Pleasant Point Holidays

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The Annual Holiday Sale

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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

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 9 Mar to 10 Mar
S$180
9 Mar - 10 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
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.

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* 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.