Book Holiday Homes in Pleasant Point

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Featured Holiday Homes in Pleasant Point

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Well-located, dog-friendly home - walk to footbridge & Barrett Park

Well-located, dog-friendly home - walk to footbridge & Barrett Park

Boothbay Harbor
When you a stay at this vacation home in Boothbay Harbor, you'll be by the sea, just steps from Linekin Bay and Fisherman's Memorial Park.
Well-located, dog-friendly home - walk to footbridge & Barrett Park
Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town

Wiscasset
Located in Wiscasset, this vacation home is by the sea, within a 10-minute drive of Lincoln County Jail Museum and Wiscasset Historic District.
Peaceful home with forest views & great yard - minutes to town
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Sunny coastal retreat with deck, grill, beach, dock, & ocean access

Sunny coastal retreat with deck, grill, beach, dock, & ocean access

East Boothbay
When you stay at this vacation home in East Boothbay, you'll be by the sea, within a 5-minute drive of Linekin Bay and Carousel Music Theater.
Sunny coastal retreat with deck, grill, beach, dock, & ocean access
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

Bristol
When you stay at this vacation home in New Harbor, you'll be by the sea, within a 5-minute drive of Pemaquid Point Lighthouse Park and Pemaquid Craft Co-op.
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2 out of 5
South Thomaston
Located in South Thomaston, this vacation home is by the ocean, within a 10-minute drive of General Henry Knox Museum and Maine State Prison Store.
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Thomaston
With a stay at this vacation home in Thomaston, you'll be within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Tenants Harbor
Located in Tenants Harbor, this vacation home is by the ocean, within a 15-minute drive of Tenants Harbor Marina and Marshall Point Lighthouse.
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
More then a Motel With Garden , Renovated Rooms at heart of Boothbay

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2 out of 5
Boothbay
The price is AU$703 per night from 5 Aug to 6 Aug
AU$703
5 Aug - 6 Aug
includes taxes & fees
With a stay at this vacation home in Boothbay, you'll be a 3-minute walk from Boothbay Railway Village and 7 minutes by foot from Dolphin Mini Golf.
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
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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
501 Holiday Homes
Lowest Price
AU$235
Highest Price
AU$703
Popular accommodation
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Well-located, dog-friendly home - walk to footbridge & Barrett Park, Peaceful home with forest views & great yard - minutes to town, Sunny coastal retreat with deck, grill, beach, dock, & ocean access, Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views, Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm, Brand New! Fire Pit & Grill, Movie Room, Workspace, A/C, Pets, Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D, More then a Motel With Garden , Renovated Rooms at heart of Boothbay

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$335 per night from 2 Sept to 3 Sept
AU$335
2 Sept - 3 Sept
includes taxes & fees
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
The price is AU$235 per night from 5 Aug to 6 Aug
AU$235
5 Aug - 6 Aug
includes taxes & fees
A stay at Harborline Hotel places you in the heart of Rockland, steps from Maine Lighthouse Museum and Buoy Park.
Harborline Hotel
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is AU$264 per night from 14 Aug to 15 Aug
AU$264
14 Aug - 15 Aug
includes taxes & fees
With a stay at Flagship Inn and Suites in Boothbay Harbor, you'll be a 1-minute walk from Carousel Music Theater and 6 minutes by foot from Boothbay Region Land ...
Flagship Inn and Suites
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Ledges by the Bay

Ledges by the Bay

2.5 out of 5
930 Commercial St, Rockport, ME
The price is AU$273 per night from 10 Aug to 11 Aug
AU$273
10 Aug - 11 Aug
includes taxes & fees
Located in Rockport, Ledges by the Bay is by the ocean, a 5-minute drive from Strand Theater and 8 minutes from Camden Public Library.
Ledges by the Bay
Don't see what you're looking for?
See all available properties in Pleasant Point
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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.