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Middletown Vacation Rentals

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Vacation Rentals in Middletown

1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, 230 reviews
"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
Safari West
2.0 star property
9.4 out of 10, Exceptional, 219 reviews
"Incredible experience!"
The price is CA $647
CA $738 total
includes taxes & fees
Jun 4 - Jun 5
Safari West
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! "
Clear Lake Cottages & Marina
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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
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, 198 reviews
"This property is amazing and conveniently located."
The price is CA $2,249
CA $2,884 total
includes taxes & fees
Jun 5 - Jun 6
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
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
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"
The price is CA $513
CA $984 total
includes taxes & fees
Jun 27 - Jun 28
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, 79 reviews
"Our family had a wedding to attend in the area and the accommodations were perfect for us! Close to everything. We appreciated having some staples available too (coffee!). Would stay there again for sure!"
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, 64 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, 113 reviews
"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
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!
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.4 out of 10, Very good, 12 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
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, 159 reviews
"What a relaxing stay in Kenwood. Such a cute, comfortable house with a beautiful yard and patio area. I was traveling with my dogs and they loved the fenced in yard. Everything was great!"
Charming Country Home Nestled In Kenwood Village the heart of the 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
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, 209 reviews
"The peace, serenity, and splendor of your house was perfect. Our stay will be long remembered. Thank you for your hospitality! As a bonus, the house was marvelously fit out for the times we elected to stay in and cook!"
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Luxury Napa Estate With Pool/Hot-tub/Concierge
10.0 out of 10, Exceptional, 28 reviews
"Thank you so much for our stay in your beautiful house in Calistoga. It was everything it was advertised to be. It accommodated our family of 12 ranging from 9 months to 66 with ease. Perfect setup, the grounds were beautiful, communication and support were excellent, and convenience to Calistoga and Triple S Ranch could not have been better. It was clean and our daily cleaning service was fantastic. Thank you for everything. Our family vacation was so enjoyable, thanks to you."
Luxury Napa Estate With Pool/Hot-tub/Concierge
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 CA $876
CA $1,710 total
includes taxes & fees
Jun 4 - Jun 5
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Beautiful 3,000 SF Castle in the Vineyards
9.8 out of 10, Exceptional, 189 reviews
"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
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, 148 reviews
"We love staying at this property in Dry Creek! It is so clean and has everything you'd want.. the location is perfect, right in the middle of everything Dry Creek and Healdsburg."
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Sunny View Cottage in the Beautiful Wine Country
10.0 out of 10, Exceptional, 247 reviews
"Sunny View Cottage is comfortable, well-equipped, and charming. The location is quiet and rural but very close to great wineries, restaurants (we loved Walter Hansel’s Bistro, just around the corner), and hiking/biking trails. We would definitely stay here again next time we are in the area."
Sunny View Cottage in the Beautiful Wine Country
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 Vacation Rental Travel Info

Number of vacation rentals
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

The Sandman Hotel
3.0 star property
8.2 out of 10, Very good, 1,779 reviews
"Noisy neighbors. Generally ok."
The price is CA $164
CA $187 total
includes taxes & fees
Jun 9 - Jun 10
The Sandman Hotel
Hyatt Regency Sonoma Wine Country
4.0 star property
8.2 out of 10, Very good, 1,006 reviews
"The buffet breakfast was excellant"
The price is CA $227
CA $314 total
includes taxes & fees
Jul 1 - Jul 2
Hyatt Regency Sonoma Wine Country
Flamingo Resort & Spa
4.0 star property
7.8 out of 10, Good, 1,003 reviews
"Great fun spot! Super pool. Beautiful upkeep. Lovely food."
The price is CA $230
CA $317 total
includes taxes & fees
Jun 26 - Jun 27
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Middletown?

Yes, we offer vacation rentals close to top attractions in Middletown, or you can go with a secluded option if you'd like a relaxing place to 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 vacation rentals that Middletown has to offer?

Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!: This vacation home rental near Middletown is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Middletown?

Expedia has 4 vacation 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 vacation rentals like in Middletown?

Vacation rentals are private properties you can stay in for several days or longer in Middletown. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.

Recent reviews of Middletown properties
Expedia verified reviews