
Pleasant Point Vacations from $553
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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
Price was $944, price is now $818 per person
$818
per person
Jun 30 - Jul 3
found 10 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Rockland (RKD)
9.2/10 Wonderful! (200 reviews)
No TVs, no alarm clocks, no microwaves, no mini fridge = No superfluous stuff cluttering up the room with noise and light! Light, in fact, was my only real issue because it's an old inn and the door to our room had a gap at the top so when the motion sensor hall light came on (and stayed on for a long time) after anyone came upstairs, it was pretty bright. However, I pack a sleep mask because most places have an obnoxious amount of tech-related lights, so not a big deal. Still, this was by far the coziest, quietest, comfiest place we've stayed maybe ever. LOVED the spectacular view from our room (St George) and from the dining area. REALLY LOVED that we could walk across the causeway and take in the surroundings/stretch our legs without needing a car. Came at the wrong time of year to have dinner there, but greatly appreciated that the website and room guides listed lots of other options (mostly in Rockland, which is an easy trip with other fun stops along the way.) Breakfast was lovely. I've never liked grits in my life, but lemon and thyme do something magical for them. And the Craignair did something magical for us. I miss it already! THANK YOU!!
Reviewed on Nov 17, 2025

Glen Cove Inn & Suites
Price was $965, price is now $867 per person
$867
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rockland (RKD)
9.4/10 Exceptional! (1,000 reviews)
Property was clean, comfortable and we enjoyed our stay and would stay again .
Reviewed on May 12, 2026

Captain Sweetser's Inn
Price was $1,062, price is now $1,007 per person
$1,007
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rockland (RKD)
10/10 Exceptional! (130 reviews)
Wonderful stay at a lovely historic property. The room was very nice with a view of Penobscot Bay.
The hosts were very friendly and knowledgeable about the local history and community.
Reviewed on Oct 21, 2025
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The Country Inn at Camden Rockport
8 Country Inn Way Rockport ME
$126 nightly
The price is $138 total per night from May 14 to May 15
$138 total
May 14 - May 15
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
A great and reasonably priced room close to Camden. Zach was great and welcoming at check in. Hotel room had a nice sitting area, was recently reburbished and offered a decent included breakfast.
Reviewed on May 11, 2026

Trade Winds on the Bay
2 Park Dr Rockland ME
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $120 total per night from May 17 to May 18
$120 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (384 reviews)
Clean room and friendly staff
Reviewed on May 11, 2026

Harborline Hotel
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from May 17 to May 18
$151 total
May 17 - May 18
Total with taxes and fees
7.6/10 Good! (254 reviews)
Clean
Reviewed on May 7, 2026
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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