Search Deals onHighland Vacation Packages
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
Price was $871, price is now $636 per person
$636
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hyannis Harbor and Mayflower Beach are located nearby.
Raffles Boston
Back Bay
Price was $3,233, price is now $2,357 per person
$2,357
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Ogunquit River Inn & Suites
Save 100% on your flight
Price was $1,002, price is now $655 per person
$655
per person
Jun 4 - Jun 9
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $1,646, price is now $1,129 per person
$1,129
per person
Jun 4 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Thompson's Point and Cross Insurance Arena are located nearby.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,182, price is now $838 per person
$838
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Docent's Collection at 121 Middle Street
Downtown Portland
Save 100% on your flight
Price was $1,727, price is now $1,230 per person
$1,230
per person
Jun 4 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and N.W. Barrett Gallery are located nearby.
Grasshopper Inn
Save 100% on your flight
Price was $1,863, price is now $1,341 per person
$1,341
per person
Jun 4 - Jun 9
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this inn in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $2,844, price is now $2,065 per person
$2,065
per person
May 29 - Jun 4
just found
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Fire Museum 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 ...
The Westin Portland Harborview
157 High St Portland ME
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
Hyatt Place Portland Downtown - Old Port Square
433 Fore 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 breakfast ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
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 ...
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.
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 12 hours ago
$157
Roundtrip
found 12 hours ago
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 17 hours ago
$185
Roundtrip
found 17 hours ago
Wed, May 20 - Thu, May 28
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 15 hours ago
$207
Roundtrip
found 15 hours ago
Wed, May 27 - Tue, Jun 9
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago