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Compare 508 Vacation Homes in Middletown with updated reviews, rates, and availability.

"This house is immaculately clean, modern, and the location couldn’t be better. Overlooking the rolling hills of the Dry Creek Valley and just minutes to Healdsburg, this is a wonderful property. We will most definitely return for future stays."

"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...

"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."

"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...

"House was perfect for our group size. Everything was perfect. Everyone was comfortable and had space. Kids loved exploring and got tub"

"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!"

"Nice new place with great kitchen."

"This house is wonderful and very comfortable for 4 couples.Location is perfect and can walk to most of the restaurants. We will rent again ! Patty"

"Wow. We loved everything about this place. As comfortable as home. Fantastic location for lots of wineries. Windsor is a cute town. Nothing is very far. Best part was have a waffle maker to make our traditional Christmas morning waffles. Will definitely stay again. "

"We had a fantastic time with five ladies from across the country to celebrate two 50th birthdays. The place was fantastic – the kitchen was great for cooking a meal and for coffee in the morning. Plenty of space to spread out & the beds were comfortable!!!! We had a minor issue with the showerheads being scaled with water. We reached out to the property owner and while they didn’t fix it on our visit 6 pounds of salt were dropped off so I assume they are fixing it for the next guest. Highly...

SAR 3,015 total

includes taxes & fees

25 Feb - 26 Feb

"Property was perfect for me while I was taking care of my grandchildren"

"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...

"Our group of 6 had a great weekend at the property. Beds were comfortable, house was clean, kitchen was well stocked. "

Enjoy lawns, gardens, and a walk in through our vineyards

"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. "

"Ideal location in St. Helena to use a base for wine tasting. Everything you need is walking distance. "

"Simple property in a very quiet neighborhood. It is nothing fancy, but the price compared to everything else I could find for the same date. We needed three rooms with at least a double or larger for a long weekend stay. This fit the bill. The only odd thing to note is that some of the water valves are backwards. It didn't really impact our stay however. We would stay hear again."

"The house is in an amazing location. Walkable to a ton of great food and shops. It’s apparent that the house is well kept as soon as you walk in the door. Everything is clean and fresh. The house feels practically new. Garage shielded the cars from Mother Nature. We had an amazing stay. We will definitely be back!"

"An amazing house inside and out - Jim was wonderful to work with and hope to return someday!"

"This is a lovely property with a great location! Great communication with property manager. Would definitely stay again!"

"We loved the property, the overall comfort and wonderful groundsThe location was what we were looking for and totally enjoyed the whole experience We would recommend to anyone and we would love to rebid and spend more timeThank you so much"