Pleasant Point Vacations from $293

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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 $369, price is now $293 per person
$293
per person
Jan 13 - Jan 16
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rockland (RKD)
8.4/10 Very Good! (292 reviews)
Basic room , clean and perfect for our stay.

Reviewed on Nov 8, 2025

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
Price was $389, price is now $360 per person
$360
per person
Jan 13 - Jan 16
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rockland (RKD)
9.6/10 Exceptional! (1,023 reviews)
Zac was super helpful at checkin

Reviewed on Nov 10, 2025

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Pleasant Point Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
$172 nightly
The price is $188 total per night from Nov 24 to Nov 25
$188 total
Nov 24 - Nov 25
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
I would give this 5 stars, but... The good: very pet friendly. The rooms are well suited for pets, and BONUS: there's an amazing pretty park literally right next door over a pretty wood bridge - there are loops from 1/2 to 2 miles. Bed was comfy. There were ample outlets, lots of bedside lights. ...

Reviewed on Nov 2, 2025

Flagship Inn and Suites
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $127 total per night from Dec 11 to Dec 12
$127 total
Dec 11 - Dec 12
Total with taxes and fees
7.6/10 Good! (215 reviews)
The room was very clean and staff was friendly and courteous.

Reviewed on Nov 7, 2025

Harborline Hotel
Glen Cove Inn & Suites

Glen Cove Inn & Suites

2.5 out of 5
866 Commercial St., Route 1, Rockport, ME
9.4/10 Exceptional! (1,001 reviews)
The bungalows are so cute. The service is great. I hope now that the season is over they do a deep clean in the corners and things like the black mildew on the tub plug and touching up chipping paint. Can’t wait to return in the spring.

Reviewed on Oct 28, 2025

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Glen Cove Inn & Suites
See all 1,256 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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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 $293 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.