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.
Eurostars The Boxer
West End
Price was $1,141, price is now $849 per person
$849
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Newbury Boston
Back Bay
Save 100% on your flight
Price was $2,477, price is now $1,554 per person
$1,554
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,158, price is now $1,448 per person
$1,448
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $3,315, price is now $2,237 per person
$2,237
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Revere Hotel Boston Common
Bay Village
Price was $1,244, price is now $907 per person
$907
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Colonnade Hotel Back Bay
Back Bay
Price was $1,442, price is now $1,135 per person
$1,135
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park 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 ...
Long Creek Hotel by IHG
171 Philbrook Ave South Portland ME
4.18 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 ...
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 ...
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 ...
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 ...
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 ...
Canopy by Hilton Portland Waterfront
9 Center Street Portland ME
5.49 km from Highland
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Tru by Hilton Portland Airport Area
369 Maine Mall Road South Portland ME
4.69 km from Highland
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
DoubleTree by Hilton Hotel Portland
363 Maine Mall Rd South Portland ME
4.7 km from Highland
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
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 ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
6.18 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 ...
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 ...
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 ...
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.
Sat, May 16 - Wed, May 20
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Sat, Apr 11 - Tue, Apr 14
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 6 hours ago
$209
Roundtrip
found 6 hours ago
Sun, Feb 15 - Sat, Feb 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Sun, Feb 15 - Sat, Feb 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Wed, May 13 - Mon, May 18
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$292 Roundtrip, found 8 hours ago
$292
Roundtrip
found 8 hours ago