Pleasant Point holiday rentals

We found 314 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Pleasant Point that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Pleasant Point

Showing deals for:18 Dec - 25 Dec

Pick your chair. While watching the Friendship Lobster Boast Races.
Sea view through wavy glass in living room.
Matching Dinning Hutch.
First Floor Queen Bedroom with an attached second bathroom.
Exceptional
(99 reviews)

Historic "Wilbur Morse" Friendship Maine Ocean Home

Friendship

17% off
AU$8,131
for 7 nights, 1 home
AU$1,162 per night
includes taxes & fees
Historic "Wilbur Morse" Friendship Maine Ocean Home
Exterior
Living Area with soaring Cathedral Ceiling
View the pond from the peaceful covered porch.
King bed with light cotton quilt in summer & down bedding for the cooler months.
Exceptional
(61 reviews)

20% Off Sept. Bookings, 3 night min., 1st flr King & Full Loft, Pets Free

Round Pond

8% off
AU$2,848
for 7 nights, 1 cottage
AU$407 per night
includes taxes & fees
20% Off Sept. Bookings, 3 night min., 1st flr King & Full Loft, Pets Free
kitchen as viewed from the great room
The deck off the great room
Living area
Private kitchen
Exceptional
(23 reviews)

She sells seashells by the seashore.

South Thomaston

9% off
AU$9,981
for 7 nights, 1 home
AU$1,426 per night
includes taxes & fees
She sells seashells by the seashore.
Newly Addition - 1st Floor King
Pemaquid Beach 10 minutes
Exterior detail
Exterior
Exceptional
(64 reviews)

Our Premier Cottage - Laundry, Large, Luxurious King Bedroom, Pets Free

Round Pond

9% off
AU$3,002
for 7 nights, 1 cottage
AU$429 per night
includes taxes & fees
Our Premier Cottage - Laundry, Large, Luxurious King Bedroom, Pets Free
Interior
Property grounds
Exterior
Property grounds
Exceptional
(14 reviews)

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

Spruce Head

8% off
AU$4,050
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.
Main Living Room with 55" Smart TV, Couch, Two Armchairs.
Front of the house (Fall)
Kitchen and Dining view from the Living Room
1st Floor Main Queen Bedroom
Exceptional
(24 reviews)

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

South Thomaston

15% off
AU$3,015
for 7 nights, 1 home
AU$431 per night
includes taxes & fees
Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities
Side of the house with the screened in porch.
Living area
Interior
Living area
Exceptional
(35 reviews)

The Round Pond Getaway. Screened Porch · Fire Pit · Walk to Harbor

Round Pond

8% off
AU$2,999
for 7 nights, 1 home
AU$428 per night
includes taxes & fees
The Round Pond Getaway. Screened Porch · Fire Pit · Walk to Harbor
Front door entry
Kitchen on main level
Lower level entry and open closet
Interior
Exceptional
(14 reviews)

Charming 3-bedroom house with AC and WiFi in Thomaston

Thomaston

8% off
AU$3,481
for 7 nights, 1 home
AU$497 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

Find the perfect holiday rental for your Pleasant Point getaway

Learn about the unique charm of Pleasant Point with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Pleasant Point

Are you hoping to discover attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Pleasant Point a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Maine State Prison Store (9.1 mi / 14.7 km)
  • Samoset Resort Golf Course (14.7 mi / 23.7 km)
  • Owls Head State Park (14.9 mi / 24 km)
  • Pemaquid Craft Co-op (12 mi / 19.4 km)

Exploring the natural landscape of Pleasant Point

Whether you're looking for fun outdoor activities or just want to take in the scenery, Pleasant Point is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • La Verna Preserve (10.2 mi / 16.4 km)
  • Sandy Beach (13.1 mi / 21 km)
  • Rockland Harbor Park (13.1 mi / 21 km)
  • Pemaquid Point Lighthouse Park (13.9 mi / 22.3 km)
  • Damariscotta Lake (17 mi / 27.3 km)
  • Biscay Pond (9.3 mi / 14.9 km)

Transport to and around Pleasant Point

Fly into Rockland, ME (RKD-Knox County Regional), the closest airport, located 11.9 mi (19.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Wiscasset, ME (ISS), which is 20.7 mi (33.3 km) away.

Frequently asked questions

What are the top attractions in Pleasant Point?
In Pleasant Point, Maine, visitors can engage in the area's rich Native American heritage, particularly through the Passamaquoddy Tribe. One of the popular attractions is the nearby Quoddy Head State Park, which features stunning coastal views, hiking trails, and the famous West Quoddy Head Lighthouse, the easternmost point in the United States. The park is great for nature enthusiasts and those interested in birdwatching.Additionally, the surrounding area offers beautiful opportunities for kayaking and exploring the local marine life. The nearby town of Eastport is also worth a visit, known for its artistic community and charming waterfront. Here, you can find local shops, galleries, and the annual Eastport Pirate Festival, which draws visitors from afar in the summer months.
Are all fees included in the Pleasant Point holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pleasant Point holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pleasant Point 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 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.
Are there any discounts for Pleasant Point holiday homes?
You can find great discounts on holiday homes in Pleasant Point on Stayz, 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.
Can I change or cancel my Pleasant Point holiday home booking on Stayz?
To find Pleasant Point holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pleasant Point?
A long-stay holiday home in Pleasant Point 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pleasant Point holiday home?
Book your Pleasant Point holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pleasant Point?
Prices for holiday homes in Pleasant Point 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pleasant Point to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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