Holiday rentals in Owls Head

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Top-rated holiday rentals in Owls Head

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Flat 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

Guest favourite
The exterior of the cottage features a light gray shingle facade, complemented by white trim around the windows and front door. A set of three windows with flower boxes is situated on each side of the door. A welcoming porch leads to the entrance.
Home in Rockland
4.94 out of 5 average rating, 416 reviews

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

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.
Guest house 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, 176 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
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, 113 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, 203 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.

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, 441 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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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, 232 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
4.96 out of 5 average rating, 359 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.
Flat in Owls Head
4.97 out of 5 average rating, 178 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.

Top guest favourite
Tiny home in Freeport
4.99 out of 5 average rating, 371 reviews

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

Popular amenities for Owls Head holiday rentals

When is the best time to visit Owls Head?

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Avg. price£131£133£135£124£145£175£209£209£192£158£146£145
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Owls Head?

    Owls Head has cottage rentals near the water, cozy homes nestled in wooded areas, and family-friendly properties around the harbor. Many travelers choose stays with ocean views for a quieter experience.

  • What are the best things to do in Owls Head with kids?

    Kids can run on sandy beaches, spot wildlife in Owls Head State Park, or enjoy interactive exhibits at maritime and transportation museums. Picnics beside the lighthouse and gentle paddleboard sessions in calm waters are also family favorites.

  • What are some of the best things to do in Owls Head?

    You can explore Owls Head Lighthouse, walk scenic forest trails in Owls Head State Park, or learn about maritime history at museums. Watching boats in the harbor and sampling fresh seafood are often recommended by visitors.

  • How is the weather in Owls Head?

    Owls Head has snowy, cold winters around 12–37°F (-11–3°C) and mild, pleasant summers near 59–79°F (15–26°C). Spring and fall tend to be cool and damp, so packing a warm layer and waterproof outerwear is wise for most visits.

  • When is the best time to visit Owls Head?

    Late spring through early fall is often recommended for Owls Head, when weather is milder near 53–79°F (12–26°C) and local events are most active. Cooler seasons have fewer crowds and a quieter coastal atmosphere.

  • What are the best places to visit in Owls Head?

    Frequently suggested spots include Owls Head Lighthouse, Owls Head State Park, and local maritime museums. The working waterfront and nearby beaches are also popular for relaxed exploration.

  • What are some hiking trails in Owls Head?

    Owls Head State Park is known for coastal forest trails and paths that lead to scenic overlooks of Penobscot Bay. Gentle trails near the lighthouse and through shaded woods make hiking accessible for a range of abilities.

  • What are some family activities we can do in Owls Head?

    Families can explore the Maine Lighthouse Museum, walk sandy beaches, or visit Owls Head State Park for picnics and hiking. Interactive exhibits at local maritime museums and gentle kayaking in protected bays are also frequently suggested.

  • What are some of the best day trip ideas from Owls Head?

    You might explore the art galleries and working waterfront in Rockland, visit harborside towns like Camden, or hike along forested trails in nearby state parks. The region also has small craft markets, historic sites, and wildlife viewing opportunities.

  • Are there any pet friendly accommodations available in Owls Head?

    Many properties in Owls Head are pet friendly, welcoming dogs with prior arrangement. Look for homes with yards, easy beach access, or nearby walking trails for a comfortable stay with your pet.

  • What are some local tips for visiting Owls Head?

    Bring cash for farm stands and small local shops, and arrive early at popular sites for quieter experiences. Sunrise at the lighthouse and sunset walks along the beach are often suggested by locals.

  • What is Owls Head known for?

    Owls Head is known for its classic lighthouse, rocky coastal scenery, and maritime history. Many people come to explore peaceful beaches, maritime museums, and the region’s traditional seafood culture.

  • What are the best hidden gems to explore in Owls Head?

    Owls Head has peaceful coves with tide pools, small art galleries featuring local artists, and unmarked forest trails for quiet walks. The village bakery is often mentioned for its welcoming atmosphere and fresh pastries.

  • What are the best foods to try in Owls Head?

    Owls Head is known for seafood like lobster rolls, clam chowder, and baked haddock, reflecting Maine's coastal traditions. You will also find local berry pies and fresh-baked sweets at seasonal markets and bakeries.

  • What should I bring for a trip to Owls Head?

    Pack layers for varied weather, a rain jacket, and sturdy shoes for exploring rocky shorelines or forest trails. Bring swimwear, sunscreen, and a hat if you plan on outdoor activities near the water.

  • What is the nightlife in Owls Head like?

    Owls Head has a relaxed nightlife scene with casual taverns, waterfront cafés, and friendly local eateries. Many people enjoy evening walks by the harbor or listening to live acoustic music in low-key venues around the village.

  • What are the most popular events or festivals in Owls Head?

    Local festivals often celebrate maritime heritage, classic cars, and lighthouse history, especially during summer and fall weekends. Seasonal art fairs and farmers’ markets are also highlights for many visitors.

  • Are there family friendly vacation rentals in Owls Head?

    Owls Head has vacation rentals suited to families, including homes with equipped kitchens, outdoor spaces, and access to beaches or parks. Many options accommodate children and groups of various sizes.

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 £60 per night before taxes and fees

  • Verified guest reviews

    Over 5,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    100 of Owls Head holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Owls Head stays are highly rated by guests – averaging 4.9 out of 5!

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