Photo by Shannon Willitts

Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (42)
"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "
The price is €206
includes taxes & fees
19 Feb - 20 Feb
Backyard Garden Oasis

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (295)
"It was clean, quiet and all requirements met. "
The price is €137
includes taxes & fees
19 Feb - 20 Feb
Clear Lake Cottages & Marina

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

10.0 out of 10, Exceptional, (219)
"Lavender Hill was the perfect spot for a weekend reunion with a bunch of friends to celebrate a milestone birthday! The home is beautiful and has everything you need for a great stay. The panoramic views were breathtaking and our group spent the majority of our stay in the living area soaking up the beauty. We had grand plans for making more use of the sport court and would've loved to use the pool (it was too cold), but this just makes it easier to plan a return stay in the future. Thanks to...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (22)
"We loved our 2-night stay. We especially loved that each person in our group had their own bedroom (and bathroom). The house is beautifully designed with comfortable beds and couches. The living/dining room has gorgeous massive ceilings. We also loved the huge dining table for meals/games, etc. The aesthetic throughout the house was right up the alley of our group. Everything you need is provided and has been thoughtfully curated. Every room was well-appointed and very clean.The hot tub...
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country

10.0 out of 10, Exceptional, (78)
"This is a lovely property with a great location! Great communication with property manager. Would definitely stay again!"
Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (236)
"Great friends, great house, great memories!We could not have asked for more."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

10.0 out of 10, Exceptional, (234)
"The home was wonderful and the property so relaxing and beautiful. We look forward to staying here again! Thank you so much Kristen for all your help as the property manager. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

Calistoga Vineyard House

10.0 out of 10, Exceptional, (34)
"Nice new place with great kitchen."
Calistoga Vineyard House

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

10.0 out of 10, Exceptional, (222)
"This is a beautiful home in a quaint location to build special memories. We will definitely return!!"
The price is €1,996
includes taxes & fees
17 Mar - 18 Mar
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Luxury Napa Valley Estate Surrounded by Vineyards

9.8 out of 10, Exceptional, (29)
"Staying at the Vine and Rose was an amazing experience! We had a terrific dinner party at the massive dining table to celebrate a 60th Birthday and wonderful friends to enjoy the property with. The rooms were great, the kitchen is an awesome hang out spot, and the property has so many things to do that you don't want to leave. We highly recommend this property!"
Luxury Napa Valley Estate Surrounded by Vineyards

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

10.0 out of 10, Exceptional, (113)
"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

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

10.0 out of 10, Exceptional, (144)
"Beautiful setting with a wonderful home. Loved the location near Healdsburg. Everything was convenient. The property manager was fantastic!"
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (69)
"Very private large house and yard perfect!"
Wine Country Harvest Vacation Home

Vineyard and garden views, large open kitchen Space for play and meditaion

10.0 out of 10, Exceptional, (84)
"My family of four (two teenagers) and my brother and sister-in-law hand a wonderful stay over New Years Eve and Day. The location was convenient, quiet, with great views. We loved the modern kitchen, extremely well equipped, enjoyed the garden, and made for an amazing place to enjoy the wine country and just being lazy and enjoying the surrounding hills and scenery. Home has a great modern design with upscale finishes. "
Vineyard and garden views, large open kitchen Space for play and meditaion

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

10.0 out of 10, Exceptional, (127)
"Don’t hesitate to book this place! Amazing 360 views, gorgeous house that’s even bigger and nicer than the photos. The owner Per is super nice and communicative. Everything in the house is top of the line. We loved it!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

The St. Helena House

10.0 out of 10, Exceptional, (224)
"An amazing house inside and out - Jim was wonderful to work with and hope to return someday!"
The St. Helena House

1 Block To St. Helena Main Street Shops-Restaurants! Avail Jan 20-Feb 2, 10-16

10.0 out of 10, Exceptional, (246)
"Fanatic house just a short walk to so much in st Helena. Fabulous stay. Thank you "
The price is €1,325
includes taxes & fees
19 Feb - 20 Feb
1 Block To St. Helena Main Street Shops-Restaurants! Avail Jan 20-Feb 2, 10-16

Napa Valley: St Helena Designer Home & Guest House + Spool + Peloton Bike/Tread

10.0 out of 10, Exceptional, (111)
"Ideal location in St. Helena to use a base for wine tasting. Everything you need is walking distance. "
Napa Valley: St Helena Designer Home & Guest House + Spool + Peloton Bike/Tread

Mandala Springs Wellness Retreat Center

3.5 star property
8.6 out of 10, Excellent, (27)
"I loved the cottage I stayed in! Having a kitchenette, porch, A/C were awesome! The only issues were; no screen on door; shower curtain rings wouldn't stay in place. Also fun were mini-golf, badminton, hot tub, pool, paddle boat. Thank you!!! Cheryl M. & her sister Janine "
The price is €240
includes taxes & fees
3 Mar - 4 Mar
Mandala Springs Wellness Retreat Center

Wine Country Backyard Escape

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay! The backyard was perfect for eating outside, relaxing in the hot tub and playing bocce. Our little dogs loved the freedom to run and play in the fenced yard."
Wine Country Backyard Escape
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
8.4 out of 10, Very good, (2043)
"Super cute hotel. Quiet area with a fun pool/bar area. "
The price is €80
includes taxes & fees
24 Feb - 25 Feb
The Sandman Hotel

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 star property
9.2 out of 10, Wonderful, (1016)
"Very clean"
The price is €116
includes taxes & fees
21 Feb - 22 Feb
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Flamingo Resort & Spa

4.0 star property
8.0 out of 10, Very good, (1008)
"I has good service and good experience "
The price is €153
includes taxes & fees
23 Feb - 24 Feb
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?

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley: This holiday home rental outside of Middletown offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

Expedia has 7 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.