Highland Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
Save 100% on your flight
Price was $1,125, price is now $763 per person
$763
per person
Jun 3 - Jun 10
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
The Revolution Hotel
South End
Save 100% on your flight
Price was $1,580, price is now $1,100 per person
$1,100
per person
May 9 - May 16
found 15 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,914, price is now $1,337 per person
$1,337
per person
May 9 - May 16
found 15 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Furnished Apartment near BMC
South End
Save 100% on your flight
Price was $1,782, price is now $1,261 per person
$1,261
per person
Jun 3 - Jun 10
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this apartment in Boston. Enjoy free WiFi and laundry facilities. Popular attractions Copley Square and Boston Common are located nearby.
Courtyard by Marriott Boston Downtown/North Station
West End
Save 100% on your flight
Price was $2,056, price is now $1,476 per person
$1,476
per person
May 9 - May 16
found 15 hours ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and New England Aquarium are located nearby.
Top Hotel Deals
Best Western Merry Manor Inn
700 Main St South Portland ME
1.56 km from Highland
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
The Westin Portland Harborview
157 High St Portland ME
5.26 km from Highland
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
5.03 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
5.27 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Portland Harbor Hotel
468 Fore Street Portland ME
5.64 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
5.92 km from Highland
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
6.48 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
12.55 km from Highland
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hyatt Place Portland Downtown - Old Port Square
433 Fore St Portland ME
5.71 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
6.2 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
5.02 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Aloft Portland Downtown Waterfront ME
379 Commercial Street Portland ME
5.18 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
6.08 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, May 25 - Mon, Jun 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Mon, May 25 - Fri, May 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Mon, May 4 - Wed, May 13
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$202 Roundtrip, found 22 hours ago
$202
Roundtrip
found 22 hours ago
Sat, Jun 6 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago