Middletown Vacations

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

Find the Best Middletown Vacation Packages

Middletown Hotel Deals

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
The price is ￥19,077 per night from Jun 29 to Jun 30
￥19,077
￥28,701 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Had everything I needed a wonderful pool and workout out area was great with group classes. The nightlife at the hotel is nice I went to the country line dancing and it was a lot of fun."

Reviewed on Jun 19, 2025

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
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 ￥19,575 per night from Jun 26 to Jun 27
￥19,575
￥28,642 total
Jun 26 - Jun 27
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"The new rooms in the west wing are nicely laid out and comfortable. The location is very convenient to downtown and 101. The restaurant offers a nice breakfast buffet for $20 or ala carte menu. We had some AC noise - room 288 at the end of the courtyard right next to the roof equipt. Other than that ..."

Reviewed on Jun 16, 2025

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 ￥15,515 per night from Jul 6 to Jul 7
￥15,515
￥17,688 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Off the main road. Property and rooms are nice. Depending on your room, you might get some road noise. Given the price I’d stay here again"

Reviewed on Jun 15, 2025

Holiday Inn Windsor Wine Country by IHG
See all 1,442 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.

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.