Upper Hooper Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Ready to book your vacation to Upper Hooper Island?

 

Choose your dates

Upper Hooper Island Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Mar 29 to Mar 30
CA $252
CA $351 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
The pools were warm and relaxing

Reviewed on Mar 9, 2026

Hyatt Regency Chesapeake Bay
Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

2.5 out of 5
21885 Three Notch Rd Lexington Park MD
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Apr 6 to Apr 7
CA $133
CA $148 total
Apr 6 - Apr 7
includes taxes & fees
8.6/10 Excellent! (675 reviews)
There was a terrible cigarette smell. We ended having to leave in middle of night because we could no longer stand it.

Reviewed on Mar 2, 2026

Comfort Inn & Suites Lexington Park near Pax River
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Mar 15 to Mar 16
CA $97
CA $107 total
Mar 15 - Mar 16
includes taxes & fees
6.6/10 (1,004 reviews)
It was short and the bathroom could have been a bit cleaner.

Reviewed on Mar 2, 2026

Days Inn & Suites by Wyndham Cambridge
See all 333 properties in Upper Hooper Island
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

Can I cancel my flight booking to Upper Hooper Island due to COVID-19?
In response to these difficult times, many airlines are offering greater flexibility. Visit our Customer Service Portal for details about canceling or changing your booking due to COVID-19.
What's the best way to find cheap flights to Upper Hooper Island that have flexible change policies?
By using our smart "No change fee" filter, that's how. Simply enter your travel details, click "Search," then check the box underneath the "Flexible change policies" subheading (left-hand side of your screen). Expedia makes it easy to find affordable, flexible tickets to Upper Hooper Island.
What are some of the general tips for travelers to Upper Hooper Island during the COVID-19 outbreak?
If it's your first time traveling during the COVID-19 pandemic, you'll notice plenty of new rules and standards in place. Take note of these tips and make your trip to Upper Hooper Island go off without a hitch:
  • Find out if any travel restrictions apply to your destination and origin before locking in a flight. Also check if there are any special conditions you'll need to follow on arrival, such as taking a COVID-19 test.
  • You must wear a face mask at the airport, including at security checkpoints. Be prepared to lower your mask for ID verification when asked by a TSA officer.
  • To reduce the likelihood of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to take it out of your bag for scanning.
  • Put any personal items (e.g, keys, phone and coins) in your carry-on rather than a bin to minimize handling during screening.
  • Separate any food you have for screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Upper Hooper Island?
There are a couple of carriers that'll fly you to or near Upper Hooper Island. Here are your options:
  • American Airlines - 5534 flights to or near Upper Hooper Island each month, including 5326 flights to Ronald Reagan Washington National Airport (DCA) and 208 flights to Washington Dulles Intl. Airport (IAD) per month.
  • Delta - 1341 flights to or near Upper Hooper Island each month, including 859 flights to Ronald Reagan Washington National Airport (DCA) and 481 flights to Washington Dulles Intl. Airport (IAD) per month.

How can I find cheap tickets to Upper Hooper Island?
One of the easiest ways to bag cheap tickets to Upper Hooper Island is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Upper Hooper Island in the last seven days was . Booking well in advance will generally help you score an even better deal.
How much is a flight to Upper Hooper Island?
The price of a round-trip airfare to Upper Hooper Island in the last seven days ranged between and . If you were traveling one way out of (), you could have gotten a fare from only .
What are the most popular airports to fly into in Upper Hooper Island?
Adventure awaits the moment you arrive at one of these well-known Upper Hooper Island airports:
  • Washington Dulles Intl. Airport (IAD) - 9558 flights per month.
  • Ronald Reagan Washington National Airport (DCA) - 7771 flights per month.

When is the cheapest time to fly to Upper Hooper Island?
If you can be flexible with what day you jet off to Upper Hooper Island, try to fly out earlier in the week. The most economical day to take off is generally Tuesday, followed closely by Monday. Saturday is typically the priciest day, with a lot of people preferring to fly on weekends.
How much is a plane ticket to Upper Hooper Island?
In the last seven days, plane tickets to Upper Hooper Island fluctuated from to .
Which airlines with flights to Upper Hooper Island employ COVID-19 cleanliness policies?
While traveling during a pandemic can be nerve-wracking, airlines are doing their bit to ensure the well-being of passengers and crew. Here are a few carriers that have implemented changes:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

Explore a world of travel with Expedia

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