Highland Vacations from $312

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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.
  • Jan 27 - Feb 2

    Convention center Indoor free parking + Flight

    Downtown Baltimore
    6 nights
    4.0 star property
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    $520
    $312
    per traveler
    found 1 day ago
    Convention center Indoor free parking
  • Jan 27 - Feb 2

    Sofitel Washington DC Lafayette Square + Flight

    Downtown Washington D.C.
    6 nights
    5.0 star property
    9.0/10 - Wonderful (1,301 reviews)
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    $1,082
    $639
    per traveler
    found 23 hours ago
    Sofitel Washington DC Lafayette Square
  • Jan 27 - Feb 2

    Pendry Baltimore + Flight

    Fells Point
    6 nights
    5.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    $1,930
    $1,151
    per traveler
    found 1 day ago
    Pendry Baltimore
  • Jan 27 - Feb 2

    Eurostars Saint Gregory Dupont Circle Georgetown + Flight

    Downtown Washington D.C.
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "I really enjoyed my stay at this hotel. It was an easy place to navigate from they had restaurants in a bar on the property. The staff was very kind and I love my room in the space we were in. I would absolutely stay here again."
    Reviewed November 11, 2026
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    Save 100% on your flight
    $833
    $528
    per traveler
    found 1 day ago
    Eurostars Saint Gregory Dupont Circle Georgetown
  • Jan 27 - Feb 2

    The Hotel at Arundel Preserve + Flight

    Arundel Mills
    6 nights
    3.5 star property
    9.4/10 - Exceptional (2,031 reviews)
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    $569
    $363
    per traveler
    found 1 day ago
    The Hotel at Arundel Preserve

Where to stay near Highland

Highland, Maryland offers a delightful mix of family-friendly activities and romantic spots, making it perfect for any traveler. Explore nearby Maryland cities for vibrant culture and outdoor adventures, while enjoying the welcoming neighborhoods that make this region so special.

Clarksville

For travelers seeking a memorable trip, Clarksville offers a charming blend of outdoor adventures, entertainment, and family-friendly activities. Enjoy the nearby urban park and beach, or immerse yourself in the vibrant local scene with theater, music concerts, and shopping. With attractions like the historic University of Maryland, College Park, and the bustling Baltimore Convention Center, there's something for everyone. Located about 2 miles from Highland, Clarksville is a smart choice for your next getaway.

Fulton

Plan your stay in Fulton, a top-rated choice for family travelers and weekend getaways looking for a blend of city excitement and natural charm. With attractions such as the historic University of Maryland, College Park, the serene Patuxent River, and the inviting Maple Lawn Dog Park, Fulton offers a delightful escape for all ages. Located about 3 miles from Highland, it serves as a smart hotel booking choice for those eager to explore local shopping and entertainment options.

Brinklow

If you are a family-oriented traveler, look no further than Brinklow, a charming village that offers a delightful mix of nature and urban experiences. Enjoy nearby attractions such as the historic University of Maryland, College Park, and the lively Howard County Fairgrounds, perfect for family fun. Brinklow also provides easy access to various shopping centers and outdoor parks, ensuring a memorable stay. Located about 3 miles from Highland, Brinklow is an excellent choice for your vacation lodging.

Ashton-Sandy Spring

Ashton-Sandy Spring stands out as a prime spot for travelers seeking a blend of nature and urban experiences. This welcoming city offers adventure activities like a thrilling zipline ropes course, alongside serene visits to local parks such as Norwood Park. With attractions like the University of Maryland and Howard University nearby, visitors can enjoy both educational and recreational pursuits. Located about 4 miles from Highland, Ashton-Sandy Spring is an ideal choice for your next getaway.

Spencerville

Travelers visiting the area often choose Spencerville, especially families and nature enthusiasts seeking a vibrant experience. With attractions like the University of Maryland, College Park, and Howard University, guests can immerse themselves in educational and cultural pursuits. The nearby Maple Lawn Dog Park adds a touch of outdoor fun for pet lovers. Spencerville is about 4 miles from Highland, making it an easy choice for those looking to explore the region. This charming locale offers a delightful blend of activities, making it a smart booking option.

Frequently Asked Questions

How much does a Highland vacation package cost?

You'll find cheap prices from $312 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.