Highland Vacation Packages for 2026

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Top Hotel Deals

Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
700 Main St South Portland ME
1.56 km from Highland
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

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
5.26 km from Highland
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

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
5.03 km from Highland
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 ...
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
5.64 km from Highland
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 ...
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
5.27 km from Highland
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 Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
5.92 km from Highland
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

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
6.48 km from Highland
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

Old Orchard Beach Inn

2.5 out of 5
6 Portland Ave Old Orchard Beach ME
12.55 km from Highland
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. ...
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
5.71 km from Highland
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 ...
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
209 Fore St Portland ME
6.2 km from Highland
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 ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
5.02 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

3 out of 5
379 Commercial Street Portland ME
5.18 km from Highland
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 bar and ...
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
65 Commercial St Portland ME
6.08 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
4.78 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
LivAway Suites Portland-Scarborough

LivAway Suites Portland-Scarborough

2 out of 5
83 Mussey Rd Scarborough ME
4.18 km from Highland
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Beech Ridge Motor Speedway are located ...
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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

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Mon, May 25 - Mon, Jun 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, May 25 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Jun 1, priced at $177 found 2 days ago
Delta
Mon, May 25 - Fri, May 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, May 25 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, May 29, priced at $177 found 3 days ago
United
Mon, May 4 - Wed, May 13
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select United flight, departing Mon, May 4 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, May 13, priced at $177 found 2 days ago
American Airlines
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 8 from LaGuardia to Portland Intl. Jetport, returning Fri, Sep 11, priced at $202 found 1 day ago
Breeze Airways
Sat, Jun 6 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jun 6 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Jun 13, priced at $221 found 2 days ago