Middletown Vacations from $518

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Your Middletown Vacation

Experience the excitement and energy of Middletown with a tailor-made Middletown vacation package. From its rich history to its welcoming locals, you'll never have a boring moment in this city. If your trip to Middletown includes some sightseeing, drop by renowned attractions like Twin Pine Casino, Beaver Creek Vineyards and Langtry Estate and Vineyards. Check out Expedia's extensive range of travel options and start organizing your ultimate vacation to Middletown now.

The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
Dennen's Victorian Farmhouse
Cottages at Little River Cove
Super 8 by Wyndham Fort Bragg
The Weller House
The Inn at Schoolhouse Creek
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Discover the most popular places to visit in Middletown

Middletown Hotel Deals

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
2.5 out of 5
8865 Conde Lane, Windsor, CA
Fully refundable
$127 nightly
The price is $145 total per night from Aug 3 to Aug 4
$145 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (1,025 reviews)
"Nice room and stay"

Reviewed on Jul 6, 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
4 out of 5
2777 4th St, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $207 total per night from Jul 14 to Jul 15
$207 total
Jul 14 - Jul 15
Total includes taxes and fees
8.2/10 Very Good! (1,010 reviews)
"Great place for families. The pool and hot tub are great!"

Reviewed on Jul 5, 2025

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
Hotel La Rose
Hotel La Rose
3.5 out of 5
308 Wilson Street, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $135 total per night from Jul 14 to Jul 15
$135 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (1,181 reviews)
"Historical setting, very well refurbished, excellent location 2 blocks off freeway, great amenities"

Reviewed on Jul 5, 2025

Hotel La Rose
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.

Find the Best Middletown Vacation Packages

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
1,300
Max Temp Winter
55ºF
Max Temp Summer
90ºF
Top Sights
Anderson Marsh State Historic Park, Langtry Estate and Vineyards and Beaver Creek Vineyards

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Frequently asked questions

How much does a Middletown vacation package cost?
Offering great value package deals from $518 on Expedia, you'll be pleasantly surprised at how much a vacation to Middletown costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middletown?
November, December and January are great times to look for cheap Middletown vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Middletown?
You can easily visit all the main attractions in Middletown within a few days, including the popular Twin Pine Casino. If you're looking for an extended Middletown vacation, look at what kind of activities and excursions are available nearby.
How to find the best Middletown package deals?
Use Expedia's handy filters to help you find some fabulous Middletown package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Middletown package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Middletown getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Middletown?
If you're planning an impromptu Middletown trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Middletown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.