in the area's history.
  • Charming local towns: Explore nearby quaint towns, ideal for relaxed strolls and outdoor pursuits.
  • Family-friendly attractions: Discover a variety of activities suitable for all ages, ensuring fun for everyone.
  • Comfortable accommodations: Choose from a range of holiday rentals, including cosy cottages and private homes for a perfect stay.

Popular types of accommodation in Winchester

Discover the charm of Winchester with our selection of holiday rentals. Whether you’re seeking a private vacation home, a cosy cabin, or a quaint cottage, we have the perfect accommodation in Winchester to suit your needs. Ideal for families, couples, or solo adventurers, our Winchester holiday cottages and rentals provide the comfort and convenience you desire. Explore the historical beauty of this city while enjoying the savings and reassurance of booking with us.

  • Houses: The top choice for visitors to Winchester, offering spacious and comfortable settings perfect for families or groups.
  • Cabins: A favourite for those seeking a rustic escape, these accommodations provide a charming retreat amidst nature.
  • Cottages: These delightful and quaint options are ideal for a cosy getaway, perfect for couples or small families.
  • Apartments: A convenient choice for independent travellers, offering the comforts of home in a compact space.
  • Villas: For a touch of luxury, villas provide spacious living with beautiful surroundings, perfect for a memorable stay.**

Top attractions near Winchester

Winchester, California, offers a charming blend of romantic, outdoor, and family-friendly activities. Visitors can enjoy scenic locations like golf courses, lakes, and marinas. For those interested in culture and history, don't miss the historic sites such as Winchester Cathedral and Winchester Castle. The area promises a delightful city experience with numerous tourist attractions to explore, ensuring a memorable visit for all types of travellers.

  • Diamond Valley Lake Marina: Located 3.1km from Winchester, this marina offers a thrilling outdoor experience with adventure activities, scenic beach areas, and opportunities for water sports amidst a stunning natural backdrop.
  • Lake Perris: Situated 6.8km away, Lake Perris features beautiful beaches and picturesque scenery, making it perfect for romantic strolls, picnics, and outdoor leisure activities, all while enjoying the serene environment.
  • Western Science Center: Just 3.1km from Winchester, this centre provides a fascinating glimpse into archaeology and anthropology, showcasing local culture and history through engaging exhibits and educational programs.

Things to do recommended for couples

For a romantic getaway in Winchester, indulge in wine tasting at Wilson Creek Winery, just 6.8km away, or Ponte Winery, 7.5km away. For a thrilling experience, consider a skydive at Skydive Perris, located 5.6km from Winchester, combining adventure with stunning views.

Things to do recommended for families

Families visiting Winchester can unwind at the serene Lake Perris State Recreation Area, embark on thrilling adventures at Mulligan Family Fun Center, or catch an exhilarating game at the Lake Elsinore Storm stadium, all within a short distance from the charming town.

Things to do recommended for groups

Groups visiting Winchester can enjoy a round at Menifee Lakes Golf Course for a sporty experience, indulge in shopping and entertainment at the Promenade, or seek thrills on the Skull Canyon Zipline for an adventurous day out in the beautiful Californian outdoors.

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

If you're travelling with a group, family, pets, or seeking extended stays, it's essential to apply the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that are pet-friendly. Most of these accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Winchester: If you're in search of holiday rentals offering discounts 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 accommodations. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Winchester

Winchester, California, offers a delightful blend of romantic escapes and family-friendly adventures. Visitors can explore nearby charming towns with lovely atmospheres, perfect for leisurely strolls and outdoor activities. With its budget-friendly options and welcoming locals, Winchester promises an enjoyable getaway. Don't miss the opportunity to experience its beautiful landscapes and local entertainment, making it an ideal destination for a relaxing holiday.

  • Menifee: Located a mere 3.7km from Winchester, Menifee is a vibrant city that offers a charming blend of romantic, outdoor, and family experiences. Known for its picturesque landscapes, visitors can enjoy a variety of activities at local resorts, campgrounds, and recreational areas. Notable attractions include an event conference venue and a lovely lake surrounded by the natural beauty of a national state park, making it an ideal spot for nature lovers and adventure seekers alike.
  • Homeland: Just 1.9km away from Winchester, Homeland is an inviting city that caters to families, outdoor enthusiasts, and couples seeking a romantic getaway. The area boasts several resorts and campgrounds, perfect for enjoying the open air. Highlights include a thrilling theme park, an event conference venue, and a symbolic landmark that enriches the local culture. This community is perfect for those looking to explore and create lasting memories.
  • Dutch Village: Nestled within the area of Winchester, Dutch Village is a quaint spot that beckons visitors with its romantic, outdoor, and entertainment-themed experiences. Travelers can indulge in various activities at local campgrounds, resorts, and even ski facilities during the colder months. Key attractions include a historic college university, an event conference venue, and a local stadium that often hosts events, ensuring a lively atmosphere throughout the year.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 HighAverage
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)SunnyAverageSlightly High
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 cut costs on your upcoming getaway? Being flexible with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new getaways, refine your existing arrangements, or manage your reservations with ease. Your saved or booked properties are neatly categorised into Potential, Upcoming, and Current Trips for your convenience. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/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 travellers with its coffee shops and bars. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Rancho Palomar Winery (12.6 mi / 20.4 km)
  • Callaway Vineyard and Winery (13 mi / 21 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winchester is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Moreno Beach (12.1 mi / 19.5 km)

Travelling to and around Winchester

Fly into Murrieta, CA (RBK-French Valley), the closest airport, located 9.6 mi (15.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly 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 holiday rental?
When considering a holiday rental in Winchester, California, the most appealing area to stay is near the picturesque neighbourhoods that offer both tranquillity and convenience. One of the standout locations is the vicinity around the Hemet-San Jacinto Valley, which provides a charming blend of rural charm and easy access to urban amenities. This area features a diverse selection of properties, suiting various preferences and budgets.

Staying in this region allows you to enjoy the stunning scenery of the surrounding mountains and the lush landscapes that characterize the area. A remarkable attraction nearby is the Diamond Valley Lake, great for outdoor enthusiasts looking to engage in activities such as hiking, fishing, or simply taking in the breathtaking views. Additionally, the Western Science Centre is a fantastic point of interest, showcasing fascinating exhibits related to the region's prehistoric past, making it a great educational stop for families.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester holiday 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 holiday rental accomodation in Winchester?
In Winchester, holiday houses are the most popular type of holiday rental, with approximately 116 available throughout the area. These houses typically feature spacious layouts ideal for families or groups, often including multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Additionally, there are several apartments, mobile homes, cottages, and villas scattered around, providing further options for travellers seeking a variety of experiences.
Are there any family house rentals in Winchester?
In Winchester, California, there are some family-friendly house rentals available, with around 18 options to choose from. This area is a great choice for families looking to enjoy the beautiful surroundings and outdoor activities. Many of these homes offer spacious living areas great for gatherings, along with fully equipped kitchens where families can prepare meals together. Outdoor amenities like private backyards or patios provide a nice space for children to play and for families to relax.

The locale is conveniently located near various attractions, including local parks and recreational areas, ideal for family outings. Visitors can explore nearby hiking trails and enjoy the natural beauty of the region.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, California, there are several holiday homes available for rent that feature pools and hot tubs, with around 15 options to choose from. This area is known for its pleasant climate and scenic surroundings, making it an attractive destination for travellers seeking relaxation and outdoor activities. Many of these properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas ideal for family gatherings or entertaining.

Additionally, the homes typically include amenities such as fully equipped kitchens, barbecue facilities, and comfortable living spaces. The surrounding region offers opportunities for hiking and enjoying the natural beauty of Southern California, further enhancing the appeal of a holiday rental in Winchester.
Can I find long-stay holiday rentals in Winchester?
A long-stay holiday 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 several pet-friendly house rentals available, offering a range of amenities that cater to both humans and their furry companions. Many of these holiday homes come equipped with spacious backyards, often featuring secure fencing and outdoor seating areas, allowing pets to enjoy the fresh air safely. Inside, travellers can expect fully equipped kitchens, comfortable living spaces, and multiple bedrooms, making them ideal for families or groups.

The surrounding area also provides ample opportunities for pet-friendly activities. Nearby, the expansive Santa Rosa Plateau Ecological Reserve offers scenic trails great for hiking with pets, allowing for exploration of the beautiful Californian landscape. Additionally, local parks in Winchester are welcoming to dogs, providing open spaces for play and socialising.
Are there any remote work holiday rentals in Winchester?
In Winchester, California, there are numerous holiday rentals ideal for remote work, with around 112 options available. Many of these properties cater specifically to the needs of remote workers, offering amenities such as dedicated desk spaces and complimentary Wi-Fi, ensuring a productive environment.

Travellers can expect comfortable accommodations featuring well-equipped living areas, allowing for both work and relaxation. The area itself is surrounded by beautiful landscapes, providing a peaceful backdrop for those balancing work and leisure. Additionally, Winchester's proximity to local amenities means that shops and restaurants are just a short drive away, making it convenient for remote workers to enjoy their time off after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities cater to a comfortable and convenient stay. Most holiday rentals feature fully equipped kitchens, allowing guests to prepare their own meals. Onsite parking is commonly available, which is a significant advantage for those travelling by car. Many properties also include a coffee and tea maker, great for enjoying a warm beverage at any time. Additionally, outdoor spaces such as decks or patios are typical, providing a lovely area to relax and enjoy the pleasant Californian weather.
When is the best time to visit Winchester for a holiday rental?
The peak season for holiday rentals in Winchester typically falls between April and June, with May standing out as the most popular month to visit. This vibrant time of year attracts travellers eager to explore the area's picturesque vineyards and enjoy the beautiful blooming landscapes of Southern California.

During May, visitors can expect pleasantly warm temperatures, generally ranging from 15 to 30 degrees Celsius, creating ideal conditions for outdoor activities. Whether you're wandering through the local wineries or taking leisurely hikes in the surrounding hills, you'll find a wealth of experiences that cater to adventure and relaxation alike.

For those looking for a more budget-friendly option, November is a wonderful time to consider a visit. With fewer tourists around, you can enjoy a quieter atmosphere while still appreciating the area's natural beauty. The stunning autumn colours and cooler temperatures can make for a charming getaway, great for scenic drives and exploration at a leisurely pace.
How early should I book a Winchester holiday rental?
Book your Winchester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester?
In Winchester, California, visitors can enjoy a variety of attractions that highlight the area's natural beauty and community spirit. The nearby Lake Skinner Recreation Area offers opportunities for fishing, picnicking, and hiking, making it a great spot for outdoor enthusiasts. The area also features scenic trails that are great for walking or cycling, providing a chance to take in the picturesque surroundings.

The Temecula Valley Wine Country is just a short drive away, where travellers can explore numerous wineries and enjoy tastings amid beautiful vineyard landscapes. The charming Old Town Temecula, with its historic buildings and vibrant shops, adds a unique cultural experience to the visit.

For those interested in history, the nearby city of Murrieta has several parks and recreational facilities, while the Santa Rosa Plateau Ecological Reserve offers educational opportunities about the local ecosystem.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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