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.
Harborline Hotel

Harborline Hotel

3 out of 5
Price was CA $1,195, price is now CA $1,107 per person
CA $1,107
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rockland (RKD)
7.6/10 Good! (124 reviews)
Great location and friendly staff

Reviewed on Aug. 22, 2025

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was CA $1,283, price is now CA $1,194 per person
CA $1,194
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rockland (RKD)
8.4/10 Very Good! (250 reviews)
It was very hands off-- you go, retrieve your key from the lock box and let yourself in. But it is a gorgeous old building built like a fancy plantation - castle, in the middle of a small coastal town in pristine Maine, with a pool and a fitness center. I didn't realize it at first, but my room had a hallway to another living room area, with a balcony to sit and watch the sunrise from. Wow! Yeah, it's a great place.

Reviewed on Aug. 14, 2025

Glen Cove Inn & Suites

Glen Cove Inn & Suites

2.5 out of 5
Price was CA $1,213, price is now CA $1,188 per person
CA $1,188
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rockland (RKD)
9.4/10 Exceptional! (955 reviews)
Check-in was easy, the room was clean and included a small refrigerator and coffee maker, and the breakfast was perfect. We thoroughly enjoyed our visit and would not hesitate to stay here again.

Reviewed on Aug. 20, 2025

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was CA $1,305, price is now CA $1,280 per person
CA $1,280
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rockland (RKD)
9/10 Wonderful! (188 reviews)
The inn is a unique place, in a pleasant way. The owners are wonderful at making you feel at home in their establishment. It's homey with its small, clean rooms. Our room had a private bathroom and a beautiful view. The breakfast was delicious, everything is made from scratch, the ingredients are obviously fresh and locally sourced (I had forgotten what real eggs taste like). The dinner at the restaurant below was also memorable. We highly recommend this place.

Reviewed on Aug. 23, 2025

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was CA $1,304, price is now CA $1,279 per person
CA $1,279
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rockland (RKD)
9.8/10 Exceptional! (283 reviews)
This beautiful antique mansion was the perfect place to begin exploring. Convenient to many attractions. Onsite tavern was a bonus. Breakfasts were perfect.hard to find charm and great hospitality.

Reviewed on Aug. 13, 2025

Ready to book your vacation to Owls Head?

 

Choose your dates

Owls Head Hotel Deals

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is CA $268 per night from Sep 1 to Sep 2
CA $268
CA $524 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.
Owls Head Village Post Office

Owls Head Village Post Office

Owls Head
9.8/10 Exceptional! (149 reviews)
"Amazing! Every detail of the post office was so well thought out! It felt like staying in a cozy house museum. We couldn’t believe the garden area either. My kids never wanted to leave- and are still asking when we can go back. (Just a note- my 3 year old did need to be carried on the stairs due ..."

Reviewed on Aug. 6, 2025

Get rates
Owls Head Village Post Office
Lovely Waterfront Owls Head Home w/ Own Beach

Lovely Waterfront Owls Head Home w/ Own Beach

Owls Head
9.8/10 Exceptional! (52 reviews)
"Well maintained home with a wonderful view."

Reviewed on Aug. 21, 2025

Get rates
Lovely Waterfront Owls Head Home w/ Own Beach
See all 1,050 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 $1,107 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.