Holiday houses in Owls Head

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Top-rated holiday rentals in Owls Head

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Top Guest favourite
The kitchen area features a spacious countertop with dark cabinetry and modern appliances. Bright, sloped ceilings are complemented by large windows that provide abundant natural light. A cozy living area is visible, adorned with comfortable seating and decorative elements that reflect the coastal theme.
Apartment in Owls Head
4.95 out of 5 average rating, 113 reviews

Oceanview Escape near Maine Beaches

Located at the end of a private road you will find the area very peaceful with beautiful ocean view sunrises and sunsets and lots of wildlife sightings. This cozy 1000 square foot apartment has been recently renovated for a clean coastal vibe. The house was originally hand built in 2000 by the owner. You will notice the craftsmanship detail, built ins, hand made furniture and unique nautical style throughout the apartment. The kitchen is fully stocked and equipped with stove, full fridge and a new microwave and dishwasher. The living space provides a 50 inch smart TV and queen pull out sofa. Enjoy the vast ocean views from the large living room picture windows. Watch the boats cruising through Penobscot Channel or a local lobsterman hauling their traps. The bedroom offers a queen bed and plenty of closet/storage space. There is a large jacuzzi tub and separate hand tiled shower in the bathroom. Spacious deck off the kitchen/living area provides an outdoor dining area and grill. Enjoy dinner or drinks taking in the salty ocean air and views. At the base of the entry stairs is a separate patio space with propane fire pit shared amongst both living spaces. Located behind the apartment is an adorable playhouse with slide, saucer swings and a rock climbing wall that is shared amongst the neighborhood. Please play at your own risk. WiFi included

Top Guest favourite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 430 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top Guest favourite
A charming cottage is situated amidst trees, with a gravel driveway leading to the entrance. A soft sunset is visible in the background, casting gentle hues of pink and purple across the sky, providing a serene backdrop to the peaceful setting.
Guesthouse in Cushing
4.97 out of 5 average rating, 111 reviews

Look! River Run Cottage on tidal salt waterfront

Maine the way life should be is not just an expression at River Run its a way of life. Located in Andrew Wyeth country (town of Cushing, Maine) River Run is a recently renovated 600 square ft cottage 75 ft off the St George river. It sits on 260 feet of privately owned tidal salt water river frontage just miles upriver from the Atlantic Ocean. Great for a romantic get away or to reconnect and recharge. Spend your time on the shore or sight seeing in the near by towns of Rockland and Camden

Top Guest favourite
The cottage, a contemporary black structure, is nestled within lush green fields and surrounded by trees. A gravel parking area is visible to the right, with a vehicle parked nearby. A cozy outdoor seating area can be seen in front of the cottage.
Cottage in Owls Head
4.98 out of 5 average rating, 175 reviews

Coastal Maine contemporary cottage

Our cottage is meant to be both contemporary and rustic. It is where we go to get away from the hustle and bustle of the modern world and slow down. There is no TV or internet, even our phone is an old rotary one. You will see that we have a good radio, and games and books to read, and plenty of things to do outside. We hope you will take the time at our cottage to comfortably reconnect with yourself, and each other, while enjoying what Maine is renowned for, our quality of life.

Top Guest favourite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland
4.98 out of 5 average rating, 484 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

Top Guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 115 reviews

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Top Guest favourite
The exterior of the house features a charming gray shingle facade with white trim, complemented by blooming purple azalea bushes. A neatly paved driveway leads to the entrance, while green grass surrounds the base of the structure and tall evergreen trees provide a natural backdrop.
Home in Rockport
4.96 out of 5 average rating, 112 reviews

Seaside House/Upstairs

Enjoy everything coastal Maine has to offer with this as your home base. The views are outstanding and the house is well appointed and well maintained. This house encompasses the second and third floors, with great ocean views. The first floor is a separate apartment. The property has a large back yard to relax or play in and a dedicated BBQ. The house sits across the street from Clam Cove and is not directly on the beach. Beach access is private, quick and easy.

Top Guest favourite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 202 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Guest favourite
A winter landscape features a wide expanse of untouched snow leading to a serene bay. Snow-covered homes dot the shoreline, and trees line the background against a clear blue sky, providing a peaceful view of the water.
Home in Owls Head
4.91 out of 5 average rating, 230 reviews

Island View

This conveniently located home is 1.5 miles from downtown Rockland and all the local festivals. It is a short drive to Camden & Thomaston and only minutes to the Farnsworth Art Museum & Transportation Museum . Centrally located, about 1.5 hours from both Portland and Bangor and only 2 hours from Acadia National Park. Local amenities include, beaches, scenic hiking trails, light houses, lakes, golf, skiing, art galleries, and of course lobsters.

Top Guest favourite
The exterior of the home is featured, showcasing a single-story structure with a light grey façade. A brick pathway leads to the front entrance, accompanied by well-maintained lawns and decorative flower beds. Surrounding trees provide a natural setting, enhancing the peaceful atmosphere.
Home in Rockport
4.95 out of 5 average rating, 355 reviews

Sweet home away (pet friendly)

Single floor living at its finest. Conveniently located to both Camden and Rockland, enjoy this 3 bdrm 1.5 bath home in a great country setting. Just 1/2 mile to route 1 and very close to the ocean. Come enjoy the large back deck over looking the peaceful maine woods. The front door in about 50’ from the road, which can be busy at certain time of the day. There is 1 ring doorbell for everyone’s security outside the front door of the house.

Top Guest favourite
The front of the home features a charming covered porch with red chairs and hanging flower baskets. A light-colored door with glass paneling is centered between two windows. A well-maintained lawn and a slight stone pathway enhance the inviting entrance.
Apartment in Owls Head
4.97 out of 5 average rating, 175 reviews

Coastal Vintage Living

This is a spacious 1000 sq. ft. apartment in my childhood home that has been renovated in Spring 2020 with a modern coastal theme and well appointed with vintage items. We have a well stocked kitchen, cozy dining/living room with a 43" Roku TV, and full laundry. Try a pastry from the professional baker across the road, take a walk down the street to Crockett's Beach, or go for a stroll in downtown Rockland. Remote check-in available.

Guest favourite
An open living space features light wooden walls and ceilings, creating a bright atmosphere. A sofa bed is positioned beside a wooden coffee table, while a dining table with four chairs is nearby. Windows allow natural light and offer views of the landscape outside.
Cottage in Owls Head
4.95 out of 5 average rating, 109 reviews

Owl Glass Cottage

Breathtaking oceanfront private cottage. Hinged staircase to second floor sleeping loft. French doors open to wrap-around patio and lawn that slopes to Ocean. 180 degrees of views. Perfect spot for relaxing or having a campfire in the evening. Enjoy your morning tea or coffee watching lobster and sailboats or kayakers explore and wander.

Popular amenities for Owls Head holiday rentals

When is the best time to visit Owls Head?

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Avg. price$281 NZD$300 NZD$274 NZD$284 NZD$332 NZD$403 NZD$482 NZD$482 NZD$440 NZD$363 NZD$336 NZD$334 NZD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Owls Head?

    Four-legged friends are welcome in Owls Head. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Owls Head?

    Yes! Work meets play with ease at over 40 vacation rentals in Owls Head featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly cottage rentals in Owls Head?

    Owls Head has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Owls Head?

    Experience the best of Owls Head with our cottage rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Owls Head have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Owls Head. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Owls Head have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Owls Head. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Owls Head have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Owls Head. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Owls Head?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 20 homes with a bbq area, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Owls Head

  • Total holiday rentals

    Explore 110 holiday rentals in Owls Head

  • Nightly prices starting at

    Owls Head holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Owls Head holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Owls Head rentals

  • 4.8 Average rating

    Owls Head stays are highly rated by guests—averaging 4.8 out of 5!

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