Book Holiday Homes in Pleasant Point

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Featured Holiday Homes in Pleasant Point

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 home on 6 acres with multi-level deck & spectacular view

Oceanfront home on 6 acres with multi-level deck & spectacular view

Rockport
Located in Rockport, this vacation home is by the ocean, within a 5-minute drive of Beech Hill Preserve and Oakland Park Bowling Lanes.
Oceanfront home on 6 acres with multi-level deck & spectacular view
Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Boothbay
With a stay at this vacation home, you'll be centrally located in East Boothbay, just a 3-minute walk from Grimes Cove Beach and 13 minutes by foot from Linekin ...
Oceanfront home & guesthouse w/ incredible ocean views, deck & location
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The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

Saint George
Located in Tenants Harbor, this vacation home is within a 15-minute drive of Tenants Harbor Marina and Marshall Point Lighthouse.
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Single-family home situated on the waterfront in the beautiful midcoast Maine

Single-family home situated on the waterfront in the beautiful midcoast Maine

Bristol
With a stay at this vacation home in New Harbor (Pemaquid Beach), you'll be a 3-minute walk from Colonial Pemaquid State Historic Site and within a 5-minute ...
Single-family home situated on the waterfront in the beautiful midcoast Maine
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
Spectacular Oceanfront Home - MidCoast Maine [EV Charger]

Spectacular Oceanfront Home - MidCoast Maine [EV Charger]

Camden/Friendship
With a stay at this vacation home in Friendship, you'll be on the beach, and 10.5 mi (16.9 km) from St. George River and 12 mi (19.3 km) from Maine State Prison ...
Spectacular Oceanfront Home - MidCoast Maine [EV Charger]
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be on the waterfront, just a 3-minute walk from Opera House at Boothbay Harbor and 5 minutes by ...
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is AU$568 per night from 2 Feb to 3 Feb
AU$568
includes taxes & fees
2 Feb - 3 Feb
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.
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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
351 Holiday Homes
Lowest Price
AU$164
Highest Price
AU$568
Popular accommodation
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Oceanfront home on 6 acres with multi-level deck & spectacular view, Oceanfront home & guesthouse w/ incredible ocean views, deck & location, The Perch - A cozy cottage minutes from Tenants Harbor, with water access!, Single-family home situated on the waterfront in the beautiful midcoast Maine, Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views , Spectacular Oceanfront Home - MidCoast Maine [EV Charger], The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock, Comfortable, Close to Town Home, with Oceanview.

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$208 per night from 11 Feb to 12 Feb
AU$208
includes taxes & fees
11 Feb - 12 Feb
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
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 13 Feb to 14 Feb
AU$164
includes taxes & fees
13 Feb - 14 Feb
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
Hampton Inn & Suites Rockland

Hampton Inn & Suites Rockland

2.5 out of 5
190 New County Rd, Thomaston, ME
Fully refundableReserve now, pay when you stay
The price is AU$236 per night from 9 Feb to 10 Feb
AU$236
includes taxes & fees
9 Feb - 10 Feb
When you stay at Hampton Inn & Suites Rockland in Thomaston, you'll be near the airport, within a 5-minute drive of Rockland Harbor Park and Maine Lighthouse ...
Hampton Inn & Suites Rockland
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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
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.