Photo by Shannon Willitts

Middletown Holiday Rentals

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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 NZ$379
includes taxes & fees
18 Apr - 19 Apr
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 NZ$272
includes taxes & fees
7 Apr - 8 Apr
Clear Lake Cottages & Marina

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (71)
"Clean, centrally located in quiet neighborhood. Coffee pot needs replaced. Cleaning person still cleaning when we arrived and was waiting before check out time the day we left. Aside from that, great place. Outdoor living area and being able to bring a dog were appreciated!"
The price is NZ$2,056
includes taxes & fees
26 Apr - 27 Apr
Wine Country Harvest Vacation Home

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

10.0 out of 10, Exceptional, (220)
"This is our second time renting Willian's home in Kenwood. This home is absolutely stunning and fully equipped with everything you need for a family or group of friends gathering. Fold-out bunk beds, 3 pack and plays, a high chair, tennis and pickle ball rackets, sidewalk chalk and great kitchen and bathroom products. Linens are great quality as well. Chateau St Jean and many other wineries are minutes away. We will absolutely rent this home again and will recommend it to others.Only issue is...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

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

10.0 out of 10, Exceptional, (119)
"Great private home among the vineyard. 10 min walk to St Helena. Highly recommended. "
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (13)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is NZ$656
includes taxes & fees
8 Apr - 9 Apr
Escape to Wine County in your independant Cottage in Downtown Calistoga

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

10.0 out of 10, Exceptional, (284)
"Booked the cabin as it was near Healdsburg and several favorite wineries. It couldn't have been more perfect - cabin was even better than it looked in the photos. Everything we needed was there waiting for us, complete with welcoming flowers on the counter. The owner responded to a couple questions very quickly and also sent us a lot of info about the area. Definitely hope to return and stay here again. Thanks for everything!"
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (41)
"Nice location and space was very comfortable"
The price is NZ$399
includes taxes & fees
6 Apr - 7 Apr
Comfort and Style in Our Queen Cottage

Renovated Vineyard Home - 4 BR/4 BA - Solar 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!"
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

Pool Paradise in Wine Country!

3.0 star property
10.0 out of 10, Exceptional, (5)
"The property was well appointed with everything we could need for our stay and the hot tub was great, as was the game room. Beds were comfy and the couches and blankets fit all 7 of us. Small blemishes here and there was well as some general maintenance needed on the deck / interior, but nothing out of the ordinary for a house like this. Overall very enjoyable stay for the entire extended family."
Pool Paradise in Wine Country!

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

10.0 out of 10, Exceptional, (223)
"This was my second time at this house - it is beautiful and perfectly set up for a larger group (6-12 people), with lots of privacy for all. The front porch looking over the front yard vines and the back patio were wonderful places to gather and hang out. The house has all the amenities you need - the kitchen is well set up. The hosts' instructions for checking in and out were clear. The location is ideal - easy to walk to and down Main Street in St Helena. We brought in fresh baked goods...
The price is NZ$3,677
includes taxes & fees
10 Apr - 11 Apr
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (42)
"Exactly as described and pictured - beautiful property, clean, quiet, comfortable bedding, updated throughout. Gem!"
The price is NZ$3,853
includes taxes & fees
7 Apr - 8 Apr
Luxury Napa Estate With Pool/Hot-tub/Concierge

Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019

9.8 out of 10, Exceptional, (86)
"The home is in a nice St Helena location about a half mile north of downtown and just south of Beringer. The only complaint about location was road noise. If we had gotten the Sonos speaker to work might have made it better but it did wake us up in early AM. Having 3 bedrooms was a requirement but otherwise I probably wouldn’t have stayed because off season the price was high for not really being able to use the backyard. The Iayout was great. We enjoyed breakfast at the dining table with view...
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019

Luxury Napa Valley Estate Surrounded by Vineyards

9.8 out of 10, Exceptional, (30)
"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

Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

9.6 out of 10, Exceptional, (52)
"The view is amazing. The road to get there is confusing and very windy and narrow. There is very little in the kitchen so bring everything you need. There is a coffee maker with filters and literally salt and ice. Period.Steep driveway steep stairs. Only one bathroom. Comfy beds"
The price is NZ$671
includes taxes & fees
16 Apr - 17 Apr
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

Calistoga Vineyard House

10.0 out of 10, Exceptional, (38)
"Our stay in the beautiful Napa valley was so enhanced by staying at this VRBO rental. The house was well appointed with all the latest in decor, amazing views, and special touches that made us feel welcomed. I was celebrating my birthday and the host left a bottle of champagne in the fridge, plus cute party hats to celebrate with. The location couldn’t have been more ideal, only few minutes drive to get into town and yet it felt totally private. Highly recommend this fabulous property."
Calistoga Vineyard House

Direct Lake Front Paradise Cove #1 In Reviews - Beach - Launch - Traeger Smoker

9.8 out of 10, Exceptional, (187)
"Greg and Jennifer’s house is so lovely and peaceful. It was just what we were looking for. The house is well kept and labeled so we had absolutely no guess work the whole time. They’re kind enough to leave plenty of pellets to smoke a meal. The beds were so comfy. Even when it rained we were able to bird watch from the large windows and watch all the wildlife right from the couch. When the rain would pass we’d sit out at their large table and enjoyed the sun while the dogs splashed in the water....
Direct Lake Front Paradise Cove #1 In Reviews - Beach - Launch - Traeger Smoker

Secluded Wine Country Luxury | Vineyard Views, Saltwater Pool, Sauna, Game Room

Secluded Wine Country Luxury | Vineyard Views, Saltwater Pool, Sauna, Game Room

St. Helena estate, in heart of the Napa wine country, walk to town, on vineyard

10.0 out of 10, Exceptional, (99)
"The home was warm and inviting. Plenty of outdoor space to enjoy and just lovely overall. Indoor space was very roomy and nice. Overall a great place to stay."
St. Helena estate, in heart of the Napa wine country, walk to town, on vineyard

7BD/4.5BA Santa Rosa Estate w/ HotTub, Games, BBQ!

The price is NZ$3,545
includes taxes & fees
7 Apr - 8 Apr
7BD/4.5BA Santa Rosa Estate w/ HotTub, Games, BBQ!
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 Santa Rosa Sonoma, Ascend Hotel Collection

3.0 star property
8.4 out of 10, Very good, (2085)
"Our stay was good. The bed was very comfortable, the room was big and clean. It was also very quiet. Good value for the money. "
The price is NZ$154
includes taxes & fees
20 Apr - 21 Apr
The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

Holiday Inn Windsor Wine Country by IHG

3.0 star property
9.0 out of 10, Wonderful, (933)
"Nice hotel for the price. We did not like the shower at all. The water pressure was horrible and the water never got hot."
The price is NZ$206
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Windsor Wine Country by IHG

Flamingo Resort & Spa

4.0 star property
8.0 out of 10, Very good, (1013)
"Our stay was amazing. We loved the staff, amenities, the cleanliness, the beautiful property, its history, and more. This was the perfect stay for many members of our families for my and my wife’s wedding weekend! Thank you for a wonderful stay!"
The price is NZ$306
includes taxes & fees
27 Apr - 28 Apr
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?

Wine Country Harvest Vacation Home: This holiday home rental outside of Middletown offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

Expedia has 8 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as Calistoga Spit N' Cycle, or get out into nature at a spot like Boggs Mountain Demonstration State Forest. 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.