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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Owls Head holiday rentals

An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

1. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (83 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is HK$1,236
HK$3,399 total
includes taxes & fees
1 Nov - 2 Nov
Harbor/🦞 Pound Access & Views from Large Deck
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

2. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (85 reviews)
"The property was wonderful! Our group of 5 adults were very comfortable and satisfied with our stay of 3 nights. We were in town for a family reunion, and enjoyed the great amenities of the property as we spent cherished time with our extended family. Comfortable beds, relaxing common areas and great location."
United States
christoohey1
The price is HK$1,589
HK$4,666 total
includes taxes & fees
16 Oct - 17 Oct
Oceanview Bungalow Style Home in Owls Head
A room with a large window offering a view of a snowy landscape and a body of water.

3. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (102 reviews)
"Great location close to town"
United States
Rich W.
The price is HK$1,373
HK$2,772 total
includes taxes & fees
15 Nov - 16 Nov
Comfortable, Close to Town Home, with Oceanview.
Lobby sitting area

4. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (516 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
The price is HK$681
HK$742 total
includes taxes & fees
15 Nov - 16 Nov
Trade Winds on the Bay
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

5. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (36 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is HK$763
HK$1,191 total
includes taxes & fees
20 Oct - 21 Oct
Simplicity-Just what you need! STR24-20
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

6. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (57 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is HK$903
HK$2,053 total
includes taxes & fees
27 Oct - 28 Oct
2 Bedroom Close to Town Home
A modern kitchen with a stainless steel refrigerator, a coffee maker, and a sink.

7. In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (55 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is HK$2,068
HK$4,504 total
includes taxes & fees
28 Oct - 29 Oct
In-town, coastal + relaxing in Rockland
A bedroom with a bed, bedside tables, a dresser, a nightstand, a lamp, a vase with flowers, a framed picture, and a wall-mounted clock.

8. Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58

Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58
Rockland
10.0 out of 10, Exceptional, (3 reviews)
"Perfect stay"
United States
Kayla G.
Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58
A wooden deck with Adirondack chairs and a grill.

9. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (15 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is HK$989
HK$1,967 total
includes taxes & fees
9 Nov - 10 Nov
Bright 2-Bedroom Apartment Near Downtown Thomaston
Exterior

10. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (6 reviews)
"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...
United States
Christopher H.
The price is HK$957
HK$1,925 total
includes taxes & fees
21 Oct - 22 Oct
Romantic Coastal Escape near Harbor
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

11. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (41 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is HK$1,122
HK$2,327 total
includes taxes & fees
9 Nov - 10 Nov
Peaceful, Centrally Located Home with Seasonal River Views
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

12. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (44 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

13. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
Fully Updated Airy Historic Home in West Rockport
A pond surrounded by trees, with two wooden chairs facing the water.

14. Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Lincolnville
8.0 out of 10, Very good, (17 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
A coastal town with boats docked at a marina, surrounded by lush greenery and hills.

15. Pine Grove Cottages

Pine Grove Cottages
2.5 star property
Lincolnville
9.8 out of 10, Exceptional, (93 reviews)
"Wonderful quiet place, The Host was a great person."
United States
clinch
The price is HK$1,796
HK$2,056 total
includes taxes & fees
22 Oct - 23 Oct
Pine Grove Cottages
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

16. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.4 out of 10, Very good, (5 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is HK$1,295
HK$2,010 total
includes taxes & fees
19 Oct - 20 Oct
Come Spring Farm Airstream , Lake & farm animals
A calm lake with boats docked at a pier, surrounded by trees and hills.

17. Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden

Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
Lincolnville
9.8 out of 10, Exceptional, (17 reviews)
"Quant and cozy little cottage out in the peaceful quiet wooded area. Loved this place. Plenty of towels, washer and dryer, plenty of kitchen items. Will definitely stay again when in the area."
United States
Ruthanne
Peaceful 2-bedroom cottage in charming Lincolnville, near lake, winery & Camden
A two-story house with a front porch, a chimney, and a garage.

18. Cozy cottage -Close to Downtown Camden!

Cozy cottage -Close to Downtown Camden!
Camden
9.6 out of 10, Exceptional, (34 reviews)
"This property was clean, the kitchen was well appointed, it was close to downtown and the beds were very comfortable. I would stay here again or reccomend it to others."
United States
Abby S.
The price is HK$2,315
HK$4,354 total
includes taxes & fees
14 Nov - 15 Nov
Cozy cottage -Close to Downtown Camden!
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

19. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.8 out of 10, Excellent, (16 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is HK$1,570
HK$2,229 total
includes taxes & fees
20 Oct - 21 Oct
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A cabin with a wooden deck and a white door.

20. Pine Grove Cottages: Cottage 4: Studio Cottage - Pet Friendly

Pine Grove Cottages: Cottage 4: Studio Cottage - Pet Friendly
Lincolnville
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and quaint cottage in the woods! The cabin was very comfortable. The host provided some awesome local eating options. Would highly recommend to others and will stay here again!"
United States
Taylor B.
The price is HK$1,722
HK$2,134 total
includes taxes & fees
22 Oct - 23 Oct
Pine Grove Cottages: Cottage 4: Studio Cottage - Pet Friendly
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

Trade Winds on the Bay

Trade Winds on the Bay

10/10 Excellent
"Nice little ocean view with a little balcony. Places to eat in walking distance. Nice little gift shop."
Anonymous traveller 1-night trip
Posted 5 hours ago
Trade Winds on the Bay

Find out more about Owls Head

Search for holiday rentals in Owls Head on Expedia! You can easily find your home rentals, villas, holiday apartments in Owls Head using one of the methods below:

  • View our selection of featured holiday rentals in Owls Head
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  • Enter your travel dates to view the best deals on holiday rentals in Owls Head while they last

Look no further and take a look at our great range of rental properties in Owls Head!

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. Some other top choices in Owls Head are Oceanview Bungalow Style Home in Owls Head and Comfortable, Close to Town Home, with Oceanview..

How many holiday rentals will I find in Owls Head?

Choose from 40 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.