Middletown Vacation Packages

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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.

Top Middletown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Dennen's Victorian Farmhouse
Cottages at Little River Cove
SCP Mendocino Coast Lodge
The Inn at Schoolhouse Creek
Agate Cove Inn

Ready to book your vacation to Middletown?

 

Choose your dates

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 CA $176 per night from Sep 1 to Sep 2
CA $176
CA $260 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Jonathan, the bartender was an amazing guy. He put an ear out there so I could talk. We had a great conversation."

Reviewed on Aug. 22, 2025

Hyatt Regency Sonoma Wine Country
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 CA $146 per night from Sep 15 to Sep 16
CA $146
CA $169 total
Sep 15 - Sep 16
includes taxes & fees
8.2/10 Very Good! (1,967 reviews)
Front Desk Was Very Accomodating
"Arrived late evening. The front desk was very professional and accommodating. Room was clean and spacious. The room had a hot pot and microwaves."

Reviewed on Aug. 22, 2025

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection
Hotel La Rose

Hotel La Rose

3.5 out of 5
308 Wilson Street, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 28 to Aug 29
CA $140
CA $162 total
Aug 28 - Aug 29
includes taxes & fees
9/10 Wonderful! (1,231 reviews)
"Great!"

Reviewed on Aug. 23, 2025

Hotel La Rose
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

Frequently asked questions

How much does a Middletown vacation package cost?
You can pick up a vacation package to this popular destination from CA $542 on Expedia. However, how much your vacation to Middletown costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Middletown?
Plan your trip for the off-peak season and you're likely to score cheap Middletown vacation packages. Bear in mind that public holidays and major local events can have an impact on prices, so do your research before booking.
How many days is enough for Middletown?
You can visit all the major sights in Middletown within a few days, including the popular Langtry Estate and Vineyards. If you're looking for a longer Middletown vacation, check out which kind of activities and excursions are available in the area.
How to find the best Middletown package deals?
Bagging a cheap Middletown package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Middletown package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Middletown vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Middletown?
If you're planning a spur-of-the-moment Middletown vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Middletown?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Middletown.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Middletown. Then, choose a property that suits your budget, whether that's a wallet-friendly stay or a more upscale getaway.
  3. Decide how long to go away for: Now that you're up to speed on Middletown, you can figure out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Middletown vacation package that brings all your bookings together.

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