Highland Vacations from $219

Book a Hotel + Flight or Car together to unlock savings

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!

The Latest Highland vacation packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $324, price is now $219 per person
$219
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
This was a great option with the hotel on the college campus for convenience to visit with grandkids but also walking distance for great restaurants. Very clean, friendly and accommodating staff. Highly recommend it.

Reviewed on Sep 11, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $571, price is now $332 per person
$332
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (WAS)
9.4/10 Exceptional! (1,010 reviews)
Great stay! Large room, comfortable bed and good food options.

Reviewed on Sep 19, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $465, price is now $290 per person
$290
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (WAS)
8/10 Very Good! (1,015 reviews)
It's a good hotel but far from the city's attractions.

Reviewed on Sep 28, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,018, price is now $640 per person
$640
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (WAS)
9.8/10 Exceptional! (55 reviews)
Details. This place had high end features.

Reviewed on Sep 12, 2025

Kimpton Hotel Monaco Washington DC by IHG

Kimpton Hotel Monaco Washington DC by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,171, price is now $762 per person
$762
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
8.4/10 Very Good! (1,004 reviews)
Our stay was very pleasant, we were staying during a wedding and several shows in the area at the same time. The hotel handled everything with ease and were pleasant to speak with. From the Valet to the front desk everyone ensured a smooth visit.

Reviewed on Sep 28, 2025

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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
$109 nightly
The price is $126 total per night from Oct 1 to Oct 2
$126 total
Oct 1 - Oct 2
Total with taxes and fees
8.6/10 Excellent! (4,687 reviews)
"Belcony room was awesome"

Reviewed on Sep 25, 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
$200 nightly
The price is $227 total per night from Oct 2 to Oct 3
$227 total
Oct 2 - Oct 3
Total with taxes and fees
8.6/10 Excellent! (2,814 reviews)
"Loved the room and the location."

Reviewed on Sep 28, 2025

Hamilton Hotel Washington DC
citizenM Washington DC Capitol

citizenM Washington DC Capitol

4 out of 5
550 School St SW, Washington, DC
$169 nightly
The price is $196 total per night from Oct 20 to Oct 21
$196 total
Oct 20 - Oct 21
Total with taxes and fees
8.8/10 Excellent! (2,811 reviews)
"Enticing art display and happy colors everywhere, very relaxed and well thought environment, friendly but still professional staff. Near public transportation, all the museums and monuments at walkable distance."

Reviewed on Sep 22, 2025

citizenM Washington DC Capitol
See all 3,967 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'll find cheap prices from $219 on Expedia for your Highland escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Highland costs.
What are the cheapest months to go to Highland?
If you're looking to book a cheap Highland vacation package, consider traveling in January, September and December. You'll generally find better prices on accommodations and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Highland?
With a well-organized travel plan, you can easily hit the main Highland attractions in a handful of days. But if you want to discover hidden gems or take day trips, consider booking your Highland vacation for longer.
How to find the best Highland package deals?
Landing a cheap Highland package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most pocket-friendly Highland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Highland trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Highland?
If you're planning an impromptu Highland trip, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Highland vacation packages?
Secure your perfect escape to Highland with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.