Pleasant Point 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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top hotels in Pleasant Point

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (353 reviews)
Nice room. Roku tv. Good internet. King size bed was a tad soft for my taste but comfy. Had a partial ocean view. Nice pool with hot tub and sauna. Gym had a lot of equipment. Beautiful lobby with coffee shop. Rockland is walkable from hotel. Lots of good food. We took ferry to Vinal Island for a ...

Reviewed on 6 Mar, 2026

Get rates
Trade Winds on the Bay
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way Rockport ME
Fully refundableReserve now, pay when you stay
The price is S$180 per night from 8 Mar to 9 Mar
S$180
8 Mar - 9 Mar
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
As usual, a great stay.

Reviewed on 26 Feb, 2026

The Country Inn at Camden Rockport
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
The price is S$189 per night from 12 Mar to 13 Mar
S$189
12 Mar - 13 Mar
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Clean room great amenities

Reviewed on 6 Mar, 2026

Flagship Inn and Suites
See all 1,322 properties in Pleasant Point
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.

Explore a world of travel with Expedia

* 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.