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Compare 644 Vacation Homes in Middletown with updated reviews, rates, and availability.

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (72)
"Clean, spacious, and comfortable home. Behind the backyard fence is road so traffic can sound noisy at times. The morning was peaceful though wrong birds singing and a river water sound flowing. Beds and couch were comfortable.Somethings to know about the house. It was difficult to get to. Maps took us to the street behind the house and the road is fenced off and unable to turn in. So we had to take a road then turn on to the house road. The door did not lock when we closed it, you need to press...
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

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

10.0 out of 10, Exceptional, (14)
"Great place!! "
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Cozy Cottage: Panoramic Lake Views, WiFi, Deck

The price is SAR 469
SAR 750 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

10.0 out of 10, Exceptional, (187)
"Maison Jacqueline was the perfect locale for our (senior) girls’ getaway! This charming and comfortable home had everything we needed to relax and unwind while exploring Sonoma and Napa. Owner Jackie was so easy to deal with! This is a perfect spot for a wine country holiday."
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

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

10.0 out of 10, Exceptional, (120)
"Perfect place to stay for close proximity to everything Napa Valley. Walking distance to downtown St Helena. Very comfortable accommodations. Well appointed and very functional kitchen. We loved our stay and hope to be back soon. "
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

1 Block To St. Helena Main Street Shops-Restaurants! Avail April 19-29,May 13-17

10.0 out of 10, Exceptional, (251)
"We wanted place walking distance to tastings and restaurants. House hit that and much more. Three couples stayed so having king beds in all bedrooms were great. Also loved the outdoor space. Would like to stay again. "
1 Block To St. Helena Main Street Shops-Restaurants! Avail April 19-29,May 13-17

Custom Winemaker's home - WALKING distance to 9 wineries! This is the place.

10.0 out of 10, Exceptional, (96)
"We absolutely loved our stay in Kenwood. We enjoyed all the nearby wineries, and also loved being located between Sonoma and Santa Rosa (and closer to Guerneville, Healdsburg, and Bodega Bay). We hiked nearly every day as we had a variety of choices nearby. The house had everything we wanted or needed, and our communication with the owner was always friendly, quick, and easy. One of our favorite places we've stayed!"
Custom Winemaker's home - WALKING distance to 9 wineries! This is the place.

The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

10.0 out of 10, Exceptional, (59)
"My spouse and I wanted to stay in this area to stargaze with our basic telescope. The cottage has a beautiful view of the sky. A couple of bowls in the cupboard has been put away without being cleaned first, but our stay was otherwise great. Nicole was very responsive and kind."
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

The Sonoma Valley Cottage

10.0 out of 10, Exceptional, (12)
"It's a great property in a good location. Good kitchen and bedrooms, very comfortable beds. Very minor suggestions: some hooks or towel rods in the bathrooms would be helpful, we were surprised they weren't there in the master bathroom. Some stoppers for this sinks would be helpful too."
The price is SAR 1,473
SAR 2,688 total
includes taxes & fees
19 Apr - 20 Apr
The Sonoma Valley Cottage

Cozy Woodland Escape, Hot Tub, Redwood + Water Views, mins from spas in Napa

9.6 out of 10, Exceptional, (30)
"Very clean. Was perfect for our needs. Especially loved the chickens!"
Cozy Woodland Escape, Hot Tub, Redwood + Water Views, mins from spas in Napa

Wine Country Get Away

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at this property. The location is quiet, yet fairly close to stores and restaurants. The beds are soft but comfortable and the living room accommodated the 2 of us quite well. Kitchen had what we needed. It was nice to sit in the backyard. I do wish the lighting in the bedrooms and second bathroom was brighter. "
The price is SAR 634
SAR 1,657 total
includes taxes & fees
19 Apr - 20 Apr
Wine Country Get Away

Cobb Mountain Chalet Main For

9.6 out of 10, Exceptional, (13)
"We had an amazing stay at this property! The house was clean, well-maintained, and equipped with all the basic necessities we needed. The best part was that it was only a 7-minute walk to a family member’s new home in Cobb, which made it incredibly convenient. We will definitely be staying here again on our next visit!Thank you for making our stay so enjoyable!"
The price is SAR 338
SAR 683 total
includes taxes & fees
21 Apr - 22 Apr
Cobb Mountain Chalet Main For

Tropical Lakefront Retreat with Private Dock & Kayaks

9.8 out of 10, Exceptional, (74)
"Our family had an absolute amazing stay at this lake house. Love that we could keep our boat in the water the whole weekend. Even though the weather was not great for our spring break trip.. I am happy we were able to stay in and enjoy this very cozy home when the weather was not in our favor. There is a pool table and WII for the kids to play with and a ton of outdoor space.. loved the fire pits and I can only imagine visiting in the warmer months. We will definitely be back. Thanks for sharing...
Tropical Lakefront Retreat with Private Dock & Kayaks

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

9.8 out of 10, Exceptional, (26)
"The house worked perfectly for our group"
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

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

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

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!

Wine Country Lux Villa w/ Hot Tub and Pool

10.0 out of 10, Exceptional, (13)
"We loved the spacing of the rooms, the bathrooms, and the common areas. The property is beautiful and the host was very responsive. Highly recommend. "
The price is SAR 4,127
SAR 5,913 total
includes taxes & fees
23 Apr - 24 Apr
Wine Country Lux Villa w/ Hot Tub and Pool

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

9.6 out of 10, Exceptional, (53)
"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 SAR 559
SAR 1,434 total
includes taxes & fees
18 May - 19 May
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
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

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (43)
"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 SAR 728
SAR 812 total
includes taxes & fees
21 Apr - 22 Apr
Backyard Garden Oasis

Calistoga Creek Side Mountain Estate

9.6 out of 10, Exceptional, (4)
"Absolutely perfect for our work retreat! Such a gem of a place."
Calistoga Creek Side Mountain Estate

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (301)
"Stayed here many times and always happy! "
The price is SAR 485
SAR 541 total
includes taxes & fees
22 Apr - 23 Apr
Clear Lake Cottages & Marina
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.