Middletown Holidays

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Photo by Matthew Walls

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Middletown Holiday

Our pick of the best 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 NZ$318 per night from 1 Sept to 2 Sept
NZ$318
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (1,011 reviews)
"Solid hotel with the quintessential/classic Hyatt Regency feel you’d expect. Friendly staff, clean facilities and rooms, and a great location. The only demerit I have is the noise. Its proximity to the freeway means you hear traffic when lounging around the pool or if your windows are open (but rooms ..."

Reviewed on 13 Aug. 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 NZ$206 per night from 24 Aug to 25 Aug
NZ$206
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Stayed for one night and everyone was super helpful. Clean room as well. If ever needed to in the area I will return"

Reviewed on 12 Aug. 2025

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 NZ$207 per night from 15 Sept to 16 Sept
NZ$207
15 Sept - 16 Sept
includes taxes & fees
8.2/10 Very Good! (1,973 reviews)
"I really like The Sandman as it was easy to get to, check in was fast and the room was very nice and comfortable. The breakfast the next morning was very nice. The onlybdownside was that there was not enough seating. It was a little chilly to dit at the pool tables. Other than that, it was ..."

Reviewed on 12 Aug. 2025

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection
See all 1,464 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 holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages. Bear in mind that school holiday 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 holiday, 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 holiday package as soon as possible.
Is it cheaper to book a Middletown holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging accommodation and flights individually. Better still, you can customise 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 holiday 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 favourite 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 holiday package.

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