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.
The Westin Boston Seaport District
Seaport District
Save 100% on your flight
Price was $1,251, price is now $874 per person
$874
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The Atlas Hotel
Allston
Save 100% on your flight
Price was $1,722, price is now $1,099 per person
$1,099
per person
Jun 25 - Jun 30
found 22 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,950, price is now $1,335 per person
$1,335
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $4,245, price is now $2,966 per person
$2,966
per person
Jun 25 - Jun 30
found 16 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Arcadian Hotel
Coolidge Corner
Save 100% on your flight
Price was $1,373, price is now $1,053 per person
$1,053
per person
Jun 25 - Jun 30
found 17 hours ago
Roundtrip non-stop flight included
West Palm Beach (PBI) 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 Harvard Square are located nearby.
Hotel Commonwealth
Fenway–Kenmore
Save 100% on your flight
Price was $2,382, price is now $1,842 per person
$1,842
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square 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 ...
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 ...
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 ...
HomeAwhile
205 Southborough Drive Scarborough ME
4.77 km from Highland
Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Thompson's Point are located ...
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 ...
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 ...
Inn at St John Portland In-Town
939 Congress St Portland ME
4.82 km from Highland
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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 ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
4.78 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. 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 ...
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.
Tue, Jun 2 - Thu, Jun 11
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Sat, Jun 6 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Mon, Aug 3 - Sat, Aug 8
LGA
LaGuardia
PWM
Portland Intl. Jetport
$157 Roundtrip, found 22 hours ago
$157
Roundtrip
found 22 hours ago
Tue, Jun 2 - Thu, Jun 11
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Fri, Jun 12 - Mon, Jun 15
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$247 Roundtrip, found 16 hours ago
$247
Roundtrip
found 16 hours ago