Middletown Vacations

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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.

Discover the most popular places to visit in Middletown

Bio wine in Lake County

Beaver Creek Vineyards

You can enjoy a tasting or tour at Beaver Creek Vineyards during your travels to Middletown. Check out the spas and wineries in this relaxing area.

Beaver Creek Vineyards

Twin Pine Casino

Why not try your luck with a visit to Twin Pine Casino during your time in Middletown? Check out the spas and wineries in this walkable area.

Twin Pine Casino

Langtry Estate and Vineyards

You can enjoy a tasting or tour at Langtry Estate and Vineyards during your travels to Middletown. Check out the spas and wineries in this romantic area.

Langtry Estate and Vineyards

Middletown Hotel Deals

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $106 total per night from Nov 3 to Nov 4
$106 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (2,019 reviews)
"This has been my go to place to stay in Santa Rosa whenever I need to spend the night for usually medical purposes."

Reviewed on Oct 18, 2025

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
755 Silverado Trl, Calistoga, CA
Fully refundableReserve now, pay when you stay
$748 nightly
The price is $860 total per night from Nov 19 to Nov 20
$860 total
Nov 19 - Nov 20
Total with taxes and fees
9.4/10 Exceptional! (674 reviews)
"Gorgeous resort, great food"

Reviewed on Sep 26, 2025

Solage, Auberge Collection
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
$162 nightly
The price is $188 total per night from Nov 16 to Nov 17
$188 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
"The staff was very nice and quick to respond to a couple of requests I had. Thank you for making the ur stay pleasant"

Reviewed on Oct 17, 2025

Hyatt Regency Sonoma Wine Country
See all 1,477 properties in Middletown
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 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 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.