Pleasant Point Vacations from $1,217

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The Latest Pleasant Point vacation packages

Price found within the past 48 hours. Click for updated prices.
The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $1,439, price is now $1,217 per person
$1,217
per person
Sep 27 - Oct 1
just found
Roundtrip flight included
Dallas (DFW) to Rockland (RKD)
9.2/10 Wonderful! (200 reviews)
Synday brunch was very good

Reviewed on Dec 22, 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
$201 nightly
The price is $219 total per night from Jul 9 to Jul 10
$219 total
Jul 9 - Jul 10
Total with taxes and fees
9.6/10 Exceptional! (1,004 reviews)
"Clean and spacious room. Comfortable beds. Great staff. Pool and hot tub both clean and nice. I would definitely stay again."

Reviewed on Jul 6, 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
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $166 total per night from Jul 9 to Jul 10
$166 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"The room was decent. This is definitely an older hotel, but our stay was perfectly fine. The price was was excellent compared to the other hotels a bit closer to the harbor. The pool looked very nice, we just didn't have a chance to use it. The free breakfast was really good."

Reviewed on Jul 7, 2026

Flagship Inn and Suites
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $138 total per night from Jul 9 to Jul 10
$138 total
Jul 9 - Jul 10
Total with taxes and fees
7.6/10 Good! (286 reviews)
"Clean, reasonable size bedroom and bathroom. Excellent on-site parking. Walking or close driving distance to restaurants and museums."

Reviewed on Jul 7, 2026

Harborline Hotel
See all 1,563 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.

Find the Best Pleasant Point Vacation Packages

Pleasant Point Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Knox County Regional Airport (RKD)

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Frequently asked questions

How much does a Pleasant Point vacation package cost?
Offering excellent value package deals from $1,217 on Expedia, you'll be surprised at how little a vacation to Pleasant Point costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pleasant Point?
You can usually find lower rates and greater availability in November, December and January. Take a look at our cheap Pleasant Point vacation packages and you could land some great off-season deals.
How many days is enough for Pleasant Point?
Typically, a handful of days is enough to tick off the major sights during your Pleasant Point vacation. But if you'd like to have time to rest or take day trips, think about extending your trip.
How to find the best Pleasant Point package deals?
Finding a cheap Pleasant Point package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Pleasant Point package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pleasant Point vacation as a package?
You can enjoy significant savings on your next Pleasant Point break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pleasant Point?
If you're planning an impromptu Pleasant Point adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Pleasant Point vacation packages?
Your Pleasant Point break is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.