Highland Vacation Packages

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was CA $701, price is now CA $493 per person
CA $493
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
8/10 Very Good! (1,007 reviews)
You have to pay for the parking even though the parking lot empty and there are not many cars

Reviewed on Aug. 26, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was CA $1,114, price is now CA $736 per person
CA $736
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
9.8/10 Exceptional! (39 reviews)
The staff is extremely friend, adn the foods in the restaurant are wonderful

Reviewed on Aug. 26, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was CA $956, price is now CA $640 per person
CA $640
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
8.6/10 Excellent! (1,006 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug. 12, 2025

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Price was CA $1,032, price is now CA $693 per person
CA $693
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (WAS)
8.2/10 Very Good! (1,005 reviews)
Front desk was super helpful and responsive

Reviewed on Aug. 23, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $743, price is now CA $507 per person
CA $507
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful place! Amazing staff!

Reviewed on Aug. 21, 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 $137 per night from Aug 28 to Aug 29
CA $137
CA $159 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (4,562 reviews)
"Easy access to all the museums and sites walkable in most cases."

Reviewed on Aug. 23, 2025

Washington Plaza 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 $140 per night from Aug 31 to Sep 1
CA $140
CA $204 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (2,661 reviews)
"The hotel was very beautiful, but we were a little disappointed that the front entrance was blocked off for construction. When we got into our room it wasn't exactly as described (which wasn't a big deal) and there was a hair clip on the floor, and the bathroom was very visibly not clean. We ended ..."

Reviewed on Aug. 25, 2025

Hamilton Hotel Washington DC
The Henley Park Hotel

The Henley Park Hotel

4 out of 5
926 Massachusetts Ave NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Aug 28 to Aug 29
CA $142
CA $164 total
Aug 28 - Aug 29
includes taxes & fees
9/10 Wonderful! (1,158 reviews)
"A bit old but great. Very nice staff"

Reviewed on Aug. 25, 2025

The Henley Park Hotel
See all 3,895 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.
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Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this top destination from CA $493 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.