Middletown Vacations from $518
Book a Hotel + Flight or Car together to unlock savings
Photo by Matthew Walls
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
The Latest Middletown vacation packages
Price found within the past 48 hours. Click for updated prices.
Cottages at Little River Cove
Save 100% on your flight
per person
Aug 29 - Sep 1
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Santa Rosa (STS)
9.4/10 Exceptional! (23 reviews)
We really enjoyed our stay! The door code didn’t work when we arrived, but the property manager was quick to come help us. The amenities were wonderful as well. The shrubs could be cut back some and the spider webs around the cabins weren’t too appealing to see. Other than that, we loved it!
Reviewed on Jun 23, 2025
Super 8 by Wyndham Fort Bragg
per person
Aug 29 - Sep 1
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Santa Rosa (STS)
7.8/10 Good! (1,006 reviews)
The property is clean and comfortable. Really closed to everything. But I wouldn’t say it has breakfast. I wouldn’t count cereal and toast without butter breakfast. That part is only part that sucked.
Reviewed on Jun 30, 2025
The Weller House
per person
Aug 29 - Sep 1
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Santa Rosa (STS)
9.4/10 Exceptional! (101 reviews)
Unique B&B. The staff was friendly but there was only coffee and cookies for breakfast. The exterior could use some cleaning up. In all, it was more expensive compared to other B&B's while offering less.
Reviewed on Jul 7, 2025
Discover the most popular places to visit in Middletown
Beaver Creek Vineyards
You can enjoy a tasting or tour at Beaver Creek Vineyards during your travels to Middletown. Check out the spas and wineries in this relaxing area.
Twin Pine Casino
4/5(8 reviews)
Why not try your luck with a visit to Twin Pine Casino during your time in Middletown? Check out the spas and wineries in this romantic area.
Langtry Estate and Vineyards
You can enjoy a tasting or tour at Langtry Estate and Vineyards during your travels to Middletown. Check out the spas and wineries in this romantic area.
Middletown Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane, Windsor, CA
Fully refundable
$127 nightly
The price is $145 total per night from Aug 3 to Aug 4
$145 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (1,025 reviews)
"Nice room and stay"
Reviewed on Jul 6, 2025
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton
2777 4th St, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $207 total per night from Jul 14 to Jul 15
$207 total
Jul 14 - Jul 15
Total includes taxes and fees
8.2/10 Very Good! (1,010 reviews)
"Great place for families. The pool and hot tub are great!"
Reviewed on Jul 5, 2025
Hotel La Rose
308 Wilson Street, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $135 total per night from Jul 14 to Jul 15
$135 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (1,181 reviews)
"Historical setting, very well refurbished, excellent location 2 blocks off freeway, great amenities"
Reviewed on Jul 5, 2025
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.
Find the Best Middletown Vacation Packages
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Sonoma County Airport (STS) |
Population | 1,300 |
Max Temp Winter | 55ºF |
Max Temp Summer | 90ºF |
Top Sights | Anderson Marsh State Historic Park, Langtry Estate and Vineyards and Beaver Creek Vineyards |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Hotels near Beaver Creek Vineyards
- Hotels near Twin Pine Casino
- RV Parks in Harbin Springs
- Hidden Valley Lake Hotels
- Cabin Rentals in Hidden Valley Lake
- Cottages in Hidden Valley Lake
- Resorts & Hotels with Spas in Hidden Valley Lake
- Lodges in Hidden Valley Lake
- 5 Star Hotels in Hidden Valley Lake
- Hotels on the Lake in Hidden Valley Lake
- B&B in Hidden Valley Lake
- 4 Star Hotels in Hidden Valley Lake
- Family Hotels in Hidden Valley Lake
- Motels in Hidden Valley Lake
- RV Parks in Hidden Valley Lake
- Hotels near Langtry Estate and Vineyards
- Hotels near Robert Louis Stevenson State Park
- Hotels near Cobb Mountain
- Cobb Hotels
- Cabin Rentals in Cobb
- Cottages in Cobb
- Motels in Cobb
- Resorts in Cobb
- Apartments in Cobb
- Extended Stay Hotels in Cobb
- B&B in Cobb
- 4 Star Hotels in Cobb
- Pet-friendly Hotels in Cobb
- 5 Star Hotels in Cobb
- Loch Lomond Hotels
- Hotels near Chateau Montelena Winery
- Hotels near Storybook Mountain Vineyards
- Hotels near Bennett Lane Winery
- Hotels near Vincent Arroyo Winery
- Hotels near Old Faithful Geyser of California
- Sunrise Vista Hotels
- Lower Lake Hotels
- Hotels near Tamber Bey Vineyards
- Cabin Rentals in Lower Lake
- Motels in Lower Lake
- RV Parks in Lower Lake
- Apartments in Lower Lake
- B&B in Lower Lake
- Romantic Hotels in Lower Lake
- 4 Star Hotels in Lower Lake
- Resorts in Lower Lake
- Cottages in Lower Lake
- Vacation Homes in Lower Lake
- Hotels near Summers Winery
- Calistoga Hotels
- Hotels near Hanna Winery and Vineyards
- Hotels near Vigilance Vineyards & Winery
- Hotels near Oat Hill Mine Trail
- Hotels near Anderson Marsh State Historic Park
- Twin Pine Casino
- Hidden Valley Lake Vacations
- Langtry Estate and Vineyards
- Visit Hidden Valley Lake
- Robert Louis Stevenson State Park
- Cobb Mountain
- Visit Cobb
- Visit Aetna Springs
- Chateau Montelena Winery
- Storybook Mountain Vineyards
- Bennett Lane Winery
- Old Faithful Geyser of California
- Vincent Arroyo Winery
- Tamber Bey Vineyards
- Lower Lake Vacations
- Summers Winery
- Hanna Winery and Vineyards
- Visit Lower Lake
- Vigilance Vineyards & Winery
- Oat Hill Mine Trail
- Calistoga Speedway
- Soda Rock Winery
- Calistoga Hot Springs
- Robert Young Estate Winery
- Calistoga Vacations
- Calistoga Visitors Center
- Pioneer Park
- Car rentals near Harbin Springs
- Car rentals near Hidden Valley Lake
- Car rentals near Whispering Pines
- Car rentals near Forest Lake
- Car rentals near Cobb Mountain
- Car rentals near Cobb
- Car rentals near Hobergs
- Car rentals near Loch Lomond
- Car rentals near Aetna Springs
- Car rentals near Sunrise Vista
- Hertz Rental Cars in Lower Lake
- Car rentals near Lower Lake
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.