Photo by Matthew Walls

Middletown holiday rentals

We found 58 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Middletown that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as parking and a pool. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Take in the majestic beauty of Middletown

Enjoy the wineries and other features of Middletown. Well known for its hot springs, gardens and spas, this relaxing city won't disappoint. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Middletown

Are you searching for attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middletown a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Chateau Montelena Winery (10.4 mi / 16.8 km)
  • Calistoga Speedway (11.7 mi / 18.9 km)
  • Calistoga Hot Springs (12.2 mi / 19.6 km)
  • Sterling Vineyards (13.2 mi / 21.3 km)
  • Castello di Amorosa (14 mi / 22.5 km)
  • Jordan Vineyard & Winery (14 mi / 22.6 km)

Exploring the natural landscape of Middletown

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Middletown. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Cobb Mountain (7.6 mi / 12.2 km)
  • Old Faithful Geyser of California (10.8 mi / 17.4 km)
  • Petrified Forest (13.7 mi / 22 km)
  • Safari West (14.2 mi / 22.8 km)
  • Kendall-Jackson Wine Estate and Gardens (19.1 mi / 30.7 km)
  • Russian River (19.3 mi / 31.1 km)

Transport to and around Middletown

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 19.6 mi (31.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, California, a popular area to stay is in the vicinity of the town centre. This charming area offers a selection of properties that provide a convenient base for exploring the region. You'll find a delightful mix of quaint shops, local eateries, and easy access to stunning natural landscapes.Additionally, being close to the beautiful Mount Saint Helena allows for fantastic hiking opportunities, where visitors can enjoy breathtaking views of the surrounding vineyards and valleys. The nearby Old Faithful Geyser of California is another top attraction, offering a great experience with its natural geothermal wonders.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of holiday rental, with around 20 properties available throughout the area. These houses typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. For those seeking a cozier atmosphere, several cottages and apartments are also on offer, providing a more intimate setting with essential amenities.
Are there any family house rentals in Middletown?
In Middletown, California, there are several family-friendly house rentals available, suiting those seeking a comfortable stay amidst the beauty of the region. Properties in this area typically feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play safely.Visitors can enjoy the nearby attractions, such as the scenic vineyards and wineries that dot the landscape, superb for family outings. Additionally, the natural surroundings offer opportunities for hiking and exploring the stunning landscapes of the nearby mountains.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, California, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the picturesque Napa Valley region, offers a serene escape surrounded by natural beauty. Many properties in the area come equipped with private pools, hot tubs, and outdoor lounging spaces, superb for relaxation after a day of exploring the local vineyards and scenic landscapes.Travellers can also expect amenities such as fully equipped kitchens, spacious living areas, and often beautiful views of the surrounding hills, making these homes ideal for both families and groups. The proximity to local wineries and natural attractions further enhances the appeal of renting a holiday home in this tranquil destination.
Are there pet-friendly house rentals in Middletown?
In Middletown, there are several pet-friendly house rentals available, offering a comfortable stay for travellers with pets. Many of these properties feature amenities such as spacious yards, allowing pets to roam freely, and outdoor areas where guests can enjoy the beautiful Californian weather. Inside, you can expect well-equipped kitchens, cosy living spaces, and often multiple bedrooms, making them suitable for families or groups.The surrounding area is picturesque, with opportunities for outdoor activities that are pet-friendly. Nearby, you can explore local parks and trails where your furry companions are welcome, providing a great chance to enjoy nature together.
Are there any remote work holiday rentals in Middletown?
In Middletown, California, there are around 28 holiday rentals that cater specifically to remote workers. This charming town, located in the scenic Napa Valley region, offers a tranquil environment that's superb for productivity while enjoying the beauty of nature. Many of these properties come equipped with essential amenities for remote work, including high-speed internet and Wi-Fi, dedicated desks, and comfortable workspaces, ensuring a seamless working experience.Moreover, these rentals often feature spacious living areas and fully equipped kitchens, allowing guests to enjoy home-cooked meals during their stay. The surrounding area boasts beautiful vineyards and stunning landscapes, providing opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Middletown?
In Middletown, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature coffee and tea makers for that essential morning boost. Onsite parking is commonly available, providing convenience for those travelling by car. Additionally, many rentals come with decks or patios, offering outdoor spaces to relax and enjoy the surrounding views. For those needing to catch up on work or plan their adventures, a desk is often included in the accommodations.
When is the best time to visit Middletown for a holiday rental?
The best time to book a holiday rental in Middletown is during the peak season from August to October. October is particularly popular, as visitors can enjoy the beautiful autumn scenery and the mild climate, with temperatures typically ranging from 10 to 20 degrees Celsius. This time of year is superb for outdoor activities such as hiking and wine tasting, especially in the nearby vineyards that showcase the region's stunning fall colours.As the summer crowds begin to dissipate in October, you can experience a more relaxed atmosphere while still enjoying the delightful local attractions. The grape harvest is in full swing, and many wineries host special events and tastings, providing a wonderful opportunity to savour the flavours of the region.For those looking to save a bit on accommodation, December offers a quieter alternative, making it a great time for a peaceful retreat. While the weather is cooler, with temperatures averaging around 5 to 12 degrees Celsius, you can still enjoy the charm of Middletown's natural beauty and cozy up in a lovely rental.
What are the top attractions in Middletown?
In Middletown, California, visitors can enjoy a range of attractions that highlight the area's natural beauty and cultural heritage. The nearby Mount St. Helena offers stunning hiking trails with panoramic views of the surrounding landscape, making it a popular spot for outdoor enthusiasts. The area's geothermal activity can be explored at the Calistoga Hot Springs, which are just a short drive away, providing a relaxing retreat.For those interested in local history, the Middletown Area Historical Museum offers insights into the region's past, featuring exhibits that showcase the heritage of the area. Wine lovers can also venture to the nearby vineyards and wineries in the Calistoga and Napa Valley regions, where tastings and tours provide a delightful experience amidst picturesque scenery.Additionally, the scenic Clear Lake, located a short distance from Middletown, is great for water activities such as fishing, boating, and picnicking along the shores.
Are all fees included in the Middletown holiday homes prices shown on Stayz?
Stayz 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.
Are there any Middletown holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Middletown holiday homes?
You can find great discounts on holiday homes in Middletown on Stayz, 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.
Can I change or cancel my Middletown holiday home booking on Stayz?
To find Middletown holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middletown?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Middletown holiday home?
Book your Middletown holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Middletown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.