A lighthouse on a rocky cliff surrounded by dense forest.

Owls Head Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Owls Head holiday rentals

Lobby sitting area

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 NZ$236
includes taxes & fees
24 Aug - 25 Aug
Trade Winds on the Bay
Boating

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 NZ$459
includes taxes & fees
25 Aug - 26 Aug
Pine Grove Cottages
Cottage (2 Bedrooms) | Interior

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 NZ$653
includes taxes & fees
24 Aug - 25 Aug
Rustic Retreat Across From Lake; Family Friendly!
House (3 Bedrooms) | Front of property

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 NZ$821
includes taxes & fees
9 Sept - 10 Sept
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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Top Owls Head Hotel Reviews

Whitehall

Whitehall

10/10 Excellent
"I loved this hotel. It was clean, charming and so close to town. The beds were so comfortable and the sheets were butter soft. I actually looked them up on line to buy them, but sadly the company only sells to hotels. The staff was lovely and I really enjoyed sitting outside with tea or wine on the rocking chairs. I would stay again for sure."
anne 2-night trip
Posted 3 hours ago
Whitehall

Find out more about Owls Head

Everything you need to know about Owls Head holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Owls Head holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Owls Head holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Owls Head holiday rentals we have selected for you start as low as NZ$236 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 holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Owls Head?

Yes, there are holiday rentals close to the most popular sights in Owls Head, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Owls Head has to offer?

Ocean Breeze: This highly rated holiday home rental in Owls Head is near the beach and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday 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 holiday rentals will I find in Owls Head?

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

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 holiday rental in Owls Head like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Owls Head. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.