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.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Price was $1,157, price is now $828 per person
$828
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Stay at this hotel in Woburn. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Burlington Mall and MarketStreet Lynnfield are located nearby.
The Westin Boston Seaport District
Seaport District
Save 100% on your flight
Price was $1,589, price is now $1,149 per person
$1,149
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip non-stop flight included
Seattle (SEA) 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 Artisan At Tuscan Village, Salem, A Tribute Portfolio Hotel
Price was $1,803, price is now $1,428 per person
$1,428
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Book a stay at this luxury hotel in Salem. Enjoy free WiFi, an outdoor pool, and 3 restaurants. Popular attractions Canobie Lake Park and The Mall at Rockingham Park are located nearby.
Holiday Inn Hotel & Suites Boston - Peabody by IHG
Price was $1,120, price is now $931 per person
$931
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Book a stay at this business-friendly hotel in Peabody. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Salem Witch Museum and MarketStreet Lynnfield are located nearby.
Crowne Plaza Boston - Woburn by IHG
Price was $1,236, price is now $1,030 per person
$1,030
per person
Jun 24 - Jun 30
found 2 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Book a stay at this business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction Burlington Mall is located nearby.
The Westin Portland Harborview
Downtown Portland
Price was $1,885, price is now $1,602 per person
$1,602
per person
Jun 24 - Jun 30
found 3 hours ago
Roundtrip flight included
Seattle (SEA) to Portland (PWM)
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 rooms in our reviews. Popular attractions Thompson's Point and Maine Mall 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 1 day ago
$157
Roundtrip
found 1 day 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 19 hours ago
$247
Roundtrip
found 19 hours ago