Highland Beach Packages (Flight + Hotel)

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Top Highland Beach Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hillside Inn & Suite

Hillside Inn & Suite

2.5 out of 5
Price was ฿44,121, price is now ฿42,129 per person
฿42,129
per person
22 Oct - 28 Oct
found 13 hours ago
Return direct flight included
Bangkok (BKK) to Baltimore (BWI)
7.6/10 Good! (156 reviews)

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
Price was ฿59,999, price is now ฿53,805 per person
฿53,805
per person
22 Oct - 28 Oct
found 13 hours ago
Return direct flight included
Bangkok (BKK) to Baltimore (BWI)
8.6/10 Excellent! (599 reviews)
Hotel room was very clean although the air conditioning unit was very noisy. I believe hotel is on the older side and might be the reason why unit was so noisy. Staff was very nice and the breakfast offered early at 6 AM is nice as we like to get on the road early. Will stay again.

Reviewed on 25 Jul 2026

The Carriage Inn B&B

The Carriage Inn B&B

3.5 out of 5
Price was ฿61,418, price is now ฿55,924 per person
฿55,924
per person
22 Oct - 28 Oct
found 13 hours ago
Return direct flight included
Bangkok (BKK) to Baltimore (BWI)
9.6/10 Exceptional! (452 reviews)
The Carriage House was beautiful in a cute, historic area. I was impressed with the cleanliness and how helpful and accommodating the staff were. Breakfast was delicious too.

Reviewed on 25 Jul 2026

Holiday Inn Martinsburg by IHG

Holiday Inn Martinsburg by IHG

3 out of 5
Price was ฿49,441, price is now ฿47,035 per person
฿47,035
per person
22 Oct - 28 Oct
found 13 hours ago
Return direct flight included
Bangkok (BKK) to Baltimore (BWI)
9/10 Wonderful! (719 reviews)

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

2.5 out of 5
Price was ฿54,202, price is now ฿52,102 per person
฿52,102
per person
22 Oct - 28 Oct
found 13 hours ago
Return direct flight included
Bangkok (BKK) to Baltimore (BWI)
9.2/10 Wonderful! (1,008 reviews)
Room was ok, pool was fun , great breakfast

Reviewed on 1 Aug 2026

Top hotels in Highland Beach

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ฿3,882 per night from 5 Aug to 6 Aug
฿3,882
฿5,569 total
5 Aug - 6 Aug
includes taxes & fees
9/10 Wonderful! (1,904 reviews)
"This is our 2nd visit here and primarily chosen for location, historical significance and cleanliness. Located directly in the hub of beautiful Annapolis, it is easy walking and convenient to all shops, restaurants and the harbor. The rooms are nicely decorated with all the amenities needed for a ..."

Reviewed on 1 Aug 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is ฿3,945 per night from 9 Aug to 10 Aug
฿3,945
฿4,498 total
9 Aug - 10 Aug
includes taxes & fees
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ฿3,845 per night from 23 Aug to 24 Aug
฿3,845
฿4,383 total
23 Aug - 24 Aug
includes taxes & fees
8.8/10 Excellent! (1,067 reviews)
"Very affordable and much better than the hotels in the area in this price range. Free parking, good service, comfortable and clean rooms. I will stay here again."

Reviewed on 1 Aug 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,214 properties in Highland Beach
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.

What to do in Highland Beach

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

฿1,339
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

฿321
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

฿1,071
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
See all activities in Highland Beach

Frequently asked questions

How much does a Highland Beach holiday package cost?
You'll find cheap prices from ฿42,129 on Expedia for your Highland Beach escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Highland Beach costs.
What are the cheapest months to go to Highland Beach?
You can typically find lower prices and better availability in January, February and March. Explore our cheap Highland Beach holiday packages and you could land some excellent off-season deals.
How many days is enough for Highland Beach?
The ideal duration for your Highland Beach holiday depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Highland Beach package deals?
Use Expedia's handy filters to help you find some tempting Highland Beach package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Highland Beach package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Highland Beach holiday as a package?
You can enjoy significant savings on your next Highland Beach retreat by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Highland Beach?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Highland Beach break.
How to plan a trip to Highland Beach?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Highland Beach.
  2. Set a budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Highland Beach. Then, select a property that matches your budget, whether that's an economical option or a lavish getaway.
  3. Decide your trip length: Think about how long you want to spend exploring Highland Beach. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, lock in the right Highland Beach holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.