Middletown Holidays from £1,198

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Your Middletown Holiday

Experience the excitement and energy of Middletown with a tailor-made Middletown holiday 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 organising your ultimate holiday to Middletown now.

The Latest Middletown Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Brewery Gulch Inn

Brewery Gulch Inn

4 out of 5
per person
11 Sept - 15 Sept
found 1 day ago
Return direct flight included
London (LON) to Santa Rosa (STS)
9.8/10 Exceptional! (109 reviews)
Total gem! The place feels like a second home when mom cooks you your favorite meal. Stayed twice now and know we will be back.

Reviewed on 1 Jun 2025

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
1,300
Max Temp Winter
13ºC
Max Temp Summer
32ºC
Top Sights
Anderson Marsh State Historic Park, Langtry Estate and Vineyards and Beaver Creek Vineyards

Our pick of the best Middletown Hotel Deals

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
Stay at this golf hotel in Windsor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,005 reviews)
"Breakfast was good and bed was ok, but odd that we couldn't exit and enter the building via the stairwell, only the elevator which took a while. very nice staff. Also bummer that the hot tub and pool were out of order for the first few days we were there. convenient to wineries though."

Reviewed on 24 Jun 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
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
Stay at this 4-star spa hotel in Santa Rosa. Enjoy free Wi-Fi, 2 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
8.2/10 Very Good! (1,001 reviews)
"4 stars for the specific categories you asked about, but 5 stars overall because we just really enjoyed being there. Not perfect but so much fun! In particular, re table service in the restaurant, the individual servers were great but the system needs to be improved. We didn't know if we were supposed ..."

Reviewed on 24 Jun 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
Stay at this 4-star hotel in Santa Rosa. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,005 reviews)
"Overall a good choice and well located for our visit to Wineries in Sonoma and the Russian River Valley. Walking distance to a lot of great restaurants in downtown Santa Rosa."

Reviewed on 24 Jun 2025

Hyatt Regency Sonoma Wine Country
See all 1,444 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Middletown travel package cost?
From as low as £1,198. Yes, you read that correctly. Our Middletown travel packages are the easiest way to make your budget go further. Bundle your favourite hotels, flights and car rentals and discover this lively destination.
If I'm not able to travel, can I cancel my Middletown travel package?
Whether it's your hotel or flight, yes, you can amend or cancel it. Locked in your Middletown travel package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may be charged a fee by your airline, hotel or car rental company. For more details, head to our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Middletown?
Bundle your hotels and flights with Expedia to save on your next big adventure. With more than 550 partner airlines and 1,000,000 hotel options worldwide, your Middletown travel package can be tailored exactly to suit your budget. With all that extra cash, why not throw in some exciting tours and experiences? It's an easy way to unlock even more bargains. Your dream holiday in Middletown is much closer than you thought!
Does Expedia offer Book Now, Pay Later Middletown holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Take a look at these flexible payment options:
  • Pay monthly holidays: Klarna has manageable monthly payment plans that suit all budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Middletown?
A holiday in Middletown isn't complete without stopping by Twin Pine Casino, Langtry Estate and Vineyards and Beaver Creek Vineyards. Stay close to these popular sights and make sightseeing easy.
What are the top hotels in Middletown?
Best Western El Grande Inn and Travelodge by Wyndham Clearlake are two of the most popular properties in Middletown. Why not take a look at the facilities and amenities at each and then decide?
How far in advance should I book my Middletown holiday?
To bag discount prices, book as soon as you can. Airlines usually start selling tickets, along with some of the lowest fares, nearly a year in advance. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to Middletown, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Middletown travel package include?
It all comes down to what sort of getaway you're planning. Middletown holiday deals can include flights, hotels and car rentals. You can mix and match to find the travel package that suits your style and budget. You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Middletown travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a neat package. But your options don't end at hotels. Expedia features all kinds of properties, including holiday rentals like mountain cabins and city apartments. The list goes on!
Can I choose my airline with a Middletown Expedia travel package?
With a travel package, you're in charge. Whether you'd prefer to fly to Middletown in coach or business class, simply select from the available airline options. Expedia has access to over 550 partner airlines globally.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.