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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Wine Country Harvest Vacation Home
Outdoor dining

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (73)
"Very private large house and yard perfect!"
Wine Country Harvest Vacation Home
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining

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

10.0 out of 10, Exceptional, (223)
"Our group of 12 had an amazing time here! The property is beautiful and fully equipped with everything you’d need! We’d love to come back during summer to you the pool for sure! "
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
A heated pool

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

10.0 out of 10, Exceptional, (14)
"What a fabulous property! We are pretty well traveled group and as “THE best VRBO we have EVER been at!! The attention to details throughout the house is truly incredible. Just a beautiful home and property to stay at"
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Terrace/patio

Cozy Cottage: Panoramic Lake Views, WiFi, Deck

The price is AED 459
AED 735 total
includes taxes & fees
14 May - 15 May
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Terrace/patio

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

10.0 out of 10, Exceptional, (189)
"The house was charming and cozy. Plenty of room, beds and yet intimate. We loved the location too!"
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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (120)
"This is the perfect location because you are secluded yet a short walk into town"
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
Property grounds

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

10.0 out of 10, Exceptional, (252)
"Instructions prior to check were excellent, lovely property, and would recommend this to friends and family for future stays! "
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.
Terrace/patio

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

10.0 out of 10, Exceptional, (99)
"What an amazing property… it was perfect for our group of two couples… So very clean, and every amenity you ever imagine needing was there for us! So many cozy places to relax, both inside and outside! We will definitely be back! Thank you so much, Bridget, for all of your hard work, and for sharing your beautiful property with us! :-)"
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
Interior

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

10.0 out of 10, Exceptional, (60)
"Nice weekend by the lake Great fishing experience "
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
Terrace/patio

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

9.6 out of 10, Exceptional, (30)
"Nice home to stay for a visit to Napa valley"
Cozy Woodland Escape, Hot Tub, Redwood + Water Views, mins from spas in Napa
Wine Country Get Away
Fridge, microwave, oven, stovetop

Wine Country Get Away

9.8 out of 10, Exceptional, (27)
"Great location especially for proximity to our family. So enjoyed being able to have our family over for dinner. our"
The price is AED 621
AED 1,394 total
includes taxes & fees
11 May - 12 May
Wine Country Get Away
Cobb Mountain Chalet Main For
Exterior

Cobb Mountain Chalet Main For

9.6 out of 10, Exceptional, (14)
"A always a great stay this is my fourth stay."
The price is AED 202
AED 533 total
includes taxes & fees
11 May - 12 May
Cobb Mountain Chalet Main For
Tropical Lakefront Retreat with Private Dock & Kayaks
Terrace/patio

Tropical Lakefront Retreat with Private Dock & Kayaks

9.8 out of 10, Exceptional, (75)
"great place to stay"
Tropical Lakefront Retreat with Private Dock & Kayaks
4BD/4BA Heated Pool+Spa+Sonos+8 beds: 11min Healdsburg & Alexander Valley
Outdoor pool, a heated pool

4BD/4BA Heated Pool+Spa+Sonos+8 beds: 11min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (27)
"We spent Thanksgiving week at the home. Description of property is good. Lots of space for families to gather. Good access to groceries in Santa Rosa , good restaurants and wine tours. Outdoor space is ample "
4BD/4BA Heated Pool+Spa+Sonos+8 beds: 11min Healdsburg & Alexander Valley
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
Exterior

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

9.8 out of 10, Exceptional, (87)
"The home was located in a beautiful area. Lots of great shops and restaurants within walking distance."
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
Interior

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

10.0 out of 10, Exceptional, (100)
"Great home, soft linens, fully appointed kitchen . Quiet neighborhood, we look forward to returning soon !"
St. Helena estate, in heart of the Napa wine country, walk to town, on vineyard
Pool Paradise in Wine Country!
Outdoor pool, a heated pool

Pool Paradise in Wine Country!

3.0 star property
10.0 out of 10, Exceptional, (6)
"This place was very comfortable for 4 adults and a toddler. We enjoyed the hot tub, yard and game room. This place was also well equipped for children with a pack n play, high chair, and toys. Is walkable to the local coffee shop, restaurants and wine tastings rooms as well. Would stay again!"
Pool Paradise in Wine Country!
Wine Country Lux Villa w/ Hot Tub and Pool
Fridge, microwave, oven, stovetop

Wine Country Lux Villa w/ Hot Tub and Pool

10.0 out of 10, Exceptional, (13)
"Carl was super hospitable and we had a great stay. The property was spectacular and everything was as advertised! Would highly recommend and can't wait to come back!"
The price is AED 4,040
AED 5,631 total
includes taxes & fees
15 May - 16 May
Wine Country Lux Villa w/ Hot Tub and Pool
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
Outdoor dining

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

9.6 out of 10, Exceptional, (53)
"So relaxing and peaceful place my family loved it unfortunately was for a short time but next time definitely will stay longer no doubt about booking it again "
The price is AED 547
AED 1,407 total
includes taxes & fees
11 May - 12 May
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
Wine Country Redwood Estate in the Heart of Wine Country
Terrace/patio

Wine Country Redwood Estate in the Heart of Wine Country

9.8 out of 10, Exceptional, (87)
"Truly a beautiful property. "
Wine Country Redwood Estate in the Heart of Wine Country
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
Deep-tissue massages, Swedish massages, prenatal massages, massages

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (45)
"perfect place"
The price is AED 713
AED 795 total
includes taxes & fees
11 May - 12 May
Backyard Garden Oasis
Calistoga Creek Side Mountain Estate
A heated pool

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
View from property

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (306)
"This place was beautiful!"
The price is AED 537
AED 599 total
includes taxes & fees
12 May - 13 May
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.