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

Room
Dining
Interior
Living area
Excellent
(8 reviews)

1920 Victorian Home 8 BDR 3BA Heart of little Italy Large Families or Business

San Diego

8% off
£10,210
for 7 nights, 1 home
£1,459 per night
includes taxes & fees
1920 Victorian Home 8 BDR 3BA Heart of little Italy Large Families or Business
Interior
Private kitchen
Interior
Dining
Exceptional
(6 reviews)

Modern Farmhouse in the Heart of San Diego

San Diego

8% off
£5,014
for 7 nights, 1 home
£716 per night
includes taxes & fees
Modern Farmhouse in the Heart of San Diego
Dining
Living area
Room
Interior
Wonderful
(69 reviews)

Bright and Quirky Hillcrest Craftsman

San Diego

10% off
£1,084
for 7 nights, 1 home
£155 per night
includes taxes & fees
Bright and Quirky Hillcrest Craftsman
Room
Property grounds
Interior
Deck with hot tub
Exceptional
(105 reviews)

Buddha's Zen Retreat-a Lush Tropical Estate - Near Zoo, Beaches, Downtown, Parks

San Diego

15% off
£1,632
for 7 nights, 1 home
£233 per night
includes taxes & fees
Buddha's Zen Retreat-a Lush Tropical Estate - Near Zoo, Beaches, Downtown, Parks
Seating area with Desk.  Wifi access 2 g and 5 g.
Enjoy the deck and relax in nature.
King size sleeper with foam mattress and high quality linens.
Individually controlled climate in the living spaces.
Exceptional
(45 reviews)

Gated Canyon Home Near Zoo & Beaches

San Diego

7% off
£1,843
for 7 nights, 1 home
£263 per night
includes taxes & fees
Gated Canyon Home Near Zoo & Beaches
Interior
Interior
Room
Dining
Exceptional
(24 reviews)

Stunning Little Italy Villa - Private Hot Tub - Minutes to the Convention Center

San Diego

7% off
£1,601
for 7 nights, 1 apartment
£229 per night
includes taxes & fees
Stunning Little Italy Villa - Private Hot Tub - Minutes to the Convention Center
Private kitchen
Living area
Room
Exterior
Wonderful
(52 reviews)

Adorable Quirky Hideaway BIG Private Enclosed Yard

San Diego

10% off
£841
for 7 nights, 1 home
£120 per night
includes taxes & fees
Adorable Quirky Hideaway BIG Private Enclosed Yard
Living area
Room
Private kitchen
Dining
Wonderful
(9 reviews)

Remodeled 1bd Craftsman Bungalow

San Diego

8% off
£1,941
for 7 nights, 1 home
£277 per night
includes taxes & fees
Remodeled 1bd Craftsman Bungalow
Exterior
Private kitchen
Interior
Interior
Exceptional
(11 reviews)

Trendy Mission Hills Condo, Parking, Central

San Diego

11% off
£1,325
for 7 nights, 1 apartment
£189 per night
includes taxes & fees
Trendy Mission Hills Condo, Parking, Central
Room
Living area
Private kitchen
Living area
Exceptional
(43 reviews)

4 BD Entire House Located Close to Downtown and Little Italy!

San Diego

7% off
£2,706
for 7 nights, 1 home
£387 per night
includes taxes & fees
4 BD Entire House Located Close to Downtown and Little Italy!
Living area
Private kitchen
Living room
Outdoor dining
Exceptional
(73 reviews)

*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE

San Diego

8% off
£2,083
for 7 nights, 1 home
£298 per night
includes taxes & fees
*Charming* Family & Couples Friendly 4 BR ENTIRE HOUSE
Property grounds
Interior
Living area
Private kitchen
Exceptional
(44 reviews)

Paradise in Old Town - close to Seaworld / MCRD

San Diego

10% off
£1,085
for 7 nights, 1 apartment
£155 per night
includes taxes & fees
Paradise in Old Town - close to Seaworld / MCRD
Living area
Interior
Exterior
Living area
Wonderful
(8 reviews)

Sunset in Old Town with a Perfect Location

San Diego

10% off
£1,176
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
Sunset in Old Town with a Perfect Location
  • 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, pools, gardens and more
  • More for less

    More 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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