Middletown holiday lettings
We found 446 holiday rentals — enter your dates for availability
Discover a selection of 28 homes and other holiday rentals in Middletown that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts – Middletown
Showing deals for:20 Nov - 27 Nov

Excellent
(8 reviews)
1920 Victorian Home 8 BDR 3BA Heart of little Italy Large Families or Business
San Diego
£10,210
for 7 nights, 1 home
£1,459 per night
includes taxes & fees

Exceptional
(6 reviews)
Modern Farmhouse in the Heart of San Diego
San Diego
£5,014
for 7 nights, 1 home
£716 per night
includes taxes & fees

Wonderful
(69 reviews)
Bright and Quirky Hillcrest Craftsman
San Diego
£1,084
for 7 nights, 1 home
£155 per night
includes taxes & fees

Exceptional
(105 reviews)
Buddha's Zen Retreat-a Lush Tropical Estate - Near Zoo, Beaches, Downtown, Parks
San Diego
£1,632
for 7 nights, 1 home
£233 per night
includes taxes & fees

Exceptional
(45 reviews)
Gated Canyon Home Near Zoo & Beaches
San Diego
£1,843
for 7 nights, 1 home
£263 per night
includes taxes & fees

Exceptional
(24 reviews)
Stunning Little Italy Villa - Private Hot Tub - Minutes to the Convention Center
San Diego
£1,601
for 7 nights, 1 apartment
£229 per night
includes taxes & fees

Wonderful
(52 reviews)
Adorable Quirky Hideaway BIG Private Enclosed Yard
San Diego
£841
for 7 nights, 1 home
£120 per night
includes taxes & fees

Wonderful
(9 reviews)
Remodeled 1bd Craftsman Bungalow
San Diego
£1,941
for 7 nights, 1 home
£277 per night
includes taxes & fees

Exceptional
(11 reviews)
Trendy Mission Hills Condo, Parking, Central
San Diego
£1,325
for 7 nights, 1 apartment
£189 per night
includes taxes & fees

Exceptional
(43 reviews)
4 BD Entire House Located Close to Downtown and Little Italy!
San Diego
£2,706
for 7 nights, 1 home
£387 per night
includes taxes & fees

Exceptional
(73 reviews)
*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE
San Diego
£2,083
for 7 nights, 1 home
£298 per night
includes taxes & fees

Exceptional
(44 reviews)
Paradise in Old Town - close to Seaworld / MCRD
San Diego
£1,085
for 7 nights, 1 apartment
£155 per night
includes taxes & fees

Wonderful
(8 reviews)
Sunset in Old Town with a Perfect Location
San Diego
£1,176
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Middletown

City24 Hotel Little Italy Mission Hills
Sleeps 2 · 1 bedroom

The Gem of Mission Hills: Luxury 5BR Home with Luxe Amenities and views`
Sleeps 12 · 5 bedrooms · 3+ bathrooms

New Modern Condo in The Hills! Sleeps 2-4 - Only 5 min to Little Italy
Sleeps 4 · 1 bedroom · 1 bathroom

Mission Hills-Entire Guest House-Center of it all
Sleeps 3 · 1 bedroom · 1 bathroom

Beautiful Canyon Cottage on a huge private lot
Sleeps 6 · 3 bedrooms · 1 bathroom

Custom home with cabana, heated pool, spa and view
Sleeps 5 · 3 bedrooms · 3 bathrooms
Top rated rentals - Middletown

A hidden gem!
What a lovely place! We’d totally recommend it. The Villa is gorgeous, the outside space is beautiful, the location perfect and the owners friendly, helpful and very very thoughtful. You can see evidence of this through the Villa with a well supplied kitchen, bathroom and utility; beautiful bedrooms (the fairy lights in the master were so pretty). We would definitely stay again and recommend this place to anyone (although please note if you have mobility issues you can only access it via steps).
Karen T.
Stayed Jul 2024

Finish of tour across US
Always wanted to see San Diego and this apartment made it a great experience. It is a steady 20 min walk into little Italy where there are great restaurants. USS midway and the zoo plus Balboa park are great places to visit. Tiffany and Bill are fantastic hosts and the apartment is perfect as a home from home . View of the airport is really interesting and not at all an eyesore to the view in our opinion. Great visit!!!!!
DAVID D.
Stayed Jun 2024

Perfect
A few things not working and wrong door code given but otherwise perfect. Communication is not with owner so a little disjointed. Lovely place (very close to airport) great location, everything you;d need
Nick A.
Stayed Feb 2024

Great San Diego apartment
We stayed here last week for five days while visiting San Diego. Apartment is just like the photos and the views are amazing though you do get ever so slightly obsessed with the planes landing and taking off...
The beds are huge and the linens lovely. Great bathrooms. The kitchen is good and the sitting room comfy. The planes are noisy when outside but the double glazing keeps the noise minimal when inside.
It is very hilly to walk anywhere but not impossible and Uber’s plentiful.
Overall a great apartment
Debbie C.
Stayed Aug 2018
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a holiday home in Middletown?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middletown holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Middletown?
A long-stay holiday 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 holiday rental?
July is the most popular month to visit Middletown, California, as it falls within the peak season that spans from May to July. This vibrant period attracts travellers eager to enjoy the warm sunshine and outdoor activities, making it ideal for hiking, vineyard tours, and relaxation in the beautiful surroundings of Napa Valley.During these summer months, you can expect pleasant temperatures averaging around 30°C, superb for exploring the local wineries and indulging in al fresco dining experiences. The atmosphere is lively, with plenty of events and festivals that showcase the region's rich culture and community spirit.For those looking for a more budget-friendly option, consider visiting in October. This month offers a tranquil experience, allowing for peaceful exploration of the stunning fall landscapes. With fewer tourists around, you can savour the beauty of the changing leaves and take advantage of off-peak pricing for holiday rentals.
How early should I book a Middletown holiday rental?
Book your Middletown 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 Middletown, California, United States of America?
In Middletown, California, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. One of the key points of interest is the stunning Mount St. Helena, which offers hiking trails with breathtaking views of the surrounding landscape. Nearby, the historic Middletown Depot, which dates back to the late 19th century, provides a glimpse into the town's history and charm.For those interested in wellness and relaxation, the Harbin Hot Springs is a popular destination, known for its natural hot springs and tranquil setting, superb for a rejuvenating retreat. Additionally, the area is surrounded by vineyards and wineries, making it an excellent spot for wine enthusiasts looking to explore local tastings and tours.The nearby Robert Louis Stevenson State Park features hiking trails and picnic areas, ideal for outdoor activities amidst the stunning scenery.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown 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 Middletown 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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