Highland Vacations from $251

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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!

The Latest Highland vacation packages

Price found within the past 48 hours. Click for updated prices.
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $377, price is now $251 per person
$251
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,765 reviews)
The room was kind of dirty, especially the shower. At dinner I found plastic wrap cooked into my food. The waitress was amazing and took care of us. Close to the Camden Yards field which was nice.

Reviewed on Jun 20, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $475, price is now $298 per person
$298
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,022 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $707, price is now $444 per person
$444
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (1,866 reviews)
Bed had a wear to it where I rolled . Tub was rusted with grout having mold . The product container was suppose to hang on the wall but kept falling off and breaking the bottles so they did not work. Def not worth the price we paid. It was in a great vicinity.

Reviewed on Jun 20, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $669, price is now $429 per person
$429
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,194 reviews)
The check-in and check-out process was quick and hassle-free, and everyone at the property was incredibly friendly and helpful. The location is fantastic, with easy access to all the museums and great food spots.

Reviewed on Jun 19, 2026

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Save 100% on your flight
Price was $531, price is now $347 per person
$347
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,437 reviews)
I took a suite, I think the least of what needs to be there is complementary water bottles daily

Reviewed on Jun 18, 2026

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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 Jun 28 to Jun 29
$126 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (5,202 reviews)
"It’s okay"

Reviewed on Jun 21, 2026

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
$169 nightly
The price is $191 total per night from Jul 12 to Jul 13
$191 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (3,464 reviews)
"We enjoyed this hotel in DC. The rooms are quite small, with the bathroom door actually hitting the toilet in opening. They made a good use of small space. A couple of maintenance issues that were not make or break, property was adorable. Being forced to valet at $65 a night felt a bit much, and ..."

Reviewed on Jun 20, 2026

Hamilton Hotel Washington DC
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
2500 Calvert St Nw Washington DC
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $192 total per night from Jul 10 to Jul 11
$192 total
Jul 10 - Jul 11
Total with taxes and fees
9/10 Wonderful! (2,353 reviews)
"This property exceeded our expectations My husband and I were truly amazed. The beds were so comfortable that my husband asked me to find out the name brand of the mattress so that we could order one for our home. They have great amenities and have everything covered even down to a playroom for children. ..."

Reviewed on Jun 20, 2026

Omni Shoreham Hotel
See all 4,169 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.

Find the Best Highland Vacation Packages

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)
Population
1,050

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Frequently asked questions

How much does a Highland vacation package cost?
You'll find cheap prices from $251 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.