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Compare 652 Vacation Homes in Middletown with updated reviews, rates, and availability.

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 AED 2,618
AED 4,309 total
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

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 AED 459
AED 735 total
includes taxes & fees
10 Apr - 11 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, (184)
"Fun , lots of things todo nearby , fully equipped accommodation "
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, (118)
"The house was perfect for us group of girls for a few days in Napa. It was centrally located to all the things we had planned and the perfect relaxing vibe to come home to at the end of the day. The check-in process was very easy.The house was perfectly clean, spacious, and had a wonderful front porch and great backyard!We can't wait to stay again."
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 Mar 31-April 10&19-29

10.0 out of 10, Exceptional, (250)
"We had such an amazing week at Jill’s house! The location was so perfect! 5 minutes to farmstead, charter oak, health spa. Gotts, etc. and still a quiet and quaint retreat to come home to. We got married at Farmstead while we were visiting and it was a lovely home ro get ready in and relax before the big i dos! It was also very comfortable for our infant! It was our first time traveling with him and the house was so perfect for our little family. I cannot wait to return! "
1 Block To St. Helena Main Street Shops-Restaurants! Avail Mar 31-April 10&19-29

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

10.0 out of 10, Exceptional, (95)
"Truly a 5 Star stay at Hacienda Sonoma. My wife and I were joined by two other wonderful couples and this was their first visit to Wine Country. Having Hacienda as our base made this trip even better than expected. Bridgett was such an excellent host and provider great communication and advice! I can't imagine staying anywhere else when we plan our next visit to Napa/Sonoma! Thanks Bridgett!!! Tim & Elle"
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, (58)
"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

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

9.6 out of 10, Exceptional, (29)
"Wonderful stay at the Cozy Woodland Estate. Idyllic surroundings with babbling creek that brings all the sounds of nature around you. Just what our party of 3 needed for a cozy, easy retreat. Thank you so much!"
Cozy Woodland Escape, Hot Tub, Redwood + Water Views, mins from spas in Napa

The Sonoma Valley Cottage

9.8 out of 10, Exceptional, (9)
"This was the perfect location and a beautiful space for our family reunion. The sweetest touch was a high chair for my neice, along with bathroom amenities.Highly recommend!! "
The Sonoma Valley Cottage

Wine Country Get Away

10.0 out of 10, Exceptional, (25)
"Overall stay was good and the location is great for visits to Wine Country. Host was accessible and helpful. "
The price is AED 621
AED 1,622 total
includes taxes & fees
29 Mar - 30 Mar
Wine Country Get Away

Cobb Mountain Chalet Main For

9.6 out of 10, Exceptional, (12)
"A very quiet and comfortable place in a beautiful area. "
The price is AED 338
AED 668 total
includes taxes & fees
31 Mar - 1 Apr
Cobb Mountain Chalet Main For

Tropical Lakefront Retreat with Private Dock & Kayaks

9.8 out of 10, Exceptional, (72)
"We had the best weekend having a birthday celebration! We spent most of the time at the house on the water! We fished from the dock every night and caught a couple of catfish! We had dinners out on the patio and used the gas fire pit! We played lots of pool! We paddle boarded! This VRBO has it all! It was clean, had all the kitchen essentials! We absolutely loved this place and are already planning our next trip! The host was amazing! 10/10 recommend! "
Tropical Lakefront Retreat with Private Dock & Kayaks

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

9.8 out of 10, Exceptional, (23)
"The house is exactly as described! It has everything you need whether you plan to take advantage of the amenities of the property or touring the surrounding wine country, or alittle of both. Joe was a great host, available and responsive to a few questions that we had. The house has a keurig and basic spices like salt/pepper and brita water jugs in the fridge. I would stay here again for sure next time I am in Sonoma. "
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, (12)
"This was hands down the best VRBO we’ve ever stayed in. The home is spectacular, with so many amenities (pool, hot tub, basketball half court) making it great for families. The host (Carl) was so helpful and accommodating. Clearly there was a lot of attention to detail when thinking of how to make guests comfortable in this home. The location is perfect for touring wine country. The bedrooms are large, each with a bathroom and the beds were super comfortable. We didn’t do any cooking but if you...
The price is AED 2,388
AED 3,710 total
includes taxes & fees
30 Mar - 31 Mar
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, (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 AED 492
AED 1,338 total
includes taxes & fees
30 Mar - 31 Mar
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, (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 AED 713
AED 795 total
includes taxes & fees
29 Mar - 30 Mar
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 AED 475
AED 529 total
includes taxes & fees
6 Apr - 7 Apr
Clear Lake Cottages & Marina

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
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.