Book Holiday Homes in Middletown
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Featured Holiday Homes in Middletown

Wine Country Harvest Vacation Home

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

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

Cozy Cottage: Panoramic Lake Views, WiFi, Deck

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

1 Block To St. Helena Main Street Shops-Restaurants! Avail Jan 20-Feb 2, 10-16

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
Middletown Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middletown vacation homes are the perfect way for you to wing it.
Holiday houses in Middletown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middletown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middletown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middletown with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middletown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Middletown Holiday Homes essential information
Accommodation | 652 Holiday Homes |
---|---|
Lowest Price | NZ$152 |
Highest Price | NZ$302 |
Popular accommodation | Wine Country Harvest Vacation Home, Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N, Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi, Cozy Cottage: Panoramic Lake Views, WiFi, Deck, 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, 1 Block To St. Helena Main Street Shops-Restaurants! Avail Jan 20-Feb 2, 10-16, 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 |
More accommodations in Middletown
Top trending hotels in Middletown

The Sandman, Ascend Hotel Collection

Holiday Inn Windsor Wine Country by IHG

Flamingo Resort & Spa

Hyatt Regency Sonoma Wine Country
More ways to explore Middletown
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^Subject to availability and chosen travel dates.