Highland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Comfort Inn & Suites Baltimore Inner Harbor
Downtown Baltimore
CA $539
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
5.2/10 (1,000 reviews)
Staff was wonderful however the cleanliness wasn’t up to par and the upkeep of the hotel was horrible… we didn’t even shower there was mold all over the shower and shower curtain .. there was coffee splattered on the wall hair in the fridge. The sink was clogged.. there was stains and fingerprints all over the door and blankets.. the soap dispenser was broken just sitting in the tub.. sofa bed was filthy with no extra sheets or pillows in the room… and the closest parking was $35… not to mention I went down for breakfast there was nothing but coffee and a giant hole in the ceiling leaking water on both sides of the coffee counter
Reviewed on Sep 9, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
CA $798
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
8.4/10 Very good! (1,005 reviews)
The room had a good massage chair that worked well! The first day there was a fishy smell all across the property and the room smelled like it had been smoked in.
Reviewed on Sep 7, 2026
Eaton DC
Downtown Washington D.C.
CA $1,091
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.2/10 Wonderful! (1,614 reviews)
At first glance, the hotel’s mood and atmosphere is calm, cool and a bit groovy. It feels like stepping back into the 1970s where Motown and jazz filled the scene with style. Moody colors and textures filled the lobby. A vinyl record radio station was front
Reviewed on Sep 9, 2026
Ready to book your vacation to Highland?
Highland Hotel Deals
Washington Plaza Hotel
10 Thomas Circle NW Washington DC
Fully refundableReserve now, pay when you stay
CA $151
CA $175 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (5,464 reviews)
"Good"
Reviewed on Sep 9, 2026
Hilton Washington DC Capitol Hill
525 New Jersey Ave Nw Washington DC
Fully refundableReserve now, pay when you stay
CA $259
CA $300 total
Oct 4 - Oct 5
includes taxes & fees
9.2/10 Wonderful! (1,035 reviews)
"Great location, beautiful property, and wonderful staff. Definitely will return."
Reviewed on Sep 9, 2026
Omni Shoreham Hotel Washington DC
2500 Calvert St Nw Washington DC
Fully refundableReserve now, pay when you stay
CA $188
CA $265 total
Sep 11 - Sep 12
includes taxes & fees
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 $539 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?
- Choose your dates: The things you want to do in Highland and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
