Search Deals onHighland Vacation Packages
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
John Carver Inn & Spa
Plymouth Cultural District
Price was $976, price is now $705 per person
$705
per person
May 11 - May 17
found 23 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this spa hotel in Plymouth. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Richard Sparrow House and John Jenney Museum are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $3,196, price is now $1,892 per person
$1,892
per person
May 12 - May 16
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 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.
Beachside Village Resort
Price was $1,181, price is now $803 per person
$803
per person
May 11 - May 17
found 23 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this beach apartment in Falmouth. Enjoy free WiFi, an outdoor pool, and daily housekeeping. Our guests praise the property condition in our reviews. Popular attractions Surf Drive Beach and Falmouth Beach are located nearby.
The Revolution Hotel
South End
Save 100% on your flight
Price was $1,032, price is now $709 per person
$709
per person
May 12 - May 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,146, price is now $801 per person
$801
per person
May 12 - May 16
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.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $3,575, price is now $2,564 per person
$2,564
per person
May 12 - May 16
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.
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $1,254, price is now $903 per person
$903
per person
May 3 - May 9
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.
Portland Harbor Hotel
Downtown Portland
Price was $1,303, price is now $941 per person
$941
per person
May 11 - May 16
just found
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 Maine Mall and Cross Insurance Arena 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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed 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 ...
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 ...
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 ...
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 ...
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
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.
Sat, Aug 22 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, just found
$178
Roundtrip
just found
Sat, May 23 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$190 Roundtrip, found 14 hours ago
$190
Roundtrip
found 14 hours ago
Wed, May 27 - Tue, Jun 9
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$246 Roundtrip, found 11 hours ago
$246
Roundtrip
found 11 hours ago
Wed, Apr 15 - Mon, Apr 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$266 Roundtrip, found 7 hours ago
$266
Roundtrip
found 7 hours ago
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