Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Wine Country Harvest Vacation Home

Wine Country Harvest Vacation Home

Santa Rosa
Stay at this vacation home in Santa Rosa. Enjoy concierge services, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Spring Lake Park ...
Wine Country Harvest Vacation Home
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

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

Kenwood
Book a stay at this family-friendly vacation home in Kenwood. Enjoy free WiFi, private pools, and a water park. Popular attractions VJB Vineyard & Cellars and ...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

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

Healdsburg
Stay at this vacation home in Healdsburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Russian River and Windsor Oaks Vineyards ...
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
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Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Clearlake Oaks
Stay at this vacation home in Clearlake Oaks. Enjoy air conditioning. Popular attractions Clearlake Oaks Boat Launch and Shannon Ridge Vineyards and Winery are ...
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

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

Kenwood
Stay at this vacation home in Kenwood. Enjoy free WiFi, a garden, and patios. Popular attractions Chateau St. Jean Winery and Ledson Winery and Vineyards are ...
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

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

St Helena
Stay at this vacation home in St. Helena. Enjoy free WiFi, private pools, and patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
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

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

Saint Helena
Stay at this vacation home in St. Helena. Enjoy a fitness center, a garden, and patios. Popular attractions Castello di Amorosa and Merryvale Vineyards are located ...
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.

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

Kenwood
Book a stay at this family-friendly vacation home in Kenwood. Enjoy free WiFi, a water park, and a garden. Popular attractions Chateau St. Jean Winery and Ledson ...
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

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

Kelseyville
Book a stay at this beach vacation home in Kelseyville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Clear Lake State Park and Mount Konocti ...
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
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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.

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

Top trending hotels in Middletown

The Sandman, Ascend Hotel Collection

The Sandman, Ascend Hotel Collection

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is NZ$152 per night from 20 Apr to 21 Apr
NZ$152
includes taxes & fees
20 Apr - 21 Apr
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, Ascend Hotel Collection
Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is NZ$211 per night from 20 Apr to 21 Apr
NZ$211
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Windsor Wine Country by IHG
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$302 per night from 27 Apr to 28 Apr
NZ$302
includes taxes & fees
27 Apr - 28 Apr
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$227 per night from 14 Apr to 15 Apr
NZ$227
includes taxes & fees
14 Apr - 15 Apr
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
Don't see what you're looking for?
See all available properties in Middletown
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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.