A lighthouse on a rocky cliff surrounded by dense forest.

Owls Head Vacation Rentals

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Our top choices for Owls Head vacation rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (463 reviews)
"Great stay, great location."
United States
Jerold
The price is CA $178
CA $194 total
includes taxes & fees
Aug 23 - Aug 24
Trade Winds on the Bay

2. Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (90 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is CA $331
CA $378 total
includes taxes & fees
Aug 25 - Aug 26
Pine Grove Cottages

3. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
The price is CA $182
CA $537 total
includes taxes & fees
Sep 3 - Sep 4
Rustic Retreat Across From Lake; Family Friendly!

4. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
The price is CA $249
CA $675 total
includes taxes & fees
Sep 9 - Sep 10
Near Lakes, Bay & Trails! Historic Waldoboro Gem
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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Find out more about Owls Head

Everything you need to know about Owls Head vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Owls Head vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Owls Head vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Owls Head vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Owls Head. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Owls Head vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Owls Head vacation rentals we have selected for you start as low as CA $194 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Owls Head rentals

At Expedia, we put the best Owls Head vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Owls Head rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Owls Head vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Owls Head. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Are there vacation rentals in Owls Head?

Yes, you can find vacation rentals close to top sights in Owls Head, or you can select a more remote option if you're looking for relaxation. Owls Head is known for its museums and seaside. Make sure you have time to check out the wineries and forests during your trip.

What are some of the best vacation rentals in Owls Head?

Ocean Breeze: Visitors give good reviews to this Owls Head vacation home rental, which is near the beach and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Owls Head is Comfortable, Close to Town Home, with Oceanview..

How many vacation rentals will I find in Owls Head?

Choose from 44 Expedia vacation rentals in Owls Head for a memorable vacation.

What’s there to see and do in Owls Head?

Crescent Beach and Lucia Beach are a couple of scenic spots to enjoy the outdoors, whereas Owls Head Transportation Museum is one of the cultural attractions. Other places in town to visit include Owls Head State Park and Owls Head Lighthouse.

What’s a vacation rental in Owls Head like?

Vacation rentals are private properties you can book for a couple of days or more in Owls Head. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.