Search Deals onHighland Vacation Packages
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay
Back Bay
Price was $1,139, price is now $869 per person
$869
per person
Nov 27 - Dec 1
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel 1868
Agassiz
Price was $1,642, price is now $1,334 per person
$1,334
per person
Nov 28 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Encore Boston Harbor are located nearby.
All Seasons Inn & Suites Smithfield Providence
Price was $1,058, price is now $895 per person
$895
per person
Nov 22 - Nov 29
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Smithfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bally's Lincoln and Beirne Stadium are located nearby.
Battery Wharf Hotel, Boston Waterfront
North End
Save 100% on your flight
Price was $1,482, price is now $876 per person
$876
per person
Dec 2 - Dec 7
found 21 hours 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 breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,713, price is now $1,967 per person
$1,967
per person
Dec 2 - Dec 7
found 21 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 Faneuil Hall Marketplace and Boston Harbor are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $1,429, price is now $1,062 per person
$1,062
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
The Inn at Hastings Park, Relais & Chateaux - Boston
Lexington Green Historic District
Save 100% on your flight
Price was $2,016, price is now $1,589 per person
$1,589
per person
Nov 27 - Dec 1
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.
Encore Boston Harbor
Price was $1,272, price is now $1,006 per person
$1,006
per person
Nov 27 - Dec 1
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden 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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Quality Inn & Suites South Portland
738 Main Street 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 ...
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 ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Cross Insurance ...
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 ...
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.
Thu, Nov 12 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$191 Roundtrip, found 8 hours ago
$191
Roundtrip
found 8 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 1 hour ago
$192
Roundtrip
found 1 hour ago
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, just found
$201
Roundtrip
just found
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 22 hours ago
$207
Roundtrip
found 22 hours ago
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