
Owls Head Vacation Packages
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Your Owls Head Vacation
Lock in a Owls Head vacation package and get ready for a fantastic adventure. Noted for its coastal scenery and spectacular views, there's plenty to keep you on the move in this captivating city. Every trip to Owls Head needs a well-crafted itinerary. Fill yours with attractions like Samoset Resort Golf Course, Rockland Breakwater Lighthouse and Sandy Beach. Browse Expedia's extensive range of travel options and book your ultimate vacation to Owls Head today.
Top Owls Head Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Trade Winds on the Bay
Price was CA $1,021, price is now CA $879 per person
CA $879
per person
Sep 25 - Sep 30
just found
Roundtrip flight included
Toronto (YTO) 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 CA $1,243, price is now CA $1,097 per person
CA $1,097
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Rockland (RKD)
7.6/10 Good! (282 reviews)
The location of the hotel was great for us very close to the downtown ,newly renovated ,quiet ,had a breakfast room down at the end of the floor ,very close
Reviewed on Jul 5, 2026

Homeport Inn and Tavern
Price was CA $1,870, price is now CA $1,673 per person
CA $1,673
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 CA $1,660, price is now CA $1,548 per person
CA $1,548
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Owls Head Hotel Deals

1-BR waterfront apt with wood-burning sauna & pool table
Owls Head ME

Comfortable, Close to Town Home, with Oceanview.
Owls Head ME
The price is CA $355 per night from Jul 13 to Jul 14
CA $355
CA $638 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (93 reviews)
"Excellent view and beautiful yard. Super comfy furniture and mattress. Great Location."
Reviewed on Jun 21, 2026

Oceanfront with Spectacular Views of Penobscot Bay
Owl's Head ME
9.8/10 Exceptional! (48 reviews)
"Rosie's Cottage is a vintage but timeless gem in many ways. Unbelievable waterfront setting and peaceful and quiet day and night. Hosted by Rosemary with responsiveness to ensure comfort and privacy. The cottage and deck are unique and welcoming and fully equipped, even stocked with many essentials ..."
Reviewed on Jun 28, 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.
Stay near popular Owls Head attractions
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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.







