Highlands Vacations from $508
Book a Hotel + Flight or Car together to unlock savings
Your Highlands Vacation
Your next escape is calling your name with a vacation package to Highlands. Fun, food and nothing but good times — you're bound to find it in this neighborhood. Some nearby attractions to check out during your trip to Highlands include University of Massachusetts Lowell, Tsongas Arena and Lowell Memorial Auditorium. Stop dreaming and start doing. When you're ready to lock in your next vacation to Highlands, Expedia will help you get there.
The Latest Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Hotel Portsmouth
Downtown
Save 100% on your flight
Price was $765, price is now $508 per person
$508
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
Room clean. Staff helpful although we were assigned a room at check in only to find someone else in that room!
Nice European style breakfast but tea and coffee were not hot. Sufficient easy parking.
Reviewed on Jul 2, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,208, price is now $1,378 per person
$1,378
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
Nantucket Inn
Save 100% on your flight
Price was $2,346, price is now $1,463 per person
$1,463
per person
Aug 21 - Aug 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (720 reviews)
The place is really great! The staff by far were the best part, extremely friendly and helpful with everything! We also had a place to store our luggage for when we wanted to go explore but were unable to check-in. The lobby and room were very nice and clean, as well as the amenities like the pool. The shuttle made it very convenient to get around too. Overall wonderful stay and place!
Reviewed on Jul 1, 2026
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $1,408, price is now $920 per person
$920
per person
Aug 21 - Aug 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
Loved it here! Everyone was friendly and helpful.
Reviewed on Jul 1, 2026
Chatham Tides
Save 100% on your flight
Price was $2,384, price is now $1,572 per person
$1,572
per person
Aug 21 - Aug 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (716 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10
Reviewed on Jul 2, 2026
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
South Lowell
Though South Lowell might not have many top sights, you can venture to the surrounding area to see attractions like Merrimack Repertory Theater and Lowell Memorial Auditorium.
Highlands Hotel Deals
Bedford Plaza Hotel - Boston
340 Great Road Bedford MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from Jul 3 to Jul 4
$96 total
Jul 3 - Jul 4
Total with taxes and fees
7/10 Good! (996 reviews)
"It was okay"
Reviewed on Jul 1, 2026
Holiday Inn Hotel & Suites Boston - Peabody by IHG
1 Newbury St Peabody MA
Fully refundable
$136 nightly
The price is $152 total per night from Jul 19 to Jul 20
$152 total
Jul 19 - Jul 20
Total with taxes and fees
7.2/10 Good! (1,004 reviews)
"We had a pleasant stay. The location is convenient for a visit to Salem."
Reviewed on Jul 2, 2026
Lakeside Inn
595 North Ave Wakefield MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jul 19 to Jul 20
$113 total
Jul 19 - Jul 20
Total with taxes and fees
7.6/10 Good! (2,370 reviews)
"Ok"
Reviewed on Jul 2, 2026
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.
Stay near popular Highlands attractions
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.