Search Deals onHighland Vacation Packages
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit
Price was $756, price is now $565 per person
$565
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
84 Main
Save 100% on your flight
Price was $1,172, price is now $749 per person
$749
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
The Docent’s Collection – Thompson Block
Downtown Portland
Save 100% on your flight
Price was $1,108, price is now $722 per person
$722
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,907, price is now $1,247 per person
$1,247
per person
Apr 3 - Apr 7
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $1,007, price is now $701 per person
$701
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
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 and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
Portland Regency Hotel & Spa
Downtown Portland
Save 100% on your flight
Price was $975, price is now $718 per person
$718
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
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 our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $1,440, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 7
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
The Westin Portland Harborview
Downtown Portland
Price was $790, price is now $599 per person
$599
per person
Apr 7 - Apr 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) 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 State Theatre and Portland Stage are located nearby.
3-4 Night Vacations in Highland
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Highland
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Highland
Best Western Merry Manor Inn
700 Main St South Portland ME
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 ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
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 Harbor Hotel
468 Fore Street Portland ME
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
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 ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
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 ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
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 ...
Long Creek Hotel by IHG
171 Philbrook Ave South Portland ME
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 ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
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 ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 6 days ago
$203
Roundtrip
found 6 days ago
Fri, Mar 6 - Wed, Mar 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Tue, Mar 17 - Wed, Mar 25
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago