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Highland Vacation Packages

Highland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $422, price is now $291 per person
$291
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Beverly Commons and Salem Willows Beach are located nearby.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $610, price is now $356 per person
$356
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $512, price is now $317 per person
$317
per person
Feb 26 - Mar 3
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.
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

3 out of 5
Spring Hill
Save 100% on your flight
Price was $553, price is now $349 per person
$349
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Somerville. 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 Harvard Square and TD Garden are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,875, price is now $1,198 per person
$1,198
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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.
The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Save 100% on your flight
Price was $678, price is now $438 per person
$438
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $426, price is now $292 per person
$292
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,219, price is now $844 per person
$844
per person
Feb 26 - Mar 3
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 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 Boston Common and TD Garden are located nearby.

3-4 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $323, price is now $221 per person
$221
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,299, price is now $880 per person
$880
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $412, price is now $283 per person
$283
per person
Mar 22 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,509, price is now $1,038 per person
$1,038
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

5-7 Night Vacations in Highland

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $512, price is now $317 per person
$317
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was $1,860, price is now $1,284 per person
$1,284
per person
Mar 7 - Mar 13
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,349, price is now $1,255 per person
$1,255
per person
Mar 18 - Mar 23
found 3 hours ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $610, price is now $356 per person
$356
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Cheap Hotel Deals in Highland

Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
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 ...
Opens in a new windowBest Western Merry Manor Inn
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
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 ...
Opens in a new windowThe Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
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 ...
Opens in a new windowClarion Hotel Portland Airport ME
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Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
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 ...
Opens in a new windowLong Creek Hotel by IHG
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
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 ...
Opens in a new windowPortland Harbor Hotel
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
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 ...
Opens in a new windowHoliday Inn Portland-By the Bay by IHG
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
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. ...
Opens in a new windowOld Orchard Beach Inn
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
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 ...
Opens in a new windowPortland Regency Hotel & Spa
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.

American Airlines
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 12 hours ago
$200
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $200 found 12 hours ago
Delta
Mon, Apr 6 - Mon, Apr 13
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 13 hours ago
$209
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Apr 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Apr 13, priced at $209 found 13 hours ago
JetBlue Airways
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $220 found 5 days ago
JetBlue Airways
Wed, May 27 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$276 Roundtrip, found 5 hours ago
$276
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $276 found 5 hours ago