Book Holiday Homes in Pleasant Point
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Featured Holiday Homes in Pleasant Point

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
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 |
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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 |
More accommodations in Pleasant Point
Top trending hotels in Pleasant Point

The Country Inn at Camden Rockport

Harborline Hotel

Tugboat Inn

Fishermans Wharf Inn
More ways to explore Pleasant Point
Top picks
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^Subject to availability and chosen travel dates.