Highland Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

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 ...
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
4.18 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 helpful ...
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 ...
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 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 ...
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 ...
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
5.49 km from Highland
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
4.69 km from Highland
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
4.7 km from Highland
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
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 ...
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
209 Fore St Portland ME
6.18 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 ...
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 ...
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 ...
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St Portland ME
8.5 km from Highland
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
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 ...
Don't see what you're looking for?
See all available properties in Highland
View all properties
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.

Delta
Sun, Jul 12 - Thu, Jul 30
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 6 hours ago
$147
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, Jul 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Jul 30, priced at $147 found 6 hours ago
Breeze Airways
Sat, May 16 - Wed, May 20
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, May 16 from Tampa Intl. to Portland Intl. Jetport, returning Wed, May 20, priced at $203 found 5 days ago
United
Sun, Feb 15 - Sat, Feb 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$224 Roundtrip, found 2 days ago
$224
Roundtrip
found 2 days ago
Select United flight, departing Sun, Feb 15 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Feb 21, priced at $224 found 2 days ago
American Airlines
Wed, Jul 15 - Tue, Jul 28
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$242 Roundtrip, found 6 hours ago
$242
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Jul 15 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Jul 28, priced at $242 found 6 hours ago
Southwest Airlines
Wed, May 13 - Mon, May 18
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$292 Roundtrip, found 15 hours ago
$292
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, May 13 from Orlando Intl. to Portland Intl. Jetport, returning Mon, May 18, priced at $292 found 15 hours ago