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Highland Vacation Packages

3-4 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 $779, price is now $541 per person
$541
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was $1,891, price is now $870 per person
$870
per person
May 12 - May 16
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 $2,498, price is now $1,629 per person
$1,629
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,281, price is now $890 per person
$890
per person
May 22 - May 26
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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,002, price is now $655 per person
$655
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was $1,561, price is now $908 per person
$908
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $1,014, price is now $711 per person
$711
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,305, price is now $837 per person
$837
per person
May 30 - Jun 6
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
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 ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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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
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
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
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 ...
Opens in a new windowHyatt Place Portland Downtown - Old Port Square
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
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 ...
Opens in a new windowHampton Inn Portland Downtown - Waterfront
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.

United
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 20 hours ago
$157
Roundtrip
found 20 hours ago
Select United flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Jun 17, priced at $157 found 20 hours ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$181 Roundtrip, found 5 hours ago
$181
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $181 found 5 hours ago
Breeze Airways
Wed, May 20 - Thu, May 28
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 23 hours ago
$207
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, May 20 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Thu, May 28, priced at $207 found 23 hours ago
American Airlines
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
Select American Airlines flight, departing Wed, May 27 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Tue, Jun 9, priced at $264 found 1 day ago