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.
DoubleTree by Hilton Boston North Shore
Price was $548, price is now $404 per person
$404
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Putnam House are located nearby.
Hotel AKA Back Bay
Back Bay
Save 100% on your flight
Price was $1,077, price is now $789 per person
$789
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, room service, 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.
Studio Allston Hotel
Brighton
Save 100% on your flight
Price was $751, price is now $554 per person
$554
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. 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 Harvard Square and Fenway Park are located nearby.
The Boston Hotel
Brighton
Save 100% on your flight
Price was $807, price is now $607 per person
$607
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Courtyard by Marriott Boston Andover
Price was $641, price is now $484 per person
$484
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Andover. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Lawrence Public Library and Methuen Memorial Music Hall are located nearby.
The Revolution Hotel
South End
Price was $766, price is now $586 per person
$586
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
San Antonio (SAT) 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.
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 ...
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 ...
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 ...
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 ...
Ramada Plaza by Wyndham Portland
155 Riverside St Portland ME
8.5 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
1.71 km from Highland
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
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 ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
4.89 km from Highland
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
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 ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
3.95 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 helpful ...
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 ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
8.24 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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 ...
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.
Wed, Sep 2 - Wed, Sep 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Sat, Aug 1 - Thu, Aug 6
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Sat, Aug 1 - Thu, Aug 6
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago