Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
Wish there was coffee in the lobby at all times

Reviewed on Jul. 8, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
Great staff. Nice rooms. Would stay here again.

Reviewed on Jul. 8, 2025

Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,006 reviews)
overall good. Cant find hair dryer in the room.

Reviewed on Jul. 5, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 14 - Sep 21
just found
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9/10 Wonderful! (1,851 reviews)
Everyone was great, then staff was amazing. The only issue we had was the TEXT System for room service was not good at all. We tried to us it 4 times and it did not work at all. The entire staff was amazing. We has a credit for the room service but was not aware. Once I brought it to the attention of the floor manager. I totally spaced on her name. She was blonde, wore a flowery blouse and had on khaki pants. Was super helpful. The front desk staff was also great, I had many of them help me out but Terri and Elvis were the names that stood out.

Reviewed on Jul. 9, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
The property was beautiful and has an opportunity to eat at Dogon restaurant! Excellent food!

Reviewed on Jul. 11, 2025

Ready to book your vacation to Highland?

 

Choose your dates

Highland Hotel Deals

Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jul 20 to Jul 21
CA $149
CA $173 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (4,432 reviews)
"Very centralized. Decent overall"

Reviewed on Jul. 9, 2025

Washington Plaza Hotel
Omni Shoreham Hotel
Omni Shoreham Hotel
4 out of 5
2500 Calvert St Nw, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Jul 26 to Jul 27
CA $144
CA $206 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,978 reviews)
"Loved the pool"

Reviewed on Jul. 11, 2025

Omni Shoreham Hotel
Hamilton Hotel Washington DC
Hamilton Hotel Washington DC
4 out of 5
1001 14th St NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Aug 4 to Aug 5
CA $175
CA $245 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,475 reviews)
"The property offered a location with proximity to all major DC sites and convenient access to a nearby metro. Additionally, the water filling station in the lobby provided much needed hydration for our family during the summer weather. The staff were always courteous and helpful even while tending ..."

Reviewed on Jul. 10, 2025

Hamilton Hotel Washington DC
See all 3,839 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this top destination from CA $700 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.