Owls Head holiday lettings

We found 425 holiday rentals — enter your dates for availability

Select from 27 homes, 15 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:13 Feb - 20 Feb

Image gallery for 25% OFF 2025 LABOR DAY WE+AUG, SEPT, OCT Days Oceanfront Adj. Resort +Lighthouse

Exterior
10 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

25% OFF 2025 LABOR DAY WE+AUG, SEPT, OCT Days Oceanfront Adj. Resort +Lighthouse

Rockport, ME

8% off
Price is £2,141
for 7 nights, 1 home
£306 per night
includes taxes & fees
25% OFF 2025 LABOR DAY WE+AUG, SEPT, OCT Days Oceanfront Adj. Resort +Lighthouse

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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)
  • Maine State Prison Store (6.7 mi / 10.7 km)
  • Cellardoor Winery (13.2 mi / 21.2 km)
  • Morse's Sauerkraut (18.2 mi / 29.2 km)
  • Breakwater Vineyards (2.2 mi / 3.6 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)
  • Megunticook Lake (8.8 mi / 14.2 km)
  • Camden Harbor Park and Amphitheatre (8.9 mi / 14.3 km)
  • Mount Battie (9.1 mi / 14.6 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 best area to stay in Owls Head when booking a holiday rental?
When considering a holiday rental in Owls Head, Maine, a popular area to stay is along the scenic coastline, particularly near the Owls Head State Park. This neighbourhood offers stunning views of the ocean and easy access to the park's beautiful trails, making it superb for nature lovers and those who enjoy outdoor activities. The park is not only a great spot for hiking but also features a picturesque lighthouse, which is a favourite among photographers and visitors alike.

Another lovely area to consider is the vicinity around the Owls Head General Store, where you'll find a charming blend of local culture and convenience. Staying near this spot allows you to enjoy delicious local fare and shop for unique Maine souvenirs. Additionally, the nearby Rockland Breakwater Lighthouse, a short drive away, is a must-see attraction, offering a scenic walk along the breakwater with rewarding views of the harbour.
How much does it cost to rent a holiday home in Owls Head?
Prices for holiday rentals in Owls Head vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Owls Head to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Owls Head holiday house rentals?
You can find great discounts on house rentals in Owls Head on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Owls Head?
For renting a beach house in Owls Head, Maine, the area around Owls Head State Park is particularly appealing. This scenic stretch of coastline offers holiday rentals with easy access to picturesque beaches and stunning views of the ocean. Many properties in this area come equipped with amenities such as outdoor decks, barbeque facilities, and fully equipped kitchens, making them ideal for families or groups wishing to enjoy a relaxing seaside holiday.

Additionally, the nearby Rockland Harbour area provides further options, with charming cottages and homes that often feature panoramic views of the water. Many of these rentals include amenities like private patios, fire pits, and direct beach access, superb for enjoying the coastal lifestyle. This area is also conveniently located near local shops, restaurants, and art galleries, adding to the overall experience for travellers.
Where are the best Owls Head ski resort rentals?
For renting ski accommodations near Owls Head, Maine, the nearby area of Rockland offers some great options. This charming coastal town is approximately a 20-minute drive from the Owls Head ski resort, making it a convenient base for winter sports enthusiasts. In Rockland, visitors can find a variety of properties, including cosy cottages and spacious family homes, many of which boast amenities such as full kitchens, fireplaces, and outdoor spaces for relaxation after a day on the slopes.

Additionally, properties in Rockport, just a bit further along the coast, provide a picturesque setting with stunning views of the water. Here, rentals often come with features like hot tubs and access to community amenities such as swimming pools and fitness centres, ideal for unwinding after skiing. The town also has a selection of local restaurants and shops, adding to the convenience for travellers.
What is the most popular type of holiday rental accomodation in Owls Head?
In Owls Head, holiday houses are the most popular type of rental, with around 35 available throughout the area. These homes often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor areas such as decks or gardens, superb for enjoying the natural surroundings after a day of exploring nearby attractions like Owls Head Lighthouse and the picturesque coastal scenery. Additionally, there are about 19 cottages, which provide a charming, rustic atmosphere with similar amenities but on a smaller scale, often appealing to couples or small families. Several apartments and cabins are also available, offering varied experiences for travellers seeking a tranquil getaway in this lovely part of Maine.
Are there any family house rentals in Owls Head?
In Owls Head, Maine, there is a substantial selection of family-friendly homes, with around 47 available for rent. This picturesque area is superb for families looking to enjoy coastal living while being close to outdoor activities. Many properties in the vicinity feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.
Can I rent a holiday home with a pool or hot tub in Owls Head?
In Owls Head, Maine, there are several holiday homes available for rent that feature pools and hot tubs, making it a lovely option for travellers seeking relaxation amidst scenic surroundings. This coastal town is known for its charming atmosphere and proximity to beautiful beaches and parks.

Many of the rentals in the area come equipped with amenities such as private pools, outdoor hot tubs, and spacious patios for enjoying the fresh air. Inside, you can expect fully equipped kitchens, comfortable living areas, and multiple bedrooms, accommodating families or groups looking for a leisurely getaway.
Can I find long-stay holiday rentals in Owls Head?
A long-stay holiday rental in Owls Head is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Owls Head?
In Owls Head, there are several pet-friendly house rentals available, offering a delightful escape for travellers with furry companions. Many of these properties feature amenities such as spacious gardens, outdoor decks, and fully equipped kitchens, ideal for families or groups looking to enjoy a relaxing holiday. Additionally, some rentals may include cosy living areas with fireplaces, great for unwinding after a day of exploration.
Are there any remote work holiday rentals in Owls Head?
In Owls Head, Maine, there is a good selection of remote work holiday rentals available, with around 52 options to choose from. Many of these properties come equipped with essential amenities for remote work, such as reliable Wi-Fi, dedicated desks, and comfortable office chairs, ensuring a productive environment. Some rentals also feature laptop workspaces and safes for added convenience and security. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Owls Head holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Owls Head with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Owls Head?
In Owls Head, popular rental amenities typically include kitchens equipped with essential appliances such as refrigerators, microwaves, and stovetops, allowing guests to prepare their own meals during their stay. Many properties also feature coffee makers, ensuring that travellers can enjoy their morning brew at their convenience. These amenities contribute to a comfortable and homely atmosphere, ideal for those looking to relax after exploring the local coastline and nearby attractions.
When is the best time to visit Owls Head for a holiday rental?
The best time to book a holiday rental in Owls Head is during the summer months, particularly in July, when the area is bustling with visitors drawn to its stunning coastal scenery and charming local attractions. This peak season, running from June to August, is ideal for those seeking outdoor adventures such as hiking, kayaking, and exploring picturesque beaches.

July, in particular, offers warm temperatures averaging around 24°C, providing a comfortable environment for sightseeing or relaxing by the shore. The lively atmosphere during this time means you'll have access to various local events, including art shows and seafood festivals that celebrate the region's rich culture and culinary delights.

If you're looking for a more budget-friendly option, consider visiting in November. While this month is quieter, it offers a unique charm with fewer crowds and stunning autumn landscapes. The crisp air and beautiful fall colours create a serene backdrop for coastal walks and exploration of the area's historic sites.
How early should I book a Owls Head holiday rental?
Book your Owls Head holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Owls Head?
In Owls Head, visitors can enjoy a selection of attractions that showcase the area's natural beauty and maritime heritage. Owls Head State Park offers stunning views of Penobscot Bay and features picturesque walking trails, making it a lovely spot for leisurely outdoor activities. The Owls Head Lighthouse, a historic site, is another must-see, providing insight into the area's maritime history and offering scenic vistas.
Can I change or cancel my Owls Head home rental booking on Vrbo?
To find Owls Head holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Owls Head holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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