Book Holiday Homes in Pleasant Point

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Featured Holiday Homes in Pleasant Point

Admiral's Quarters - Room 12

Admiral's Quarters - Room 12

Boothbay Harbor
The price is AU$736 per night from 18 Nov to 19 Nov
AU$736
includes taxes & fees
18 Nov - 19 Nov
When you a stay at this vacation home in Boothbay Harbor, you'll be by the ocean, within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor ...
Admiral's Quarters - Room 12
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute walk of Boothbay Region Land Trust and Boothbay Region Historical ...
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Rockport
When you stay at this vacation home in Rockport, you'll be on the beach, within a 5-minute drive of Oakland Park Bowling Lanes and Owls Head Lighthouse.
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
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Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is AU$553 per night from 1 Dec to 2 Dec
AU$553
includes taxes & fees
1 Dec - 2 Dec
When you stay at this vacation home in Owls Head, you'll be by the sea, within a 5-minute drive of Breakwater Vineyards and Coastal Children's Museum.
Comfortable, Close to Town Home, with Oceanview.
Waterfront home with beautiful bay views - near shops & dining

Waterfront home with beautiful bay views - near shops & dining

Owls Head
Located in Owls Head, this vacation home is by the ocean, within a 15-minute walk of Sail Power and Steam Museum and Snow Marine Park.
Waterfront home with beautiful bay views - near shops & dining
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
The price is AU$478 per night from 18 Nov to 19 Nov
AU$478
includes taxes & fees
18 Nov - 19 Nov
Located in Thomaston, this vacation home is within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
2 Bedroom Close to Town Home
Tranquil waterfront near Rockland, Camden-family and dog friendly

Tranquil waterfront near Rockland, Camden-family and dog friendly

South Thomaston
With a stay at this vacation home, you'll be centrally located in South Thomaston, within a 10-minute drive of Breakwater Vineyards and Owls Head Transportation ...
Tranquil waterfront near Rockland, Camden-family and dog friendly
Quintessential Maine Oceanfront home

Quintessential Maine Oceanfront home

Bremen
When you stay at this vacation home in Bremen, you'll be on the beach and 10 minutes by car from Penobscot Marine Museum.
Quintessential Maine Oceanfront home
Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays

Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays

Rockport
A stay at this vacation home places you in the heart of Rockport, within a 15-minute walk of Rockport Marine Park and Andre the Seal Statue.
Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pleasant Point Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pleasant Point vacation homes are the perfect way for you to wing it.

Holiday houses in Pleasant Point let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pleasant Point in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pleasant Point adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pleasant Point with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pleasant Point vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pleasant Point Holiday Homes essential information

Accommodation
356 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$736
Popular accommodation
Admiral's Quarters - Room 12, Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views , Comfortable, Close to Town Home, with Oceanview., Waterfront home with beautiful bay views - near shops & dining, 2 Bedroom Close to Town Home, Tranquil waterfront near Rockland, Camden-family and dog friendly, Quintessential Maine Oceanfront home, Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays

Top trending hotels in Pleasant Point

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 18 Nov to 19 Nov
AU$201
includes taxes & fees
18 Nov - 19 Nov
When you stay at The Country Inn at Camden Rockport in Rockport, you'll be near the beach, just steps from Golfer's Crossing Mini Golf and 9 minutes by foot ...
The Country Inn at Camden Rockport
Rockland Harbor Hotel

Rockland Harbor Hotel

2.5 out of 5
520 Main Street, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 1 Dec to 2 Dec
AU$272
includes taxes & fees
1 Dec - 2 Dec
A stay at Rockland Harbor Hotel places you in the heart of Rockland, steps from Rockland Ferry Terminal and 3 minutes by foot from Strand Theater.
Rockland Harbor Hotel
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$236 per night from 18 Nov to 19 Nov
AU$236
includes taxes & fees
18 Nov - 19 Nov
With a stay at Tugboat Inn in Boothbay Harbor, you'll be within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor Marina.
Tugboat Inn
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Trade Winds on the Bay

Trade Winds on the Bay

3 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 23 Nov to 24 Nov
AU$216
includes taxes & fees
23 Nov - 24 Nov
A stay at Trade Winds on the Bay places you in the heart of Rockland, steps from Maine Lighthouse Museum and Project Puffin Visitor Center.
Trade Winds on the Bay
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.