Pleasant Point Vacation Packages

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Ready to book your vacation to Pleasant Point?

 

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Pleasant Point Hotel Deals

Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Nov 16 to Nov 17
CA $158
CA $191 total
Nov 16 - Nov 17
includes taxes & fees
7.4/10 Good! (476 reviews)
"The room was clean and comfortable. Staff was very helpful with dining suggestions for dinner and breakfast the next day."

Reviewed on Nov 10, 2026

Harborline Hotel
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
The price is CA $147 per night from Nov 15 to Nov 16
CA $147
CA $160 total
Nov 15 - Nov 16
includes taxes & fees
Trade Winds on the Bay
Harkness Brook Inn

Harkness Brook Inn

2.5 out of 5
337 Commercial St. Rockport ME
Get rates
Harkness Brook Inn
See all 1,411 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pleasant Point vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation to Pleasant Point costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Pleasant Point?
The off-season is the best time to head to Pleasant Point if you're trying to keep costs down. Another tip for scoring cheap Pleasant Point vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Pleasant Point?
The ideal duration of your Pleasant Point vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to hit all the leading attractions and explore some hidden spots along the way.
How to find the best Pleasant Point package deals?
Begin your search for a Pleasant Point package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Pleasant Point package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasant Point adventure off to a flying start.
Is it cheaper to book a Pleasant Point vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights individually. Better still, you can personalize your Pleasant Point getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pleasant Point?
If you have your Pleasant Point travel dates confirmed, book early to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Pleasant Point?

  1. Pick your travel dates: What you'd like to do in Pleasant Point and your preferred season will help you decide when to travel.
  2. Figure out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Pleasant Point.
  3. Determine how many days away: Start by listing all the sights and activities you want to get to in Pleasant Point. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Pleasant Point vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.