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Middletown vacation rentals

We found 337 vacation rentals — enter your dates for availability

Select from 50 houses, 12 condos, and other vacation rentals to find the perfect place for your stay in Middletown. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, like WiFi and parking. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Middletown

Showing deals for:Nov 14 - Nov 21
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Find out more about Middletown

Find out more about Middletown

Why visit Middletown

  1. Outdoor Activities: Enjoy family-friendly beach outings and explore urban parks and private gardens.
  2. Cultural Experiences: Visit the local maritime museum and immerse yourself in the vibrant arts scene.
  3. Charming Neighbourhoods: Discover unique dining and shopping in nearby areas like Point Loma and Little Italy.
  4. Scenic Beaches: Relax on the stunning San Diego shores, just a short drive away from Middletown.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including homes, condos, and apartments.

Popular types of accommodation around Middletown

If you're exploring vacation rentals in Middletown, you're in for a treat! Our platform offers a diverse array of accommodations, including houses, condos, and apartments. Whether you're searching for a spacious apartment in Middletown or looking for monthly rentals, we provide you with transparent information and great savings. Discover the perfect getaway that suits your needs and experience the charm of Middletown!

  • Houses: The top choice for visitors in Middletown, offering spacious and comfortable stays, perfect for families or groups.
  • Condos: A popular option for those seeking a blend of convenience and amenities, ideal for couples or small families.
  • Apartments: A versatile accommodation type, providing a homey atmosphere for solo travellers or extended stays.
  • Cottages: A quaint and charming choice for a peaceful getaway, perfect for a romantic retreat.
  • Villas: Luxurious and spacious, these options offer an upscale experience for those looking to indulge.**

Top attractions around Middletown

Middletown, San Diego, is perfect for outdoor and family beach vacations, offering a variety of attractions. Visitors can explore private gardens, urban parks, and a maritime museum, making it an ideal spot for those seeking cultural experiences and outdoor adventures. Whether you're travelling with family or just looking to enjoy the scenery, Middletown provides a delightful mix of activities to suit every traveller's needs.

  1. Balboa Park: A stunning urban oasis featuring lush gardens, vibrant art installations, and numerous museums. This cultural hub offers a serene escape from the city, perfect for leisurely strolls and artistic exploration.
  2. Hotel Circle: A lively thoroughfare lined with hotels, restaurants, and shopping options, providing a bustling city atmosphere. It's an ideal spot for visitors looking to experience San Diego's vibrant nightlife and dining scene.
  3. Port of San Diego: A modern civic area showcasing waterfront views and bustling activity. This port is a key business hub with opportunities for dining, shopping, and enjoying the picturesque marina.

Things to do recommended for couples

Discover the charm of Middletown, San Diego! Enjoy an enchanting evening at AMSD Concerts, challenge each other at Golf Gardens Miniature Golf, or indulge in romance at Carruth Cellars Winery. Each experience offers a perfect blend of entertainment and adventure for couples looking to connect.

Things to do recommended for families

Your family will love visiting Petco Park, just 4.8km from Middletown, where you can soak in the sports atmosphere. The Balboa Park Carousel, 3.2km away, offers delightful outdoor fun, while De Anza Cove Park, 6.4km distant, provides a serene spot for wellness and relaxation.

Things to do recommended for groups

In Middletown, San Diego, your group can shop at Fashion Valley Mall, enjoy a performance at the San Diego Civic Theatre, and play a round of golf at Riverwalk Golf Club, all within a short distance of 3.2km, offering a blend of family-friendly and entertaining experiences.

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

If you’re planning a trip with a group, family, or pets, or if you’re interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middletown with a group: Think about how many bedrooms you require, along with amenities like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Middletown with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Middletown: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you’re in search of vacation rentals that offer great deals 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 additional features like a parking space, a well-equipped kitchen, or even a private pool during your search.

Where to stay around Middletown

Middletown, San Diego, offers a delightful blend of urban charm and coastal relaxation. Explore the vibrant downtown area, where art and friendly faces abound. Nearby neighborhoods, such as Point Loma and Little Italy, provide unique dining and shopping experiences. For beach lovers, the scenic shores of San Diego are just a short drive away, making it an ideal family vacation destination. Embrace the diverse atmosphere and create lasting memories in this enchanting locale.

  • Downtown San Diego: Located a mere 3.2km from Middletown, Downtown San Diego is the vibrant core of the city, bustling with activity and life. Visitors flock here for a mix of family-friendly attractions and business opportunities. The area boasts a variety of venues including shopping centres, casinos, and theatres, ensuring there is something for everyone. Key landmarks such as the convention centre and stadium are easily accessible, making it a prime spot for events and entertainment.
  • Gaslamp Quarter: Also just 3.2km away, the Gaslamp Quarter is a historic district famed for its Victorian architecture and lively atmosphere. This neighbourhood is a hotspot for families, outdoor enthusiasts, and business travellers alike. Enjoy the eclectic mix of shopping centres, casinos, and theatres. The area is known for its vibrant nightlife and cultural events, with landmarks like the event conference venue and convention centre nearby, making it an ideal destination for both leisure and business activities.
  • Hillcrest: Situated only 1.6km from Middletown, Hillcrest is a charming neighbourhood that offers a unique blend of outdoor spaces and urban living. Known for its inclusivity and vibrant atmosphere, this area is perfect for families and city explorers. Hillcrest features educational venues, shopping centres, and charming shopping malls. The local attractions, including historic sites, urban parks, and private gardens, provide a delightful backdrop for a leisurely day out. Experience the community spirit and diverse culture that make Hillcrest a must-visit.

Best time to go to Middletown

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January57.4°F (14.1°C)Light RainSunnySlightly LowSlightly Low
February56.8°F (13.8°C)Light RainSunnyAverageSlightly Low
March58.1°F (14.5°C)No Rain (Dry)Mostly SunnyAverageAverage
April60.6°F (15.9°C)No Rain (Dry)SunnyAverageAverage
May62.6°F (17.0°C)No Rain (Dry)SunnyAverageAverage
June66.4°F (19.1°C)No Rain (Dry)SunnySlightly HighSlightly High
July70.5°F (21.4°C)No Rain (Dry)SunnySlightly HighSlightly High
August72.3°F (22.4°C)No Rain (Dry)SunnySlightly HighSlightly High
September72.0°F (22.2°C)No Rain (Dry)SunnyAverageAverage
October68.2°F (20.1°C)No Rain (Dry)SunnyAverageSlightly Low
November62.6°F (17.0°C)No Rain (Dry)SunnySlightly LowAverage
December57.4°F (14.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can lead to better prices, as they often fluctuate. Additionally, consider booking a longer stay to unlock substantial savings. To discover a Vrbo property that aligns with your budget, make use of our filters to sort by price, location, and the type of vacation rental you prefer.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your journeys, manage your reservations, and keep track of your travel arrangements. You can easily view your saved or booked properties, which are conveniently organized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Middletown?
In Middletown, vacation houses are the most popular type of rental, with around 41 available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable retreat. Many houses come with outdoor spaces such as gardens or patios, allowing guests to enjoy the pleasant California weather.

Apartments follow as the second most common option, with about 12 rooms found in various neighbourhoods, often providing convenient access to local attractions. These apartments generally feature modern amenities, including kitchen facilities and cosy living spaces.
Are there any beach house rentals in Middletown?
In Middletown, California, there are approximately 97 beach house rentals available, mostly situated near the picturesque Clear Lake and the surrounding natural beauty. These properties typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios where guests can enjoy the stunning views. Many rentals also include extras like private gardens, BBQ facilities, and access to nearby hiking trails, making them ideal for families or groups seeking a tranquil getaway.
How much does it cost to rent a vacation home in Middletown?
Prices for vacation rentals in Middletown 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 Middletown to more spacious homes.
Are there any discounts for Middletown vacation house rentals?
You can find great discounts on house rentals in Middletown 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.
Are there any Middletown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middletown 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.
Can I find long-stay vacation rentals in Middletown?
A long-stay vacation rental in Middletown 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.
When is the best time to visit Middletown for a vacation rental?
July is the most popular time to visit Middletown, California, when the warm summer sun beckons travellers seeking vibrant experiences and outdoor adventures. From May to July, the peak season draws visitors eager to explore the stunning landscapes of wine country, indulge in local cuisine, and partake in outdoor activities like hiking and cycling. The pleasant climate, with temperatures typically reaching the low 30s Celsius, creates ideal conditions for exploring the natural beauty of the area.

During this season, visitors can take part in the lively atmosphere of local events, including farmers' markets and wine tastings, allowing for memorable interactions with the community. The proximity of Middletown to renowned wineries and beautiful parks makes it an excellent base for those looking to combine relaxation with adventure.

For a more budget-conscious option, consider visiting in October. This month offers a unique charm as the summer crowds have thinned, allowing for a more tranquil experience while still enjoying mild temperatures in the low 20s Celsius. October is also a wonderful time to witness the beautiful autumn colours as the landscape transforms, making scenic drives and leisurely strolls particularly enjoyable.
Are there any remote work vacation rentals in Middletown?
In Middletown, California, there is a plentiful selection of remote work-friendly vacation rentals, with around 75 options available. This picturesque area, located in the heart of wine country, provides an ideal setting for those looking to combine work and leisure. Many of the properties feature dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment. High-speed Wi-Fi is commonly available, allowing for seamless connectivity during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Middletown vacation rental?
Book your Middletown 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 Middletown home rental booking on Vrbo?
To find Middletown 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 Middletown 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.

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