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Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guesthouse in Middletown
Love Shack, right in Middletown!
Come stay in the good vibes of the Love Shack. Built for one of my sons and his sweet love to escape his mother's hearing range.... It was built to be inviting to snuggle up in and enjoy. The cottage is comfortable and charming with a newly added bathroom and kitchen area. The back deck faces the morning sun, and my goat around the corner who loves it if you bring her your old carrots and apples. Walking distance to shops and restaurants in Middletown. All folks, races, LGBT friendly.
$105 per night
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Home in Middletown
Emerald Lodge
I just updated what was the "Locust Lodge" to the "Emerald Lodge"! Now let's see if this name sticks or I change it to "Lime and Tequila Lodge", and.. still.. open to suggestions. I decided to paint one of the walls green, and upgraded a few other things that I am sure you will appreciate. There is a new memory foam mattress, flat screen TV, desk, table with four chairs, all sorts of new kitchen accoutraments, a gorgeous water color painting from a friend of mine, and lots of love.
$122 per night
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Private room in Middletown
NEW !! Suite and Dog-Yard in Creekside Cabin
Annie's Creekside Cabin in Anderson Springs is back! You may remember my vacation rental, friendly to pets, that burned down in 2015. Well, I'm back with a dog-friendly suite suitable for social distancing. It's got its own deck and entrance, private bathroom, fridge and microwave, with air-conditioning, and removable doggie door into fenced yard. You can wade in the creek with your pooch or leave him while you travel minutes away to Harbin, casino, and wineries.
$75 per night
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Stay near Middletown's top sights

Photo of Cowpoke Cafe
Cowpoke Cafe14 locals recommend
Photo of La Parrilla Mexican Grill
La Parrilla Mexican Grill15 locals recommend
Photo of Buddha Thai Kitchen
Buddha Thai Kitchen23 locals recommend
Photo of Rosales Market
Rosales Market6 locals recommend
Photo of Mount St Helena Brewing Company
Mount St Helena Brewing Company6 locals recommend
Photo of Su Garden Restaurant
Su Garden Restaurant4 locals recommend

Other great vacation rentals in Middletown

Guesthouse in Middletown
The Well House
$106 per night
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Cabin in Cobb
The Cobb Haus
$166 per night
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Private room in Cobb
Separate Guest Suite in Cobb Mountain Home
$75 per night
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Cabin in Middletown
Cozy PET-FRIENDLY 1 bd cabin w/ indoor fireplace
$121 per night
Cabin in Cobb
Emerald Cabin in Whispering Pines on Cobb Mountain
$121 per night
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Cottage in Middletown
Adorable Cottage - Walking distance to downtown
$106 per night
Cabin in Cobb
Cobb MTN Hideaway - A retreat away from it all
$195 per night
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Cabin in Cobb
Cozy Cabin in Cobb Mtn near Harbin Hot Springs
$163 per night
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Home in Middletown
Ranch near Harbin and Langtry Winery
$166 per night
Guest suite in Hidden Valley Lake
Sunset Cottage Relax and Enjoy.
$184 per night
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Guesthouse in Middletown
Modern studio in a vineyard
$215 per night
Home in Middletown
Middletown home with hot tub and huge deck!
$232 per night
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