Middletown Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Walls

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    Save up to NT$5,067 when you book a flight and hotel together*
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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

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 NT$3,796 per night from Aug 11 to Aug 12
NT$3,796
NT$5,625 total
Aug 11 - Aug 12
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"Beautiful property…pleasant staff, clean, and a great location!"

Reviewed on 2025/8/5

Hyatt Regency Sonoma Wine Country
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 NT$3,074 per night from Aug 25 to Aug 26
NT$3,074
NT$3,504 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Awesome !"

Reviewed on 2025/8/6

Holiday Inn Windsor Wine Country by IHG
The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is NT$3,298 per night from Aug 24 to Aug 25
NT$3,298
NT$3,832 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,987 reviews)
"Very comfortable room. Nice amenities"

Reviewed on 2025/8/7

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection
See all 1,449 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.

Discover the most popular places to visit in Middletown

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 relaxing area.

Langtry Estate and Vineyards

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?
Plan your getaway for the shoulder or low season and you're likely to score cheap Middletown vacation packages. Bear in mind that school vacation periods and major festivals and events can impact prices, so do your research before you go.
How many days is enough for Middletown?
You can explore all the main sights in Middletown within a few days, including the must-see Twin Pine Casino. If you're after a longer Middletown vacation, look at which kind of excursions and activities 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.
How to plan a trip to Middletown?

  1. Pick your travel dates: The things you want to do in Middletown and your favorite season will help you decide when to travel.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Middletown.
  3. Decide how long to go for: Now that you're up to speed on Middletown, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a tailored Middletown vacation package.

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