Highland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Highland

Find the best Highland areas and neighborhoods for the activities you enjoy most. Learn more about Highland
Bug Light

Willard Beach

2 out of top 10 points of interest in this area

When in Willard Beach, you can plan a visit to Willard Beach and Spring Point Ledge Lighthouse, some noteworthy sights in the nearby area.

Find hotels in Willard Beach

Top hotels in Highland

Best Western Merry Manor Inn

Best Western Merry Manor Inn

2.5 out of 5
700 Main St South Portland ME
Fully refundableReserve now, pay when you stay
The price is S$141 per night from 22 Apr to 23 Apr
S$141
22 Apr - 23 Apr
includes taxes & fees
9/10 Wonderful! (1,028 reviews)
Really nice clean rooms, great hot tub and pool. Also a great breakfast and great staff

Reviewed on 9 Apr, 2026

Best Western Merry Manor Inn
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is S$210 per night from 16 Apr to 17 Apr
S$210
16 Apr - 17 Apr
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
We enjoyed our stay. The only boy issue was a stain on the box spring, which staff took care of almost immediately. Would definitely stay again

Reviewed on 12 Apr, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is S$207 per night from 19 Apr to 20 Apr
S$207
19 Apr - 20 Apr
includes taxes & fees
9.4/10 Exceptional! (1,195 reviews)
Disappointed with Friday dinner. Ordered simple burgers and they were burnt. Staff great, though

Reviewed on 12 Apr, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,453 properties in Highland
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.

Things to do

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Portland Golden Adventure Puzzle Quest and Tour

S$12
per adult
Portland Golden Adventure Puzzle Quest and Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$20
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Maine: Portland Smartphone-Based Walking Audio Tour

Maine: Portland Smartphone-Based Walking Audio Tour

S$15
per traveller
Maine: Portland Smartphone-Based Walking Audio Tour
See all activities in South Portland

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.