Book Holiday Homes in Pleasant Point

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Featured Holiday Homes in Pleasant Point

Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20

Rockland
When you stay at this vacation home in Rockland, you'll be by the sea, within a 15-minute walk of Rockland Harbor Park and Maine Coastal Islands National Wildlife ...
Simplicity-Just what you need! STR24-20
Slow Down & Go Back in Time-Relax Completely in Our Maine Home

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

New Harbor
When you stay at this vacation home in New Harbor, you'll be by the sea, within a 5-minute drive of Pemaquid Craft Co-op and Rachel Carson Salt Pond ...
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be on the beach, just a 4-minute walk from Boothbay Harbor Memorial Library and 6 minutes by foot ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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Relaxed South End Rockland Bungalow, 5 minute walk from downtown

Relaxed South End Rockland Bungalow, 5 minute walk from downtown

4 out of 5
Rockland
With a stay at this vacation home in Rockland, you'll be within a 15-minute walk of Sandy Beach and Coastal Children's Museum.
Relaxed South End Rockland Bungalow, 5 minute walk from downtown
Downtown Boothbay Harbor, 2-Story Cottage

Downtown Boothbay Harbor, 2-Story Cottage

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society ...
Downtown Boothbay Harbor, 2-Story Cottage
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
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.
Charming Rockport, Maine 3BR – Walk to Picturesque Harbor & Downtown

Charming Rockport, Maine 3BR – Walk to Picturesque Harbor & Downtown

Rockport
With a stay at this vacation home in Rockport, you'll be a 3-minute walk from Rockport Marine Park and 5 minutes by foot from Andre the Seal Statue.
Charming Rockport, Maine 3BR – Walk to Picturesque Harbor & Downtown
Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, steps from Burnt Island Living Lighthouse and 4 minutes by foot from Boothbay Harbor ...
Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, steps from Linekin Bay and 12 minutes by foot from Barrett Park.
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
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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
455 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Simplicity-Just what you need! STR24-20, Slow Down & Go Back in Time-Relax Completely in Our Maine Home, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Relaxed South End Rockland Bungalow, 5 minute walk from downtown, Downtown Boothbay Harbor, 2-Story Cottage, Comfortable, Close to Town Home, with Oceanview., Charming Rockport, Maine 3BR – Walk to Picturesque Harbor & Downtown, Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle, Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

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
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
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive, Rockland, ME
Fully refundableReserve now, pay when you stay
A stay at Harborline Hotel places you in the heart of Rockland, steps from Maine Lighthouse Museum and Buoy Park.
Harborline Hotel
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
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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Fishermans Wharf Inn

Fishermans Wharf Inn

2.5 out of 5
22 Commercial St, Boothbay Harbor, ME
With a stay at Fishermans Wharf Inn, you'll be centrally located in Boothbay Harbor, steps from Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Fishermans Wharf Inn
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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.