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 $465 per person
CA $465
per person
Oct 28 - Oct 31
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
8/10 Very Good! (968 reviews)
People camping on the medium strip between highways. Stranger in front of hotel door cornered me and talked for over 30 minutes when all I wanted to do is get in my room and chill.

Reviewed on Aug. 18, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was CA $1,661, price is now CA $970 per person
CA $970
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
9.8/10 Exceptional! (28 reviews)
The hotel is a one-minute walk from Dupont Circle station. I had not ridden the DC metro in 20+ years and Cortez the DOO walked me through the lines and stations with a map. Not only friendly but thoroughly knowledgeable of the area and helpful, 10/10 customer service. There is a stunning restaurant Casamara in the hotel which has a simple, well-executed menu. Again, customer service was outstanding in the restaurant. There is also a rooftop bar. Parking is valet. Control room service or even locking/unlocking your door with a private link to your mobile.

Reviewed on Aug. 15, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Price was CA $2,499, price is now CA $1,497 per person
CA $1,497
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
9.4/10 Exceptional! (1,002 reviews)
Beautiful hotel, friendly and helpful staff, clean rooms, clean and nice pool, amazing spa!

Reviewed on Aug. 18, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,462, price is now CA $943 per person
CA $943
per person
Oct 7 - Oct 10
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on Jul. 21, 2025

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was CA $1,057, price is now CA $690 per person
CA $690
per person
Oct 10 - Oct 13
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.8/10 Excellent! (1,821 reviews)
I really enjoyed staying at a smaller hotel with charm! The staff is so nice and the location is great. Would stay here again.

Reviewed on Aug. 16, 2025

Ready to book your vacation to Highland?

 

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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 22 to Aug 23
CA $137
CA $158 total
Aug 22 - Aug 23
includes taxes & fees
8.6/10 Excellent! (4,549 reviews)
"It was great!"

Reviewed on Aug. 17, 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 $203 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (2,634 reviews)
"From arrival to departure, the Valet, Porter, House Cleaning and Front Desk personnel were corteous, helpful, and attentive. The room was clean, and all amenities nice."

Reviewed on Aug. 16, 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 26 to Aug 27
CA $142
CA $165 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (1,148 reviews)
"Beautiful property, lovely staff"

Reviewed on Aug. 16, 2025

The Henley Park Hotel
See all 3,889 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 $465 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.