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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, (288)
"Very clean"
The price is NZ$265
includes taxes & fees
27 Nov - 28 Nov
Clear Lake Cottages & Marina

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

10.0 out of 10, Exceptional, (222)
"We wanted to introduce friends from East Coast to the Napa Valley- history to modern day. This rare restored farmhouse with views of vineyards was ideal. Authentic, comfortable (with just the right amount of modern amenities but not too much to destroy the charm), spacious, wonderfully furnished, with superb kitchen (fully stocked), and screened porches, etc. The hosts were easy to communicate with and would stay again in a heartbeat. We have stayed at 60+ rentals around the world... this unique...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

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

10.0 out of 10, Exceptional, (219)
"The house was great and the location is super! The sound system in the house was a little challenging for us "old folks", but we made it work!! Would go back again for sure!"
The price is NZ$3,599
includes taxes & fees
1 Dec - 2 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

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

10.0 out of 10, Exceptional, (211)
"We enjoyed our stay at the home. The panoramic windows in the living area provided wonderful views of the valley and wildlife. It was very well stocked and restful!"
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (65)
"Comfortable home with beautiful backyard grill, fire pit and hot tub. Kitchen was well equipped, very clean. Communication with management was prompt and courteous. Our only complaint is that the outdoor living space backed up to a noisy road"
The price is NZ$1,576
includes taxes & fees
30 Nov - 1 Dec
Wine Country Harvest Vacation Home

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

10.0 out of 10, Exceptional, (181)
"We had the best time at this cute rental property. It was comfortable, cute and felt private. This place is perfect for a group and is equipped with anything you might need. We cooked in the kitchen one evening and were in a good spot to tour Healdsburg one day and wineries in Sonoma the next. Would stay again and recommend to friends and family. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

Luxury Napa Valley Estate Surrounded by Vineyards

9.8 out of 10, Exceptional, (26)
"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

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

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

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

8.6 out of 10, Excellent, (73)
"Loved the large property. "
Elegant five-acre estate with mountain view, W/D, & pond - close to wineries

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

10.0 out of 10, Exceptional, (153)
"The cottage and the grounds are absolutely gorgeous! We loved the way the cottage was decorated, so cozy! Everything was well appointed. There are multiple places on the grounds to sit and enjoy a glass of wine and the scenery. It is the perfect size for two couples. The location is close to downtown Healdsburg, Dry Creek wineries and a five-minute walk to the Dry Creek General Store! Napa is only a little over an hour away. The owners and property manager responded quickly when we had...
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

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

10.0 out of 10, Exceptional, (91)
"The property was very good and met all our needs with a couple of exceptions. The bathroom towels were not good, a little smelly and really need to be upgraded along with the toilet paper!"
Cottage home near the Russian River; county parks; numerous wineries

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

Walk to Restaurants, Wineries and More

10.0 out of 10, Exceptional, (206)
"The place was very clean. It had all the necessities you would need for your stay! Walking distance to all restaurants and a few wineries that are near downtown! "
Walk to Restaurants, Wineries and More

1 Block To St. Helena Main Street Shops-Restaurants! Avail Dec 2-5, 8-12 Jan 2-5

10.0 out of 10, Exceptional, (242)
"Close to restaurants & property is lovely. Beautiful backyard!"
1 Block To St. Helena Main Street Shops-Restaurants! Avail Dec 2-5, 8-12 Jan 2-5

3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

10.0 out of 10, Exceptional, (111)
"Our family had an amazing stay in Kirsten's beautiful home in St. Helena. The house was in a great location that is in the middle of everything. Close to the shops and stores of downtown St. Helena and in the middle of the valley so that wineries are close by whether they are up valley towards Calistoga or down towards downtown Napa. The home is well appointed (and beautifully furnished!) and was very comfortable for our 3 couples. Kirsten was very communicative both before and during our...
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

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

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$388
includes taxes & fees
24 Nov - 25 Nov
Comfort and Style in Our Queen Cottage

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

10.0 out of 10, Exceptional, (122)
"Casa Loma is a spectacular property. Definitely the best vrbo propert I have experienced."
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (156)
"This property is exactly as promised. It’s located in such a beautiful area of Healdsburg. If you’re looking for a quiet getaway this is the place for you!"
Newly Refurbished! Nest Cottage at ru's Farm.
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, (1980)
"So clean and very welcoming!"
The price is NZ$154
includes taxes & fees
25 Nov - 26 Nov
The Sandman Hotel

Flamingo Resort & Spa

4.0 star property
8.0 out of 10, Very good, (1001)
"I really like the location, less than 5 min from my mom. It is cute and retro and usually very clean and quiet."
The price is NZ$269
includes taxes & fees
24 Nov - 25 Nov
Flamingo Resort & Spa

Harvest Inn

4.5 star property
9.4 out of 10, Exceptional, (1003)
"The service "
The price is NZ$470
includes taxes & fees
2 Dec - 3 Dec
Harvest Inn
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.
Beautiful view of the beach with palm trees

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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?

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018: 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 3 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?

Boggs Mountain Demonstration State Forest and Robert Louis Stevenson State Park 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.