Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 Highland Vacation

Book a customized Highland vacation package that includes everything you need and no unnecessary extras. Great for nature, hiking and cycling, consider basing yourself in the neighborhood of Redland. During your trip to Highland, take all the time you need for sightseeing. A great place to start is African Art Museum of Maryland. Stop daydreaming and start traveling. Explore the wide range of options on Expedia today and finally put your Highland vacation plans into motion!

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lyle Washington D.C.

Lyle Washington D.C.

Northwest
CA $653
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,658 reviews)
Amazing stay - I would stay here anytime

Reviewed on Aug 29, 2026

Hotel Burg

Hotel Burg

Leesburg's Old and Historic District
CA $1,288
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (112 reviews)
Great property and the staff is fantastic.!!

Reviewed on Aug 30, 2026

Pendry Baltimore

Pendry Baltimore

Fells Point
CA $1,619
per person
Oct 14 - Oct 17
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,008 reviews)
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

Northwest
CA $972
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
8.8/10 Excellent! (1,016 reviews)
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.
CA $687
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,253 reviews)
Beautiful hotel. Great location.

Reviewed on Aug 30, 2026

Ready to book your vacation to Highland?

Choose your dates

Highland Hotel Deals

Washington Plaza Hotel

Washington Plaza Hotel

10 Thomas Circle NW Washington DC
Fully refundableReserve now, pay when you stay
CA $152
CA $176 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (5,388 reviews)
"I love it clean pretty pool was nice also"

Reviewed on Aug 30, 2026

Washington Plaza Hotel
State Plaza Hotel

State Plaza Hotel

2116 E Street NW Washington DC
Fully refundableReserve now, pay when you stay
CA $165
CA $192 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (2,970 reviews)
"Another great stay at the State Plaza Hotel in foggy bottom , it has become our home and from home when visiting my son who goes to GWU . Everyone friendly , rooms clean , love the dress area off the bathroom and the spotless kitchens . We will be back - 3 1/2 years to go :)))"

Reviewed on Aug 30, 2026

State Plaza Hotel
Arlo Washington DC

Arlo Washington DC

333 G St NW Washington DC
Fully refundableReserve now, pay when you stay
CA $158
CA $241 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (1,992 reviews)
"Door to bathroom did not shut. Key to room stopped working and staff were unhelpful and unapologetic. Service was mediocre. Would not return."

Reviewed on Aug 30, 2026

Arlo Washington DC
See all 4,259 properties in Highland
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 Highland vacation package cost?
You can pick up a vacation package to this top destination from CA $653 on Expedia. However, how much your vacation to Highland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Highland?
January, February and April are the best times to search for cheap Highland vacation packages. Travelling in less busy months means you can usually find better prices on accommodations and flights.
How many days is enough for Highland?
Generally, a handful of days is enough to go to the top attractions during your Highland vacation. But if you want to have some time to relax or take day tours, think about extending your trip.
How to find the best Highland package deals?
Bagging a cheap Highland package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Highland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can customize your Highland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Highland?
If you've got your Highland vacation dates finalized, book as early as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Highland?
  1. Choose your dates: The things you want to do in Highland and your favourite season can help you decide when to go.
  2. Set your budget: Factor in expenses such as flights, transportation and food when calculating how much to put aside for your trip to Highland. Then, pick a property that suits your budget, whether that's an economical option or a swankier retreat.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to experience in Highland. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Highland vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.