Owls Head vacation rentals

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Top-rated vacation rentals in Owls Head

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

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Guest favorite

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 14 – 21

$81 per night

Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 353 reviews

ONE BIG ROOM Studio in Rockport

Roomy and cozy, the Studio has high ceilings, winter water views, hard wood floors,, VERY comfortable king size bed, kitchenette, pull out love seat and super comfy lazy boy chair. Also has private bath, private entrance and parking. A short walk to lovely Rockport Harbor beach and park, and town, Rockport Opera House, Maine Media, Camden is 5 minute drive, 15 mins to Rockland, very convenient location to see all that midcoast Maine has to offer, plus a special, romantic getaway for you!

Feb 10 – 17

$123 per night

Guest favorite

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

Apr 4 – 11

$121 per night

Guest favorite

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!

Mar 19 – 26

$115 per night

Guest favorite

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 18 – 25

$95 per night

Guest favorite

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.

Mar 24 – 31

$132 per night

Guest favorite

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 23 – 30

$150 per night

Guest favorite

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

$144 per night

Guest favorite

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.

Nov 9 – 16

$131 per night

Guest favorite

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 7 – 14

$86 per night

Guest favorite

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.

Nov 19 – 26

$125 per night

Guest favorite

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 26 – Dec 3

$142 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Owls Head vacation rentals

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Owls Head's top sights

Harbor Park5 locals recommend

Maine Lobster Festival13 locals recommend

Owls Head Lighthouse73 locals recommend

Maine Lighthouse Museum22 locals recommend

Archer’s on the Pier41 locals recommend

Owls Head Transportation Museum70 locals recommend

Other great vacation rentals in Owls Head

Guest favorite

Cottage in Lincolnville

4.91 out of 5 average rating, 331 reviews

Eco-friendly studio - ocean views, close to beach

Nov 1 – 8

$114 per night

Guest favorite

Home in Owls Head

4.94 out of 5 average rating, 186 reviews

Comfortable, Close to Town Home, with Oceanview.

Feb 3 – 10

$250 per night

Guest favorite

Guesthouse in Lincolnville

4.96 out of 5 average rating, 121 reviews

Cabin with beautiful ocean views

Oct 20 – 27

$148 per night

Guest favorite

Apartment in Rockland

4.97 out of 5 average rating, 192 reviews

Harbor Duet Apartment

$135 per night

Guest favorite

Guesthouse in Lincolnville

4.97 out of 5 average rating, 328 reviews

"The Lair" Guesthouse

Aug 15 – 22

$138 per night

Guest favorite

Apartment in Camden

4.99 out of 5 average rating, 110 reviews

Sunny In-Town Camden Studio, 15% weekly discount

Oct 4 – 11

$131 per night

Guest favorite

Cabin in Bremen

4.95 out of 5 average rating, 173 reviews

Ocean Front Cottage: Little Heaven

Sep 30 – Oct 7

$138 per night

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Jan 15 – 22

$134 per night

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Other great vacation rentals in Owls Head

Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 231 reviews

The perfect getaway - Camden/Rockport/Rockland

Apr 4 – 11

$125 per night

Guest favorite

Cottage in South Thomaston

4.93 out of 5 average rating, 115 reviews

Timeless Tides Cottage

Jan 29 – Feb 5

$223 per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 123 reviews

The Barn

May 4 – 11

$124 per night

Guest favorite

Apartment in Camden

4.98 out of 5 average rating, 181 reviews

Mount Battie Studio

Nov 18 – 25

$100 per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Nov 26 – Dec 3

$89 per night

Guest favorite

Place to stay in Camden

4.97 out of 5 average rating, 102 reviews

Camden Intown House. Lovely upstairs suite.

Jun 7 – 14

$129 per night

Guest favorite

Guesthouse in Camden

4.99 out of 5 average rating, 151 reviews

In-town Private Suite.

May 2 – 9

$131 per night

Guest favorite

Apartment in Belfast

4.99 out of 5 average rating, 262 reviews

Room with a Brew

Jan 8 – 15

$113 per night

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Quick stats about vacation rentals in Owls Head

Total rentals
110 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
5.4K reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Owls Head?
Yes! Work meets play with ease at over 50 vacation rentals in Owls Head featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Owls Head?
Four-legged friends are welcome in Owls Head. Choose from more than 40 vacation rentals for guests traveling with pets.
Do cottage rentals in Owls Head have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Owls Head. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Owls Head?
Experience the best of Owls Head with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Owls Head?
Owls Head has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Owls Head have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Owls Head. Enjoy a tailored experience with all the comforts you desire.

Owls Head vacation rentals

Top-rated vacation rentals in Owls Head

Vacation rentals for every style

Chalets

Houses

Hotels

Popular amenities for Owls Head vacation rentals

Stay near Owls Head's top sights

Other great vacation rentals in Owls Head

Cottage in Lincolnville

Home in Owls Head

Guesthouse in Lincolnville

Apartment in Rockland

Guesthouse in Lincolnville

Apartment in Camden

Cabin in Bremen

Guesthouse in South Bristol

Other great vacation rentals in Owls Head

Apartment in Rockport

Cottage in South Thomaston

Home in Appleton

Apartment in Camden

Guesthouse in Orland

Place to stay in Camden

Guesthouse in Camden

Apartment in Belfast

Quick stats about vacation rentals in Owls Head

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

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

Are there pet-friendly vacation rentals in Owls Head?

Do cottage rentals in Owls Head have wifi?

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

Are there family-friendly house rentals in Owls Head?

Do house rentals in Owls Head have a bbq area?

Destinations to explore