Pleasant Point Vacations from $343

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The Latest Pleasant Point vacation packages

Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $437, price is now $343 per person
$343
per person
Mar 11 - Mar 16
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Rockland (RKD)
8.4/10 Very Good! (312 reviews)
great value, nice large room, clean and everything needed. No continental breakfast offered but still good value

Reviewed on Jan 5, 2026

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Pleasant Point Hotel Deals

Hampton Inn & Suites Rockland

Hampton Inn & Suites Rockland

2.5 out of 5
190 New County Rd Thomaston ME
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $142 total per night from Jan 25 to Jan 26
$142 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (530 reviews)
everything

Reviewed on Jan 4, 2026

Hampton Inn & Suites Rockland
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
$129 nightly
The price is $141 total per night from Jan 7 to Jan 8
$141 total
Jan 7 - Jan 8
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
Super friendly staff. Clean and comfortable rooms. Good breakfast variety. Really loved that they have local maple syrup. Would stay again.

Reviewed on Dec 29, 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
$121 nightly
The price is $132 total per night from Jan 11 to Jan 12
$132 total
Jan 11 - Jan 12
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
Staff was very nice and the room was spotless. It was comfortable and cozy and convenient. I would stay here again

Reviewed on Jan 2, 2026

Flagship Inn and Suites
See all 1,267 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 $343 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.