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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, (285)
"Great cottages many of which have beautiful views of the lake and super friendly and efficient staff."
The price is NZ$259
includes taxes & fees
6 Nov - 7 Nov
Clear Lake Cottages & Marina
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (217)
"We all enjoyed the stay. The property was very clean and welcoming. Beds were all comfortable and the kitchen was stocked with all needs. "
The price is NZ$3,529
includes taxes & fees
11 Nov - 12 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (221)
"The property was impecable, the beds and pillows very comfortable and upscale. I would 100% stay there again. Cheers"
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Safari West
2.0 star property
9.4 out of 10, Exceptional, (223)
"The luxury tent was awesome! Arriving to our accommodation after our safari made the experience very cool. You are not able to drive up to the tents but the staff does a good job of transporting your belongings. Having a view of the giraffes, antelope, flamingos was splendid. Overall great experience. "
Safari West
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
Beautiful 3,000 SF Castle in the Vineyards
9.8 out of 10, Exceptional, (198)
"This castle is one of a kind with an interesting and fun history which the host will share Along with many wonderful recommendations of things to do in the area - wine tasting, hiking along the coast and in the redwoods, live music, shopping, restaurants, kayaking "
Beautiful 3,000 SF Castle in the Vineyards
1 Block To St. Helena Main Street Shops-Restaurants! Avail Nov3-7, 16-19,Dec 2-5
10.0 out of 10, Exceptional, (240)
"Fabulous rental experience. The host was very helpful and available if needed. The house was super clean and the back yard was so relaxing. Highly recommend!!!"
1 Block To St. Helena Main Street Shops-Restaurants! Avail Nov3-7, 16-19,Dec 2-5
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
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (179)
"Our host, Jackie, was immediately responsive, helpful, and inviting. The house cute and cozy with plenty of beds and amenities. There is a Safeway and other stores nearby if you need anything else. The house is a bit of a drive from the wineries in St. Helena, but that wasn't anything unexpected. We had never been to Kenwood, and I have to day it's gorgeous! I'd definitely like to visit again in the future. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.8 out of 10, Excellent, (20)
"We absolutely loved the outdoor space. Pool was great, did not feel that he needed additional heating that other guests complained of. I believe we hit it at the right time of year. Great shaded area for guests to sit and hang out. House had all the accommodations/amenities for hosting small gathering. Very comfortable stay and glad to have the AC during summer as it gets quite hot in Cloverdale. Beds were very comfortable. Main floor had a bit of wet dog smell, but overall very clean. Since...
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
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
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$387
includes taxes & fees
6 Nov - 7 Nov
Comfort and Style in Our Queen Cottage
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$1,614
includes taxes & fees
30 Nov - 1 Dec
Wine Country Harvest Vacation Home
Luxury Napa Estate With Pool/Hot-tub/Concierge
10.0 out of 10, Exceptional, (37)
"12 of us really enjoyed the Chanric House! The kitchen is very well stocked but it takes some getting used to with the dishwasher and fridge very low to the ground. Not a real problem though. Grounds are lovely as is pool and hot tub. We cooked all our dinners at home. Saloni was helpful with questions. Esperanza did a great job with housekeeping."
The price is NZ$3,225
includes taxes & fees
2 Dec - 3 Dec
Luxury Napa Estate With Pool/Hot-tub/Concierge
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
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
9.8 out of 10, Exceptional, (84)
"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
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
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
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
10.0 out of 10, Exceptional, (109)
"Excellent experience, starting with the hosts courtesy of allowing an early check-in, the excellent condition and location of the property, which was well equiped and perfectly clean. We couldn’t have made a better choice!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
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
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, (1945)
"Good experience. Nice location, room was clean and updated. "
The price is NZ$145
includes taxes & fees
12 Nov - 13 Nov
The Sandman Hotel
Hyatt Regency Sonoma Wine Country
4.0 star property
8.2 out of 10, Very good, (1001)
"As expected "
The price is NZ$279
includes taxes & fees
1 Dec - 2 Dec
Hyatt Regency Sonoma Wine Country
Flamingo Resort & Spa
4.0 star property
8.0 out of 10, Very good, (1001)
"We loved the vibe and unique aesthetic of the resort. Beautiful layout, great restaurant, and a cute, quirky room. One qualm is that this place is old, and therefore lacking modern insulation. Noise was an issue, we woke up to pounding bass through the paper thin walls. Also, the lack of room service doesn’t match the price or resort feel. The food is delicious though!"
The price is NZ$305
includes taxes & fees
7 Nov - 8 Nov
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.

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?

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.