Middletown Holidays

Photo by Matthew Walls

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Top hotels in Middletown

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 S$243 per night from 10 Aug to 11 Aug
S$243
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (1,027 reviews)
"The hotel was in a great area for walking to shopping and restaurants. Our back patio was very dirty, they did come and clean it when requested. We had issues with our phone and our neighbors had taken our patio furniture, but they were on it and had it fixed right away. I believe we would stay there ..."

Reviewed on 31 Jul, 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 S$157 per night from 10 Aug to 11 Aug
S$157
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Best hotel in Sonoma County"

Reviewed on 1 Aug, 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! (1,207 reviews)
"Convenient.. close to freeway and walkable to restaurants I could not connect to WiFi but front desk gave me a hotspot to use. Rooms are old but spacious and clean"

Reviewed on 2 Aug, 2025

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Hotel La Rose
See all 1,445 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.