Owls Head holiday rentals

We found 389 holiday rentals — enter your dates for availability
Select from 42 homes, 13 cottages and other holiday rentals in Owls Head to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Owls Head

Showing deals for:11 Dec - 18 Dec

Living Room
Upper Deck
Kitchen
Living Room View
Exceptional
(58 reviews)

Windows on the Ocean : Penobscot Bay Contemporary

Rockport

8% off
S$6,276
for 7 nights, 1 home
S$897 per night
includes taxes & fees
Windows on the Ocean : Penobscot Bay Contemporary
Enclosed porch is so welcoming
Enjoy some quiet time in the enclosed screen porch
Farm Table was crafted from the original barn wood on the property
Back yard and porch
Exceptional
(23 reviews)

In-Village, Air Cond. Cozy Renovated 1920s Classic

Camden

7% off
S$4,477
for 7 nights, 1 home
S$640 per night
includes taxes & fees
In-Village, Air Cond. Cozy Renovated 1920s Classic
Private kitchen
The deck off the great room
kitchen as viewed from the great room
Steps leading to the water. Located at the NE corner of the property.
Exceptional
(23 reviews)

She sells seashells by the seashore.

South Thomaston

8% off
S$9,168
for 7 nights, 1 home
S$1,310 per night
includes taxes & fees
She sells seashells by the seashore.
Interior
Interior
Living area
Private kitchen
Wonderful
(9 reviews)

Harbor View from Every Room & Balcony 2 min from beach

Rockport

7% off
S$2,917
for 7 nights, 1 cottage
S$417 per night
includes taxes & fees
Harbor View from Every Room & Balcony 2 min from beach
Living room
Terrace/patio
Private kitchen
Dining
Exceptional
(32 reviews)

Historic 1820s Farmhouse Near Camden Harbor • Pet-Friendly Coastal Stay

Camden

8% off
S$1,831
for 7 nights, 1 home
S$262 per night
includes taxes & fees
Historic 1820s Farmhouse Near Camden Harbor • Pet-Friendly Coastal Stay
Living area
Property grounds
Interior
Exterior
Exceptional
(13 reviews)

Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.

Spruce Head

8% off
S$3,494
for 7 nights, 1 home
S$499 per night
includes taxes & fees
Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.
1st Floor Main Queen Bedroom
Front of the house (Fall)
Main Living Room with 55" Smart TV, Couch, Two Armchairs.
Kitchen and Dining view from the Living Room
Exceptional
(24 reviews)

Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities

South Thomaston

14% off
S$2,046
for 7 nights, 1 home
S$292 per night
includes taxes & fees
Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities
Your home in Maine
Camden Harbor; 2.5 miles away
Looking from the kitchen to the Living Room
Looking from the dining table back into the kitchen
Exceptional
(10 reviews)

Simply perfect home for Maine adventure; equally close to the harbor & the lake

Camden

8% off
S$4,211
for 7 nights, 1 home
S$602 per night
includes taxes & fees
Simply perfect home for Maine adventure; equally close to the harbor & the lake
Marina
Marina
Interior
Living room overlooking town . Note: We sit behind the Marina not ocean front .
Wonderful
(87 reviews)

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Camden

7% off
S$5,518
for 7 nights, 1 home
S$788 per night
includes taxes & fees
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Terrace/patio
Exterior
Living area
Living area
Exceptional
(38 reviews)

20%OFF Townhouse Cottage Oceanfront Complex Adj. Samoset Golf Resort+Lighthouse

Rockport

7% off
S$3,641
for 7 nights, 1 home
S$520 per night
includes taxes & fees
20%OFF Townhouse Cottage Oceanfront Complex Adj. Samoset Golf Resort+Lighthouse
Interior
Marina
Private kitchen
Living area
Exceptional
(11 reviews)

Charming recently renovated 3 bedroom 2 and 1/2 bath farmhouse

Camden

7% off
S$4,159
for 7 nights, 1 home
S$594 per night
includes taxes & fees
Charming recently renovated 3 bedroom 2 and 1/2 bath farmhouse
Lower level entry and open closet
Kitchen on main level
Interior
Back deck off living room
Exceptional
(14 reviews)

Charming 3-bedroom house with AC and WiFi in Thomaston

Thomaston

7% off
S$3,295
for 7 nights, 1 home
S$471 per night
includes taxes & fees
Charming 3-bedroom house with AC and WiFi in Thomaston

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the oceanfront setting in Owls Head

Enjoy the area's museums, history and wineries with a rental holiday home in Owls Head. Well known for its seaside, cycling and snowmobile riding, this romantic city won't disappoint. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Owls Head

Are you hoping to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Owls Head a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Owls Head State Park (0.7 mi / 1.2 km)
  • Samoset Resort Golf Course (2.9 mi / 4.7 km)
  • Cellardoor Winery (13.2 mi / 21.2 km)
  • Maine State Prison Store (6.7 mi / 10.7 km)
  • Savage Oakes Vineyard and Winery (13.8 mi / 22.2 km)
  • Morse's Sauerkraut (18.2 mi / 29.2 km)

Exploring the natural features in Owls Head

Whether you're looking for adventure or just want to take in the scenery, Owls Head is a great spot to appreciate mother nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Sandy Beach (2.6 mi / 4.2 km)
  • Rockland Harbor Park (2.8 mi / 4.6 km)
  • Rockport Marine Park (7.2 mi / 11.6 km)
  • Camden Harbor Park and Amphitheatre (8.9 mi / 14.3 km)
  • Mount Battie (9.1 mi / 14.6 km)
  • Barrett's Cove Public Beach (11.4 mi / 18.3 km)

Transport options to and around Owls Head

Fly into Rockland, ME (RKD-Knox County Regional), the closest airport, located 2.3 mi (3.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Wiscasset, ME (ISS), which is 33.6 mi (54 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Owls Head?
Houses are the most popular style of holiday rental in Owls Head, according to our data. Even if you have something a little different in mind, Vrbo has properties in a variety of sizes and shapes. Browse our options to find your perfect Owls Head pad.
How much does it cost to rent a holiday rental in Owls Head?
Length of stay, property type and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find the ultimate escape. From comfy cottages to expansive villas, all Vrbo holiday rentals provide amazing value.
How much does it cost to rent a beach house in Owls Head?
When you travel and the style and size of the property will influence the cost of your beachside escape. Click on your Owls Head travel dates to view your available options on Vrbo. Can't live without a hot tub? Use the filters to choose the features and amenities you need.
Are there pet-friendly holiday rentals in Owls Head?
Pack a suitcase for your beloved pooch because Owls Head has 45 holiday homes that throw open their doors to pets. Let your furriest friend enjoy fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Owls Head?
Add an extra layer of fun to your getaway by booking your family into one of the two houses with a private pool in Owls Head. Use our search filter to find properties with pools on Vrbo, then spend your days splashing and playing in a swimming pool that's exclusively for you.
What are popular rental amenities in Owls Head?
Some of the most popular rental amenities people prefer in Owls Head are tennis, a nearby waterfront and mountain views. Whether you're hitting the road with your besties, family or even pets, Vrbo holiday rentals include the best amenities for hanging out with your loved ones.
Are there large group holiday rentals in Owls Head?
Owls Head has three holiday rentals that can fit 10 or more guests. These properties come with the space you need to enjoy good times with family and friends.
Are there holiday rentals in Owls Head that welcome kids?
Bring the whole family together for a fun-packed adventure in Owls Head at one of our 45 family-friendly holiday rentals. Many of these stays feature conveniences that are just perfect for trips with youngsters, such as full kitchens, living rooms and outdoor spaces. Just click on the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Owls Head?
Keeping the kids entertained during your stay in Owls Head is a snap with these leading family-friendly attractions:
  • Sandy Beach
  • Laite Memorial Beach
  • Owls Head Transportation Museum
Are there one-bedroom holiday rentals in Owls Head?
Owls Head has six one-bedroom rentals available. Often situated in prime spots because of their compact size, a one-bedroom holiday rental is perfect if you're getting away with a friend or your partner. And with home comforts like kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this fantastic destination.
Can I find two-bedroom holiday rentals in Owls Head?
Gather your loved ones and relax in total privacy and comfort in one of the five two-bedroom holiday properties Owls Head has to offer.
Are there holiday rentals with WiFi in Owls Head?
Owls Head has 17 holiday rentals with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to posting pics on social media, these Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in Owls Head?
You'll have your pick of 16 holiday rentals with air conditioning in Owls Head offering that gentle, cool breeze and extra bit of comfort. Just enter your preferred dates of travel and then use our filters to find stays with air conditioning.
How old do you have to be to rent a holiday rental in Owls Head?
The minimum age is normally 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your chosen Owls Head holiday rental before making a booking.
How long can I rent a holiday rental in Owls Head for?
The amount of time you can rent an Owls Head holiday rental for is down to the property. Just put in your dates of travel to view options that offer long-term stays. They feature all you require to make your extended holiday more convenient and enjoyable, like air conditioning and laundries. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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