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Compare 506 Vacation Homes in Middletown with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (233)
"We have stayed in properties in many cities. This is one of the finest we have ever experienced. We could not ask for a better vacation home. MMichael "
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

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 Backyard Escape

10.0 out of 10, Exceptional, (13)
"We had two toddlers running around the house and backyard. They loved it. Was a wonderful place for us to relax and enjoy wine country"
Wine Country Backyard Escape

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

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

10.0 out of 10, Exceptional, (217)
"The drive in and out of the property will amaze from the start! The property is wonderfully situated a top a quiet and peaceful Sonoma mountain with fantastic views in all directions. The house is beautifully architected and great for a large group, including the guest house. Game room, hot tub, chef’s kitchen and fire places made for an excellent stay. Kenwood Winery was our fave right near the house. Host was excellent with any questions we had. Our group was super pleased! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

1 Acre with 3 homes in the heart of wine country with last minute specials!

9.6 out of 10, Exceptional, (28)
"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "
1 Acre with 3 homes in the heart of wine country with last minute specials!

Home near golf course, close to Healdsburg

10.0 out of 10, Exceptional, (27)
"Great house and location"
Home near golf course, close to Healdsburg

Casa Rosa Summary:<br>Th

10.0 out of 10, Exceptional, (28)
"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"
Casa Rosa Summary:<br>Th

Calistoga Vineyard House

10.0 out of 10, Exceptional, (33)
"This was a killer place and will be back. "
Calistoga Vineyard House

Annadel House Retreat- Stunning Wine Country Luxe!

9.4 out of 10, Exceptional, (27)
"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...
The price is SAR 1,272
SAR 3,050 total
includes taxes & fees
17 Feb - 18 Feb
Annadel House Retreat- Stunning Wine Country Luxe!

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

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

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

10.0 out of 10, Exceptional, (112)
"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

Walk to Restaurants, Wineries and More

10.0 out of 10, Exceptional, (207)
"nice, clean house. Everything you could need is thoughtfully organized. Close to all, walk to shops, dining and markets. Quiet. Thank you, hope to stay again on our next visit "
Walk to Restaurants, Wineries and More

Home near Sonoma & Calistoga in heart of Wine Country

9.4 out of 10, Exceptional, (35)
"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."
Home near Sonoma & Calistoga in heart of Wine Country

Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

10.0 out of 10, Exceptional, (233)
"This is the perfect place to stay if you want the quiet beauty of the vineyards but the proximity to downtown. Since we were a group of two couples it was really lovely to have two ensuites with king beds. Don’t forget your swimsuit as it’s nice to take advantage of the hot tub, especially at sunset with a glass of wine in your hand."
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

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

The Sonoma Valley Cottage

9.8 out of 10, Exceptional, (7)
"The house was perfect for our family. It was well equipped and very clean and tidy. We had a great time."
The Sonoma Valley Cottage

The St. Helena House

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (67)
"Very niche home with plenty of space inside and out. Lots of space to gather. Convenient location close to grocery shopping and restaurants. "
Wine Country Harvest Vacation Home

Beautiful 3,000 SF Castle in the Vineyards

9.8 out of 10, Exceptional, (201)
"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
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 property types in Middletown

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (294)
"I received an upgraded unit out of the kindness of the owners heart. I was Very Pleased with the unit I stayed 2 nights in.....Very up to date,,,,Very Clean & Comfortable..... I would highly recommend Clear Lake Cottages & Marina to all my friends and family. If you are looking for a good quality,, clean & neat place to stay.....this is the place.... "
The price is SAR 484
SAR 540 total
includes taxes & fees
24 Jan - 25 Jan
Clear Lake Cottages & Marina

The St. Helena House

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House

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
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.