Photo by Shannon Willitts

Middletown Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Middletown

Pool
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, (15)
"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
Property grounds
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, (230)
"Beautiful home - extremely clean- the kitchen was well equipped and beautiful! Comfortable beds beds- nice sheets. Very private backyard- nice to sit out and visit and enjoy a bottle of wine. There were 4 of us- two couples. Close walking distance to restaurants and shops. Really enjoyed it. The only thing we would have liked was if there were TV’s in all the bedrooms- not just the Main bedroom. Perfect place to stay in St Helena! ❤️"
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
Interior
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (195)
"This house was perfect to accommodate our family in town for a wedding just up the road at the Culinary Institute. Added perks - walk to downtown and across the street to Beringer which had a lovely spot to enjoy wine and play bocce ball and corn hole. The house was beautiful and spacious. Highly recommend."
The price is AU$3,229
per night
19 May - 20 May
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (208)
"One of our best vacations ever- house was phenomenal!"
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Property grounds
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (156)
"Booked this for my once yearly trip with a friend from 5th grade - we are both 60 this year. Also travelled with my 4 year old shepherd-rottweiler mix. The three of us LOVED the home. So many lovely touches; the owner is very gracious and responsive. The yard is something out of a wine country magazine. Absolutely gorgeous and lots of areas to relax. The beds and pillows are super comfortable (my friend and I are both super picky about comfort). The home temperature was easy to control. We...
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Property grounds
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (78)
"Great property that is close to hiking and wine country. Enjoyed our stay and would recommend."
Cottage home near the Russian River; county parks; numerous wineries
Outdoor dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (199)
"The house was gorgeous, but the views still take the cake. The kitchen is stocked full of everything you could need to cook in, you won't want to leave! William was responsive, and provided plenty of information to guide your stay."
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor pool, a heated pool
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
10.0 out of 10, Exceptional, (113)
"Amazing property and views perfect for 5 couples. We will be back!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
4 bedrooms, WiFi, bed sheets
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
10.0 out of 10, Exceptional, (2)
"My friends and I had a great time! Awesome home and quite comfortable. Difficult to figure out parking with our large group, but otherwise a great experience"
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
Exterior
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"
Chalk Hill Cottage Close to Wineries
Property grounds
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (147)
"Wonderful property, perfect for a get away. All amenities are top notch! Thank you!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Exterior
Modern Luxury - Year-Round Heated Pool - Hot Tub - Fire Pit
10.0 out of 10, Exceptional, (18)
"The house is in Kenwood, which was a perfect location for our group (4 couples), as we spent time in Healdsburg down to the town of Sonoma - so great central location. The house itself has 4 bedrooms , each with its own bathroom. Beautiful yard for outdoor events . Heated pool, etc. House really has it all. Would love to get back sooner than later."
Modern Luxury - Year-Round Heated Pool - Hot Tub - Fire Pit
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (147)
"We went to Healdsburg to visit friends and enjoy the sunny weather. We were delighted with the beautiful vineyard views and comfortable cottage, spacious deck, and many other amenities that the host provided. Being in nature was so relaxing that we spent most of our time at the cottage."
Newly Refurbished! Nest Cottage at ru's Farm.
Outdoor pool, a heated pool
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
10.0 out of 10, Exceptional, (12)
"We fully enjoyed our stay at this home. It had everything we needed to have a nice relaxing time in beautiful Calistoga. Would definitely stay again."
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Fridge, microwave, oven, stovetop
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
10.0 out of 10, Exceptional, (95)
"Lovely and well-stocked property. Host was very communicative and responsive. Only downside was having to leave!!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
A heated pool
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
10.0 out of 10, Exceptional, (20)
"We had a great time. Beautiful property. Picky but why not buy a new iron and ironing board for each house. We had to carry one iron from house to house. You Could spend $100 and be done. I felt like our group went above and beyond to clean and take care of the place while we were there."
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Outdoor dining
Wine Country Harvest Vacation Home
9.8 out of 10, Exceptional, (57)
"This was our second stay at the property. Very comfortable for our group of six. Easy access to wine tastings and great deli nearby for our picnic lunches"
Wine Country Harvest Vacation Home
Exterior
Luxury Napa Valley Estate Surrounded by Vineyards
9.8 out of 10, Exceptional, (24)
"Blown away with this home and property. Couldn’t have imagined how beautiful and spacious it was. The grounds were gorgeous"
Luxury Napa Valley Estate Surrounded by Vineyards
Exterior
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
9.8 out of 10, Exceptional, (78)
"We had a fantastic weekend stay. The house was very clean and comfortable and in an excellent location to walk to the many great places in St. Helena."
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
Outdoor dining
Beautiful 3,000 SF Castle in the Vineyards
9.8 out of 10, Exceptional, (189)
"Wonderful property. It feels like you're in a secluded location since you're surrounded by towering redwoods! This place is centrally located in the valley and was a great location to cycle out from! Michael is a fantastic host and spends as much time with you as needed to make sure you know where to go in the area."
Beautiful 3,000 SF Castle in the Vineyards
Don't see what you're looking for?
See all available properties in Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Middletown Holiday Home Travel Info

Number of holiday homes
3
Popular accommodation
Middletown cabins
Known landmarks
Langtry Estate and Vineyards, Beaver Creek Vineyards and Twin Pine Casino
International airport
Santa Rosa, CA (STS-Sonoma County)

Other types of properties in Middletown you may be interested in

2 outdoor pools, open 7:00 AM to 11:00 PM, free pool cabanas
Harvest Inn
4.5 star property
9.2 out of 10, Wonderful, (1000)
"Awesome place to stay when in Napa"
The price is AU$607
per night
4 June - 5 June
Harvest Inn
Lobby lounge
The Sandman Hotel
3.0 star property
8.2 out of 10, Very good, (1722)
"My spouse and I stayed here for one night. Upon checking in the gentlemen did not seem friendly at all. However, he checked me in quickly. The room was clean and comfortable. The only thing was our sink would not drain and when we called the front desk said they couldn’t send anyone until the following morning when we would check out. I’m glad it was just the sink and not the toilet. The breakfast was basic but good. The pool was nice and the seating area was very nice. It was pet friendly so it...
The price is AU$166
per night
27 May - 28 May
The Sandman Hotel
Breakfast served
Hyatt Regency Sonoma Wine Country
4.0 star property
8.2 out of 10, Very good, (1002)
"and convenient for us. I did have a problem with the HVAC though. Our room was very cold and the temp was 64 F. Oh and I was chilly in bed and I could have used an extra blanket which I would see in some hotels. "
The price is AU$277
per night
2 June - 3 June
Hyatt Regency Sonoma Wine Country
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$285 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its hot springs and wineries. Make sure you have time to check out the spas and casinos during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!: This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

Expedia has 4 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

Robert Louis Stevenson State Park and Boggs Mountain Demonstration State Forest are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Twin Pine Casino and Beaver Creek Vineyards.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.

Recent reviews of Middletown properties
Expedia verified reviews

Hotel E

Hotel E

5/5 Excellent
"Beautiful building, location, easy access to food & drink while in the town, absolutely fabulous staff. And what a great breakfast set up to satisfy us as we headed out of town and into the redwoods."
A verified traveller stayed at Hotel E
Posted 1 day ago
Hotel E