
Pleasant Point Vacations from $1,313
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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
Price was $1,448, price is now $1,313 per person
$1,313
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rockland (RKD)
8.6/10 Excellent! (419 reviews)
I enjoyed my stay here very much, which was conveniently located near the windjammer docks which was the main reason that brought me here… staff is very courteous attentive to detail, and there is one hell of a great steamed muscle restaurant called Park Street Grille which I had to go to three times! During the time I was initially there, the main parking lot was being resurfaced, but as I didn’t need a car didn’t immediately affect me…
Reviewed on Jul 5, 2026

Harborline Hotel
Price was $1,789, price is now $1,615 per person
$1,615
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rockland (RKD)
7.6/10 Good! (282 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


Homeport Inn and Tavern
Price was $1,568, price is now $1,459 per person
$1,459
per person
Aug 13 - Aug 18
found 1 hour ago
Roundtrip non-stop flight included
Baltimore (BWI) to Rockland (RKD)
9.6/10 Exceptional! (296 reviews)
We could not have been happier with our recent 3-day stay at the HomePort Inn in Searsport, Maine. We knew that this was a good location for what we wanted to do... Exploratory trips to places like Camden and Castine. But what we were not prepared for, especially for the price quoted, was the luxury of the rooms and the high quality of the entire facility. Innkeepers Allison and Arno are lovely. The downstairs tavern was a perfect place for dinner one night, as well as a cocktail. This is a lovely old sea captain's mansion with high ceilings and beautiful appointments. Lots of public rooms downstairs, including a billiard table and a kind of game room library. Breakfast was great and offered on a long, lovely glassed-in porch with a view out too beautiful garden with flowering bushes and shrubs. The ocean is a short walk down a quiet side street. A walk of several blocks brings you into the downtown which has a couple of very good restaurants. Honestly we could have hung out here and never left the property, but we had lots to do and see. We hope to come back. We cannot recommend this place more highly.
Reviewed on Jun 27, 2026

Glen Cove Inn & Suites
Price was $1,445, price is now $1,364 per person
$1,364
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rockland (RKD)
9.4/10 Exceptional! (1,005 reviews)
The woman at the front desk was such a ray of light, both in the afternoon and in the morning. She was smiling and genuinely pleasant and helpful. The property is well maintained and it looked like they really took pride is keeping it up. The beds were comfortable and the water pressure and temp as they should be. Breakfast was really nice, especially for being listed as continental. There were muffins, bagels, hard boiled eggs, cereal, oatmeal, juices, and a waffle iron. We’d stay again if ever in the area.
Reviewed on Jul 6, 2026
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The Country Inn at Camden Rockport
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

Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $169 total per night from Jul 12 to Jul 13
$169 total
Jul 12 - Jul 13
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

Harborline Hotel
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $138 total per night from Jul 8 to Jul 9
$138 total
Jul 8 - Jul 9
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
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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