Photo by Shannon Willitts

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, (292)
"The property itself is beautiful, peaceful and a safe place to walk around. The area surrounding and driving through to get to the property is another story. We stayed Lakefront , so beautiful! We will stay again! "
The price is NZ$257
includes taxes & fees
5 Jan - 6 Jan
Clear Lake Cottages & Marina

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (221)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is NZ$3,766
includes taxes & fees
2 Feb - 3 Feb
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

The St. Helena House

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (67)
"Very niche home with plenty of space inside and out. Lots of space to gather. Convenient location close to grocery shopping and restaurants. "
Wine Country Harvest Vacation Home

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (215)
"Our stay at the Kenwood country estate was a wonderful and memorable experience! The property was private and secluded and exactly as listed. We stayed over Thanksgiving week and although our food was catered, we found all the entertaining essentials to complement our meal and make us feel right at home. The weather was warm, so we were able to join in the local Turkey Trot, play pickle ball on the well equipped courts, ride bikes on local trails, and enjoy morning yoga while taking in the...
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, (125)
"This house has everything and comes well stocked! Love that each bedroom has a king bed and its own bathroom! It’s perfect for groups! The kitchen was well stocked with platters, drink ware, bar essentials, etc. Also, the views are spectacular! We loved our stay! "
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Luxury Napa Valley Estate Surrounded by Vineyards

9.8 out of 10, Exceptional, (27)
"Perfect location, perfect place. Property is simply amazing. Could not pick a more beautiful location. The property is located on a vineyard and is incredibly peaceful. "
Luxury Napa Valley Estate Surrounded by Vineyards

Secluded home with private saltwater pool, spa & amazing view - dog-friendly

8.8 out of 10, Excellent, (21)
"Nice, clean house, great views"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (39)
"Great place to stay. Conveniently located for our needs."
The price is NZ$407
includes taxes & fees
5 Jan - 6 Jan
Comfort and Style in Our Queen Cottage

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (39)
"This is the second time that we have stayed at Chanric and we have really enjoyed it both times. It is beautiful, updated, clean, well equipped, and well managed. The property manager was accessible, friendly, and helpful. We have been to Napa with various groups many times, but this is where we will stay on future trips!"
The price is NZ$3,068
includes taxes & fees
22 Jan - 23 Jan
Luxury Napa Estate With Pool/Hot-tub/Concierge

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

10.0 out of 10, Exceptional, (154)
"My family and I stayed here for the Thanksgiving holiday and had an absolutely wonderful stay. The place is well equipped and very cozy with a wood burning fireplace, beautiful outdoor spaces (including multiple fire pits) and comfortable bedrooms. The host is also amazing - communication before, during and after was easy and included fantastic recommendations. And to top it all off, they even treated my family and I to a complimentary tasting at a local winery. Would definitely recommend!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

10.0 out of 10, Exceptional, (19)
"We were in Napa Valley for a special event with Truffle Shuffle at the Charles Krug vineyard. This home was in the perfect location to attend our event. Everything was as stated in the listing, and Arturo was very responsive to all our needs. We had one minor issue; he was all over it and corrected it immediately. I highly recommend this location. We had three couples, and this home accommodated us perfectly."
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

1 Acre with 3 homes in the heart of wine country with last minute specials!

9.6 out of 10, Exceptional, (28)
"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "
1 Acre with 3 homes in the heart of wine country with last minute specials!

Stunning retreat with private hot tub, firepit & 1 acre of country charm

9.2 out of 10, Wonderful, (71)
"4 sisters and nieces together for mini vacations in wine country. We love the location and the property."
Stunning retreat with private hot tub, firepit & 1 acre of country charm

Beautiful 3,000 SF Castle in the Vineyards

9.8 out of 10, Exceptional, (200)
"What a wonderful place to get away. Michael, the host was so friendly and told us the history of the castle. This was a four day getaway with friends and we would love to go back as soon as possible. The home was warm and cozy very unique. The amenities were perfect. first class beddings something you would expect in a five star hotel. Great kitchen with everything you can possibly need to prepare a meal.. We can’t wait to go back!"
Beautiful 3,000 SF Castle in the Vineyards

Elegant five-acre estate with mountain view, W/D, & pond - close to wineries

8.4 out of 10, Very good, (74)
"Loved the large property. "
Elegant five-acre estate with mountain view, W/D, & pond - close to wineries

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

10.0 out of 10, Exceptional, (182)
"Well appointed comfortable small house in Kenwood. Nothing fancy, but well looked after and with a very responsive host who lives about an hour away. Nice field at a park nearby that is least free until 9 o’clock."
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (30)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
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, (85)
"The home was located in a beautiful area. Lots of great shops and restaurants within walking distance."
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
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.
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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, (2001)
"Stayed one night and this place was so perfect!! Clean room and bathroom, the pool and hot tub were so nice. We checked in late and the gave us a late check out. Such a luxury, we loved this place!"
The price is NZ$166
includes taxes & fees
7 Jan - 8 Jan
The Sandman Hotel

Flamingo Resort & Spa

4.0 star property
8.0 out of 10, Very good, (1003)
"Very cute property with lots of action. Difficult to get into restaurant since it’s always booked"
The price is NZ$273
includes taxes & fees
5 Jan - 6 Jan
Flamingo Resort & Spa

Hyatt Regency Sonoma Wine Country

4.0 star property
8.2 out of 10, Very good, (1004)
"Clean room, and friendly staff "
The price is NZ$286
includes taxes & fees
9 Jan - 10 Jan
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.

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 6 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.