Pleasant Point Vacations from $280

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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 $388, price is now $280 per person
$280
per person
Nov 10 - Nov 15
found 17 hours ago
Roundtrip flight included
Washington (WAS) to Rockland (RKD)
8.4/10 Very Good! (268 reviews)
Front desk folks were very helpful

Reviewed on Sep 25, 2025

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $1,410, price is now $1,147 per person
$1,147
per person
Oct 26 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
9.6/10 Exceptional! (288 reviews)
This beautiful antique mansion was the perfect place to begin exploring. Convenient to many attractions. Onsite tavern was a bonus. Breakfasts were perfect.hard to find charm and great hospitality.

Reviewed on Aug 13, 2025

Glen Cove Inn & Suites

Glen Cove Inn & Suites

2.5 out of 5
Price was $882, price is now $745 per person
$745
per person
Oct 26 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
9.4/10 Exceptional! (977 reviews)
Great place with lots of charm. Clean room and convenient location.

Reviewed on Sep 25, 2025

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
Price was $791, price is now $713 per person
$713
per person
Oct 26 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rockland (RKD)
9.6/10 Exceptional! (1,005 reviews)
Spacious room and sitting area with fireplace. Breakfast good. Would highly recommend

Reviewed on Sep 25, 2025

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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
$119 nightly
The price is $129 total per night from Sep 29 to Sep 30
$129 total
Sep 29 - Sep 30
Total with taxes and fees
7.6/10 Good! (174 reviews)
"Excellent stay. Very convenient inside and out.n"

Reviewed on Sep 24, 2025

Harborline Hotel
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
$149 nightly
The price is $162 total per night from Oct 26 to Oct 27
$162 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,031 reviews)
"Spacious room and sitting area with fireplace. Breakfast good. Would highly recommend"

Reviewed on Sep 25, 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
$172 nightly
The price is $187 total per night from Oct 26 to Oct 27
$187 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (1,022 reviews)
"Staff was very friendly. Simple facilities but neat"

Reviewed on Sep 23, 2025

Flagship Inn and Suites
See all 1,329 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?
Offering excellent value package deals from $280 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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Explore a world of travel with Expedia

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