Deals on vacations and trips to Middletown

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Middletown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Save 100% on your flight
Price was $826, price is now $566 per person
$566
per person
Sep 18 - Sep 22
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
The Westin Annapolis

The Westin Annapolis

4 out of 5
Save 100% on your flight
Price was $1,071, price is now $677 per person
$677
per person
Sep 18 - Sep 22
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and snack bar/deli.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $1,001, price is now $634 per person
$634
per person
Sep 18 - Sep 22
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,865, price is now $1,188 per person
$1,188
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.
Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
Price was $2,985, price is now $2,038 per person
$2,038
per person
Sep 21 - Sep 26
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Top Middletown hotels deals

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
Free Cancellation
$101 nightly
The price is $113 total per night
$113 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr Frederick MD
Free Cancellation
$85 nightly
The price is $94 total per night
$94 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Best Western Historic Frederick

Best Western Historic Frederick

2.5 out of 5
420 Prospect Blvd Frederick MD
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $87 total per night
$87 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, luggage storage, and laundry facilities are also on offer.
Pool
Breakfast included
SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

2.5 out of 5
111 Byte Drive Frederick MD
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $129 total per night
$129 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features an indoor pool and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hotel Burg

Hotel Burg

4 out of 5
208 S King Street Leesburg VA
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $251 total per night
$251 total
Aug 9 - Aug 10
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.
Spa
Pet friendly
The Plaza Inn & Suites

The Plaza Inn & Suites

2.5 out of 5
931 Dual Highway, Building A Hagerstown MD
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $78 total per night
$78 total
Jul 10 - Jul 11
Total with taxes and fees
An indoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Pet friendly
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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.

Stay near popular Middletown attractions

Maryland National Golf Club

Enjoy a round of golf in Middletown at Maryland National Golf Club. Discover the coffeehouses and its festivals while you're in the area.
See properties

Frequently asked questions

How much are vacation packages to Middletown?
Get ready to be surprised — you can find yourself in Middletown for as little as $566. Here at Travelocity, we save you time and money with our excellent vacation packages. With flights, hotels and tours all available at our one-stop shop, why wait?
How long should my Middletown vacation be?
The majority of people book their hotel for 3 nights in Middletown. But that doesn't necessarily mean you have to do the same. How long you decide to stay boils down to what you want to do during your vacation. If you intend to discover every nook and cranny of this incredible place, treat yourself to another night or two (or even an extra week!).
Where can I get the best vacation package deals for Middletown?
No matter your style, Travelocity can help you score a great Middletown package deal. All you need to do is pick and choose between our 400 partner airlines and 1,000,000 properties across the globe.
Why should I purchase my Middletown vacation bundle via Travelocity?
We make traveling the world easy. Whether you're looking for a new destination to roam around or want to ensure you get the best deal around, we're here to help. Our 24/7 customer care, excellent service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I save money on my Middletown car rental if I book it with hotels and flights?
Combining your flight, hotel and car into a Middletown vacation package is a great way to land the best prices. Plus, having your own car rental gives you total freedom to find your way to all those amazing sights you'd like to explore. Sitting 45 mi away from Middletown, White House is one place that should be on your must-do list. Load up the car and make a day trip of it.
Which airport is best for Middletown?
For many visitors, a trip to Middletown means passing through Ronald Reagan Washington National Airport (DCA). This popular airport is located 50 mi southeast of the downtown area. You could also choose to jet into Washington Dulles Intl. Airport (IAD) (35 mi away from central Middletown) or Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (50 mi away from central Middletown).
What is there to do in Middletown?
You'll feel a particular magic in the air as you stroll the streets of Middletown. Maryland National Golf Club and Orchid Cellar Winery are just a couple of attractions that make this city so special, so put them at the top of your to-do list.
Where should I stay when visiting Middletown?
Many travelers opt to stay at the Beautiful historical town, 3 bedrooms, countryside. It's sure to be a good base for your Middletown getaway.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

A stone tower with a staircase leading up to it.
A stone archway with inscriptions and statues, surrounded by grass and trees.
A stone tower with a flagpole, surrounded by trees and a cloudy sky.
A stone tower with a flagpole and an American flag.