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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Clear Lake Cottages & Marina
View from property
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
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
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 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
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
Pool | Outdoor pool, a heated pool
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
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Safari West
Exterior
Safari West
2.0 star property
9.4 out of 10, Exceptional, 219 reviews
"Incredible experience!"
The price is ￥63,529
￥72,423 total
includes taxes & fees
May 31 - Jun 1
Safari West
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
4 bedrooms, WiFi, bed sheets
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!
Property grounds
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 ￥59,115
￥113,364 total
includes taxes & fees
Jun 27 - Jun 28
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
Stunning retreat with private hot tub, firepit & 1 acre of country charm
Fridge, microwave, oven, stovetop
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
Cottage home near the Russian River; county parks; numerous wineries
Property grounds
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
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Interior
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 ￥259,430
￥330,812 total
includes taxes & fees
Jun 2 - Jun 3
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Property grounds
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, 158 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
Fridge, microwave, oven, stovetop
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
Property grounds
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
Sunny View Cottage in the Beautiful Wine Country
Fridge, microwave, oven, stovetop
Sunny View Cottage in the Beautiful Wine Country
10.0 out of 10, Exceptional, 246 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
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
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 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
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
Outdoor pool
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
10.0 out of 10, Exceptional, 68 reviews
"We have visited Healdsburg for years, because of the house, this was our best trip. The home was incredibly comfortable and perfectly situated for wine tasting."
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
Luxury Napa Estate With Pool/Hot-tub/Concierge
Property grounds
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
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
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, 96 reviews
"Great location. Super clean. Super efficient. Super comfortable. Well appointed home. Smart and responsive host. Friendly and accommodating. We’ll be back!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
Pool
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.4 out of 10, Very Good, 12 reviews
"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
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Property grounds
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 ￥102,466
￥198,942 total
includes taxes & fees
Jun 4 - Jun 5
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, 200 reviews
"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
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.

Other types of properties in Middletown you may be interested in

The Sandman Hotel
Lobby lounge
The Sandman Hotel
3.0 star property
8.2 out of 10, Very Good, 1,776 reviews
"I like the room nice and clean "
The price is ￥18,967
￥21,660 total
includes taxes & fees
Jun 5 - Jun 6
The Sandman Hotel
Hyatt Regency Sonoma Wine Country
Breakfast served
Hyatt Regency Sonoma Wine Country
4.0 star property
8.2 out of 10, Very Good, 1,005 reviews
"The buffet breakfast was excellant"
The price is ￥26,531
￥36,625 total
includes taxes & fees
Jun 24 - Jun 25
Hyatt Regency Sonoma Wine Country
Flamingo Resort & Spa
Lunch served, pool views
Flamingo Resort & Spa
4.0 star property
7.8 out of 10, Good, 1,003 reviews
"Love staying here checking in and out was a breeze. "
The price is ￥26,605
￥36,682 total
includes taxes & fees
Jun 16 - Jun 17
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.

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

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. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

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

Hotel La Rose

Hotel La Rose

5/5 Excellent
Nice Historic Hotel
"This is a nice historic boutique hotel. It is close to shopping, a nice coffee shop and the train station. "
A verified traveler stayed at Hotel La Rose
Posted 1 day ago
Hotel La Rose