Middletown Trips (flight + hotel)

Photo by Matthew Walls

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Top hotels in Middletown

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 P6,136 per night from Aug 17 to Aug 18
P6,136
P6,995 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"It was a great stay overall."

Reviewed on Jul 29, 2025

Holiday Inn Windsor Wine Country by IHG
Hotel La Rose

Hotel La Rose

3.5 out of 5
308 Wilson Street, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,212 reviews)
comfy and fine
"windows that open made it ideal for me. i can't take feeling sealed inside a temperature controlled room. i also appreciated the history and charm. better internet would go a long way."

Reviewed on Jul 28, 2025

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Hotel La Rose
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
The price is P6,853 per night from Aug 3 to Aug 4
P6,853
P7,812 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
"Vehicle was gated in and safe."

Reviewed on Jul 29, 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
See all 1,443 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.

Popular places to visit

Rabbit Hill Preserve

You can take time to visit Rabbit Hill Preserve during your travels to Middletown. Make time to visit the spas and casinos while you're in the area.

Rabbit Hill Preserve

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.