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Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Safari West
2.0 star property
9.4 out of 10, Exceptional, 220 reviews
"Great experience with a great staff "
The price is €504
includes taxes & fees
19 Jun - 20 Jun
Safari West
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, 200 reviews
"This is the perfect house to stay in with a large group! The hosts are great and very responsive. The house is beautiful and has plenty of bedrooms and bathrooms for everyone! The location could not be better and is right off the main road. Overall an amazing experience and would recommend to everyone!"
The price is €2,021
includes taxes & fees
19 Jun - 20 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, 15 reviews
"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
Clear Lake Cottages & Marina
2.5 star property
9.0 out of 10, Wonderful, 272 reviews
"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 €166
includes taxes & fees
19 Jun - 20 Jun
Clear Lake Cottages & Marina
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, 82 reviews
"Stayed mid week for several days. Overall a very nice experience. Super clean and quiet!"
Cottage home near the Russian River; county parks; numerous wineries
Stunning retreat with private hot tub, firepit & 1 acre of country charm
9.2 out of 10, Wonderful, 65 reviews
"Wonderful house and location. It was very private but easy access to wineries and restaurants. We did have a few small issues with things like the door entry system not functioning properly and the firepit gas running out, but overall it was a very nice rental!"
Stunning retreat with private hot tub, firepit & 1 acre of country charm
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
10.0 out of 10, Exceptional, 114 reviews
"Beautiful house to share with my husband and 5 of our friends. The house has everything you hope for and the host was excellent! Would def stay again and again!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, 161 reviews
"This a perfect house to stay in for visiting Sonoma and Napa. It’s a quiet, clean very thoughtfully furnished house. Kitchen was very user friendly and fully stocked. Nice outdoor space with table to have meals, seating area. We will definitely consider this house to come back again. The host is welcoming and accommodating. Thank you!!!"
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.6 out of 10, Excellent, 13 reviews
"This property was perfect for our writing retreat! It was spacious and comfortable, and set in a beautiful location. Would absolutely stay again!"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
A Stylish Getaway In The Heart Of Sonoma Wine Country
10.0 out of 10, Exceptional, 144 reviews
"We enjoyed our very comfortable stay in Kenwood. Great location – easy walk to some solid restaurants. Nice, clean place set in a lovely environment. Host was very pleasant and communicated promptly. The kitchen is well set-up for eating in."
A Stylish Getaway In The Heart Of Sonoma Wine Country
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, 231 reviews
"The house is beautiful. We all enjoyed it and the location is perfect."
The price is €1,367
includes taxes & fees
13 Jul - 14 Jul
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
10.0 out of 10, Exceptional, 3 reviews
"House was clean and smelled wonderful, great views, plenty of room, and the bonus part was the fish was biting right off our private dock in the backyard, the host Pamela was great"
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
Beautiful 3,000 SF Castle in the Vineyards
9.8 out of 10, Exceptional, 190 reviews
"Great location for day trips, north, south, east or west. Plenty of room won't be on top of each other. Michael gives great suggestion, I would strongly recommend. Kitchen full stocked for cooking."
Beautiful 3,000 SF Castle in the Vineyards
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, 211 reviews
"I stayed at Jim’s house during my wedding weekend with a few of my groomsmen and their partners. Big weekend for me obviously, and this house certainly contributed to it living up to the hype. We were welcomed with some snacks, wine, and a fridge full of beverages to our surprise—thanks again Jim! The property itself is beautiful, with great views of the vineyards and tons of areas to sit and lounge outside. The wraparound porch was awesome for hanging out too when we got bit too toasty...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
8.8 out of 10, Excellent, 134 reviews
"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!
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
9.6 out of 10, Exceptional, 12 reviews
"We enjoyed the house very much! Backyard was great for cocktails and relaxing. The host was very responsive. Clean and well kept."
The price is €1,600
includes taxes & fees
25 Jun - 26 Jun
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Great Price! Sunset Beach House private beach, firepits, hottub, dock, & more!
10.0 out of 10, Exceptional, 98 reviews
"Everything was great!"
Great Price! Sunset Beach House private beach, firepits, hottub, dock, & more!
Sunny View Cottage in the Beautiful Wine Country
10.0 out of 10, Exceptional, 247 reviews
"Very nice & peaceful"
Sunny View Cottage in the Beautiful Wine Country
Home near Sonoma & Calistoga in heart of Wine Country
9.6 out of 10, Exceptional, 22 reviews
"Thank you for the clean, quiet place to land"
Home near Sonoma & Calistoga in heart of Wine Country
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
9.8 out of 10, Exceptional, 78 reviews
"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, 1,823 reviews
"Loved our room. Bathroom seemed to have been newly renovated and was really nice and clean. The whole place was clean. Bed was comfortable. Front desk staff were all nice. Was excited to find a Trader Joe's so close by."
The price is €128
includes taxes & fees
24 Jun - 25 Jun
The Sandman Hotel
Hyatt Regency Sonoma Wine Country
4.0 star property
8.2 out of 10, Very good, 1,015 reviews
"Excellent location Beats the courtyard "
The price is €218
includes taxes & fees
7 Jul - 8 Jul
Hyatt Regency Sonoma Wine Country
Flamingo Resort & Spa
4.0 star property
7.8 out of 10, Good, 1,008 reviews
"Perfect place to stay for Country Summer Event!"
The price is €228
includes taxes & fees
25 Jun - 26 Jun
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.

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, apart-hotels, 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 favorite 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 depends 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 €166 per night. Entering your travel dates in the search wizard you might find 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?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This holiday home rental outside of Middletown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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