Vacation rentals in Owls Head

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Top-rated vacation rentals in Owls Head

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Guest favourite

Guest suite in Thomaston

4.86 out of 5 average rating, 111 reviews

Private Top Floor Waterfront Apartment

Welcome to Gabriel's Anchor! 10 min walk to Main St, 10 min drive to Rockland, 2 min walk to public overlook, across the street from the lively Slipway Restaurant, on the waterfront. Gabriel's Anchor is great for couples, families, and solo adventurers looking to stay in the heart of the wonderful coastal Thomaston, Maine. 2 bdrm/1bath. 1 king bed & 1 double. kitchenette has a stovetop, fridge (no freezer, but feel free to use ours if needed), cooking utensils, dishes, coffee maker & coffee.

May 15 – 22

$145 CAD per night

Guest favourite

Guesthouse in Lincolnville

4.97 out of 5 average rating, 328 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

Oct. 17 – 24

$210 CAD per night

Guest favourite

Cottage in Owls Head

4.99 out of 5 average rating, 139 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

Oct. 6 – 13

$222 CAD per night

Guest favourite

Apartment in Rockport

4.94 out of 5 average rating, 193 reviews

Centrally Located Apartment! Rockport, Maine

GREAT LOCATION BETWEEN CAMDEN AND ROCKLAND. Walking distance (.5 mile) to Rockport Harbor and restaurants. 5 minutes driving distance from downtown shops and the harbor in Camden. 10 minutes driving distance to Rockland for art galleries, shops and the Lobster Festival in August. Walking trails, kayak rentals and Camden Hills State Park are all close by. Camden Snow Bowl ski area is 3 miles away. Sorry, no pets. Much more to do and see from this central location!

Apr. 17 – 24

$213 CAD per night

Guest favourite

Guesthouse in Rockland

4.88 out of 5 average rating, 315 reviews

Sweet Willow Suite, Rockland, private 1st floor

1-bdrm apartment in stand alone building. Light-filled open area, queen bed, full bath with walk-in shower. Located on a quiet street 1.5 blocks from Main St., restaurants & pubs, thriving arts community, and bus and ferry terminals. Suite includes many safety features. Host is hands-on, will greet you at check-in, then respect your privacy. If you are looking for a totally anonymous experience, this is not it. Licensed with the City of Rockland #STR24-7.

May 15 – 22

$176 CAD per night

Guest favourite

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

A designer’s stunning retreat just a short walk to Rockport harbor. This newly renovated 1920’s one bedroom cottage is tucked into a forested granite hillside with oversized windows to take in the view. Artfully furnished with a minimalist sensibility, the space has been fully winterized in order to be a year round sanctuary. A top of the line steam shower, heated bathroom floor, modern gas fire place, and pigmented plaster walls add touches of luxury.

Dec. 3 – 10

$229 CAD per night

Guest favourite

Home in Rockport

4.95 out of 5 average rating, 260 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.

Sep. 22 – 29

$255 CAD per night

Guest favourite

Apartment in Owls Head

4.97 out of 5 average rating, 130 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.

Oct. 16 – 23

$263 CAD per night

Guest favourite

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

Salty Dog Hilltop Guest Suite (permit #SDR22-18)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Dec. 9 – 16

$236 CAD per night

Guest favourite

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes gets you 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 DOGS

Oct. 12 – 19

$154 CAD per night

Guest favourite

Place to stay in Owls Head

4.98 out of 5 average rating, 162 reviews

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

Apr. 15 – 22

$223 CAD per night

Guest favourite

Apartment in Rockland

4.96 out of 5 average rating, 100 reviews

Mountain to Sea Serenity

Our place is a light and airy spacious studio with expansive views of both the ocean and mountains! Close to Rockland and Camden Downtown and Owls Head Airport. It offers rustic elegance and serenity. Good for couples, solo adventurers, and business travelers.

Nov. 10 – 17

$256 CAD per night