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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Clear Lake Cottages & Marina
2.5 star property
9.0 out of 10, Wonderful, (271)
"Lovely lakefront cottage with a great kitchenette perfect for making breakfast in! The cottage was clean and well equipped! We wish we could have stayed longer! "
The price is AU$285
includes taxes & fees
16 May - 17 May
Clear Lake Cottages & Marina
Safari West
2.0 star property
9.4 out of 10, Exceptional, (219)
"Incredible experience!"
The price is AU$650
includes taxes & fees
16 May - 17 May
Safari West
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
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1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, July 6-14
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, July 6-14
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
8.8 out of 10, Excellent, (134)
"We were pleased with the home, the view and the grounds. Five adults, 2 kids and 2 dogs were very comfortable. Furniture was nice, there was plenty of dishes, silverware and pots and pans. The owners were super nice and very helpful. We would most definitely stay here again"
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
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
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.0 out of 10, Very good, (10)
"The house is lovey! When we arrived they had not warmed the home it was quite cold inside. The jacuzzi never worked even after we called and Jake came out and assured us he was familiar with the issue! The water remained frigid and the jacuzzi was unusable. Jake was a very nice guy but still no jacuzzi. There were also spider webs in some cabinets and windows."
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
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
includes taxes & fees
19 May - 20 May
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
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
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.
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
Waterfront Cottage w/ Private Pool & Lake View!
9.0 out of 10, Wonderful, (31)
"This is an older but nicely remodeled home. Beautiful views even with a rainy weekend. The lake laps right up to the edge of the property. Very close to town for entertainment but far enough away that you can get alone time. We would make 2 very strong recos. Put up curtains or blinds in the living room; it's disconcerting that the neighbors can see right in. Also, leave an instruction sheet for the TV; it was very challenging trying to figure out how the remote worked and what options were...
Waterfront Cottage w/ Private Pool & Lake View!
Stunning retreat with private hot tub, firepit & 1 acre of country charm
9.2 out of 10, Wonderful, (61)
"The house was generally well appointed. As a tea drinker I always feel slighted when there is no kettle. Some of the pillows are in need of replacement. Loved the bocce and hot tub. Great location! Brochures in tgd house were from 2022 and there were a few cleaning issues, sticky stuff on kitchen floor and used shower cap in the master bath."
Stunning retreat with private hot tub, firepit & 1 acre of country charm
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
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
Home near Sonoma & Calistoga in heart of Wine Country
9.6 out of 10, Exceptional, (21)
"This is an annual event and we love to stay in a house together, cook our meals and spend quality time. This house was perfect for that, especially the amazing outdoor space. And, there was plenty of seating inside as well. Plus, I was able to bring my 9 pound Yorky poo which made the stay complete. Would absolutely stay here again."
Home near Sonoma & Calistoga in heart of Wine Country
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
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
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
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
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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.

Other types of properties in Middletown you may be interested in

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
includes taxes & fees
27 May - 28 May
The Sandman Hotel
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$337
includes taxes & fees
2 June - 3 June
Hyatt Regency Sonoma Wine Country
Flamingo Resort & Spa
4.0 star property
7.8 out of 10, Good, (1000)
"Great stay place! "
The price is AU$268
includes taxes & fees
27 May - 28 May
Flamingo Resort & Spa
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.

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.