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

Trade Winds on the Bay

3.5 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
8.4/10 Very Good! (245 reviews)
The Trade Winds is an awesome location for visiting the Maine Lobster Festival, as it’s literally across the street. Be aware that being that close does have a disadvantage if you go to sleep early since you can hear the live entertainment from the main stage of the festival. We enjoyed it though since we could open the balcony door and enjoy the music from the comfort of our room. The staff were very kind and helpful. Being able to park our car and walk everywhere was another benefit.

Reviewed on Aug. 2, 2025

Harborline Hotel

Harborline Hotel

3 out of 5
per person
Oct 16 - Oct 19
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Rockland (RKD)
7.8/10 Good! (90 reviews)
This was near the marina and rhe view was beautiful. Bed was comfortable and rhe room spacious.

Reviewed on Aug. 12, 2025

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
per person
Oct 2 - Oct 6
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
9.6/10 Exceptional! (1,000 reviews)
Our balcony needed some work. Room and public area comfortable and clean

Reviewed on Aug. 11, 2025

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Owls Head Hotel Deals

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is CA $296 per night from Sep 1 to Sep 2
CA $296
CA $558 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (74 reviews)
"Perfect location for downtown Rockland! View of the ocean and quiet neighbors. The communication was excellent and easy arrival checkout."

Reviewed on Jul. 30, 2025

Comfortable, Close to Town Home, with Oceanview.
Lovely Waterfront Owls Head Home w/ Own Beach

Lovely Waterfront Owls Head Home w/ Own Beach

Owls Head
9.8/10 Exceptional! (51 reviews)
"Beautiful property! We really enjoyed our stay"

Reviewed on Aug. 7, 2025

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Lovely Waterfront Owls Head Home w/ Own Beach
Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head

Owls Head
9.8/10 Exceptional! (55 reviews)
"Location was beautiful, property was immaculate, but it’s lacking some basics! Here is what is needed: kitchen towels, potholders, a tea kettle, a coffeemaker, wine glasses, drinking glasses other than plastic, bath mats, saucepans (there were only stock pots) . But most importantly, the listing ..."

Reviewed on Jul. 25, 2025

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Oceanview Bungalow Style Home in Owls Head
See all 1,044 properties in Owls Head
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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Discover the most popular places to visit in Owls Head

Owls Head Lighthouse

Owls Head Lighthouse

Find out about the history of Owls Head when you take a trip to Owls Head Lighthouse. Wander the waterfront in this romantic area.

Owls Head Lighthouse

Breakwater Vineyards

You can enjoy a tasting or tour at Breakwater Vineyards during your travels to Owls Head. While you're in the area, stroll along the waterfront.

Breakwater Vineyards

Frequently asked questions

How much does an Owls Head vacation package cost?
You can pick up a vacation package to this popular destination from CA $608 on Expedia. However, how much your vacation to Owls Head costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Owls Head?
To score cheap Owls Head vacation packages, plan your getaway outside of peak times such as public holidays. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Owls Head?
Usually, a handful of days is enough to tick off the top attractions during your Owls Head vacation. But if you'd like to have time to unwind or take day trips, consider extending your itinerary.
How to find the best Owls Head package deals?
Use Expedia's handy filters to find some terrific Owls Head package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Owls Head package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book an Owls Head vacation as a package?
You can enjoy significant savings on your next Owls Head retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value 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 Owls Head?
If you're planning an impromptu Owls Head trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Owls Head?

  1. Choose your travel dates: What you want to do in Owls Head and your preferred season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Owls Head.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Owls Head. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick an Owls Head vacation package that brings all your bookings together.

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