Pleasant Point Vacation Packages

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Top Pleasant Point Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harborline Hotel

Harborline Hotel

3 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
8.6/10 Excellent! (53 reviews)
Location The hotel is directly across the road from the harbor and with in walking distance of downtown

Reviewed on Jul. 23, 2025

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
8.4/10 Very Good! (227 reviews)
Great stay, nice and easy. Very uncomplicated check in. Close to everything in town! This is our second time staying here and we'll definitely be back!

Reviewed on Jul. 23, 2025

East Wind Inn

East Wind Inn

2.5 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
9.4/10 Exceptional! (109 reviews)
Amazing environment! Perfect for a weekend getaway

Reviewed on Jul. 17, 2025

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Pleasant Point Hotel Deals

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 CA $284 per night from Aug 25 to Aug 26
CA $284
CA $310 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
Great place to stay!!
"Staying at the Country Inn is always as expected. Clean, friendly, comfy, and well appointed rooms with an added attention to details. The fire pit area out back is a lovely spot to sit and relax in the evening. The Country in is close to Camden and all the quaint seaside communities along Rt. 1. ..."

Reviewed on Jul. 20, 2025

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 CA $157 per night from Jul 27 to Jul 28
CA $157
CA $204 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Very reasonably priced and nice property with pool. My son and I enjoyed our stay!"

Reviewed on Jul. 22, 2025

Flagship Inn and Suites
Ledges by the Bay

Ledges by the Bay

2.5 out of 5
930 Commercial St, Rockport, ME
The price is CA $215 per night from Aug 5 to Aug 6
CA $215
CA $235 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Clean"

Reviewed on Jul. 23, 2025

Ledges by the Bay
See all 1,355 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.
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Frequently asked questions

How much does a Pleasant Point vacation package cost?
You can pick up a vacation package to this top destination from CA $760 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.