
Pleasant Point Vacations from $1,217
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Pleasant Point vacation packages
Price found within the past 48 hours. Click for updated prices.


Homeport Inn and Tavern
Price was $1,555, price is now $1,422 per person
$1,422
per person
Aug 13 - Aug 17
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Trade Winds on the Bay
Price was $1,865, price is now $1,742 per person
$1,742
per person
Sep 13 - Sep 17
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) 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 $1,962, price is now $1,853 per person
$1,853
per person
Sep 13 - Sep 17
found 18 hours ago
Roundtrip flight included
Cincinnati (CVG) 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
Don't see what you're looking for?
See all available trips from Columbus to Pleasant Point
View all tripsPleasant Point Hotel Deals

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
$152 nightly
The price is $166 total per night from Jul 20 to Jul 21
$166 total
Jul 20 - Jul 21
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 9 to Jul 10
$138 total
Jul 9 - Jul 10
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) |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Motels in Friendship
- Rv Parks in Port Clyde
- Cottages in Tenants Harbor
- Hotels near Tenants Harbor Marina
- Bristol Hotels
- B&B in Friendship
- Camden Hotels
- Resorts in Friendship
- Apartments in Tenants Harbor
- Motels in Cushing
- B&B in Cushing
- Cabin Rentals in Clark Island
- Brunswick Hotels
- Rockport Hotels
- Oceanfront Hotels in Boothbay Harbor
- Cheap Hotels in Port Clyde
- Cabin Rentals in Cushing
- Aparthotels in Port Clyde
- Friendship Hotels
- Hotels near Acadia National Park
- Guest Houses in Tenants Harbor
- Boothbay Harbor Hotels
- Vacation Homes in Cushing
- Pleasant Point Hotels
- Cabin Rentals in Friendship
- Damariscotta Hotels
- Cabin Rentals in Pleasant Point
- Motels in Port Clyde
- Cushing Hotels
- Thomaston Hotels
- Hotels with Restaurants in Clark Island
- Port Clyde Hotels
- B&B in Tenants Harbor
- Cottages in Friendship
- Inns in Port Clyde
- Augusta Hotels
- Rockland Hotels
- Farmstay in Port Clyde
- Tenants Harbor Hotels
- Extended Stay Hotels in Tenants Harbor
- Portland Hotels
- Monhegan Island Hotels
- New Harbor Vacations
- Rockland Breakwater Lighthouse
- Visit Clark Island
- Snow Marine Park
- Pemaquid Point Lighthouse Park
- Jan Kilburn Watercolor Studio and Gallery
- Damariscotta Vacations
- Visit Tenants Harbor
- Tenants Harbor Marina
- Rachel Carson Salt Pond Preserve
- Project Puffin Visitor Center
- Colonial Pemaquid State Historic Site
- Samoset Resort Golf Course
- Marshall Point Lighthouse
- Owls Head Transportation Museum
- Frances Perkins Center
- Visit Bremen
- Whaleback Shell Midden State Historic Site
- Rockland Vacations
- Visit Pleasant Point
- Camden Vacations
- Visit Rockland
- Pemaquid Beach Park
- Visit Friendship
- Owls Head Lighthouse
- Birch Point Beach State Park
- Rockland Harbor Park
- Visit Port Clyde
- Crescent Beach
- Rockland Ferry Terminal
- Maine Coastal Islands National Wildlife Refuge Visitor Center
- Warren Vacations
- Port Clyde Vacations
- Visit Cushing
- Buoy Park
- Ll Bean Flagship Store
- Sail Power and Steam Museum
- Maine State Prison Store
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















