Book Holiday Homes in Middletown

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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
Holiday Homes
Lowest Price
NZ$164
Highest Price
NZ$1,425
Popular accommodation
The Sandman Hotel , Solage, Auberge Resorts Collection, Flamingo Resort & Spa, Hyatt Regency Sonoma Wine Country

Top trending hotels in Middletown

The Sandman Hotel

The Sandman Hotel

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is NZ$164 per night from 5 Feb to 6 Feb
NZ$164
includes taxes & fees
5 Feb - 6 Feb
Stay at this 3-star business-friendly hotel in Santa Rosa. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the bar in our ...
The Sandman Hotel
Solage, Auberge Resorts Collection

Solage, Auberge Resorts Collection

5 out of 5
755 Silverado Trl, Calistoga, CA
Fully refundableReserve now, pay when you stay
The price is NZ$1,425 per night from 13 Feb to 14 Feb
NZ$1,425
includes taxes & fees
13 Feb - 14 Feb
Stay at this 5-star luxury hotel in Calistoga. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Solage, Auberge Resorts Collection
Flamingo Resort & Spa

Flamingo Resort & Spa

4 out of 5
2777 4th St, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is NZ$309 per night from 31 Jan to 1 Feb
NZ$309
includes taxes & fees
31 Jan - 1 Feb
Stay at this 4-star spa hotel in Santa Rosa. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Flamingo Resort & Spa
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Hyatt Regency Sonoma Wine Country

Hyatt Regency Sonoma Wine Country

4 out of 5
170 Railroad Street, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is NZ$349 per night from 5 Feb to 6 Feb
NZ$349
includes taxes & fees
5 Feb - 6 Feb
Stay at this 4-star hotel in Santa Rosa. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in ...
Hyatt Regency Sonoma Wine Country
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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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^Subject to availability and chosen travel dates.