Search Deals onHighland Vacation Packages
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Save 100% on your flight
Price was $1,459, price is now $976 per person
$976
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 Moody Beach and Ogunquit Beach are located nearby.
The Ritz-Carlton, Boston
Downtown Boston
Price was $5,025, price is now $3,437 per person
$3,437
per person
Jun 24 - Jun 29
found 4 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) 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 Faneuil Hall Marketplace are located nearby.
Furnished Apartment Near Longwood
North Brookline
Price was $2,349, price is now $1,728 per person
$1,728
per person
Jun 24 - Jun 29
found 4 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.
The Newbury Boston
Back Bay
Price was $3,248, price is now $2,397 per person
$2,397
per person
Jun 24 - Jun 29
found 4 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) 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 Copley Square and Boston Common are located nearby.
Raffles Boston
Back Bay
Price was $4,212, price is now $3,122 per person
$3,122
per person
Jun 24 - Jun 29
found 4 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) 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.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $2,576, price is now $1,541 per person
$1,541
per person
Jun 30 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Sea Crest Beach Resort
Save 100% on your flight
Price was $2,161, price is now $1,453 per person
$1,453
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Boston (BOS)
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Cataumet Arts Center are located nearby.
Chatham Tides
Save 100% on your flight
Price was $2,436, price is now $1,641 per person
$1,641
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Birmingham (BHM) to Boston (BOS)
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red River Beach and Forest Beach 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 ...
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 ...
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 ...
HomeAwhile
205 Southborough Drive Scarborough ME
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Maine Mall and Thompson's Point are located ...
Inn at St John Portland In-Town
939 Congress St Portland ME
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 ...
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 ...
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 ...
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.
Mon, Jun 1 - Sun, Jun 14
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 5 hours ago
$187
Roundtrip
found 5 hours ago
Sat, Jun 6 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Fri, Jul 3 - Sat, Jul 4
LGA
LaGuardia
PWM
Portland Intl. Jetport
$202 Roundtrip, found 9 hours ago
$202
Roundtrip
found 9 hours ago