Book Holiday Homes in Pleasant Point

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pleasant Point

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
The price is AU$430 per night from 24 Apr to 25 Apr
AU$430
includes taxes & fees
24 Apr - 25 Apr
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
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
Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Beautifully renovated home w/ prime location - walk to the footbridge & downtown

Boothbay Harbor
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Fisherman's Memorial Park and 8 minutes by foot ...
Beautifully renovated home w/ prime location - walk to the footbridge & downtown
Save an average of 15% on thousands of hotels when you're signed in
Elegant home right in town with gorgeous water view, deck & interior

Elegant home right in town with gorgeous water view, deck & interior

Wiscasset
With a stay at this vacation home, you'll be centrally located in Wiscasset, just a 5-minute walk from Castle Tucker and 12 minutes by foot from Lincoln County ...
Elegant home right in town with gorgeous water view, deck & interior
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Rockport
Located in Rockport, this vacation home is by the ocean, within a 5-minute drive of Oakland Park Bowling Lanes and Owls Head Lighthouse.
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

Bristol
With a stay at this vacation home, you'll be centrally located in Bristol, within a 15-minute drive of Pemaquid Craft Co-op and Biscay Pond.
Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You
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
Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay
Located in Boothbay, this vacation home is in a rural location, within a 15-minute walk of The Boothbay Playhouse and Dolphin Mini Golf.
Home In Boothbay - Holiday Getaway
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

Boothbay
With a stay at this vacation home in East Boothbay (Ocean Point), you'll be a 4-minute walk from Linekin Bay and 11 minutes by foot from Grimes Cove Beach.
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Don't see what you're looking for?
See all available properties in Pleasant Point
View all properties
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
449 Holiday Homes
Lowest Price
AU$198
Highest Price
AU$430
Popular accommodation
2 Bedroom Close to Town Home, Oceanfront home on 6 acres with multi-level deck & spectacular view, Beautifully renovated home w/ prime location - walk to the footbridge & downtown, Elegant home right in town with gorgeous water view, deck & interior, Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach, Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Home In Boothbay - Holiday Getaway, Welcome to Owl House - Your Coastal Retreat in East 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$211 per night from 13 Apr to 14 Apr
AU$211
includes taxes & fees
13 Apr - 14 Apr
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

4 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 15 Apr to 16 Apr
AU$198
includes taxes & fees
15 Apr - 16 Apr
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
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$244 per night from 13 Apr to 14 Apr
AU$244
includes taxes & fees
13 Apr - 14 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$257 per night from 1 May to 2 May
AU$257
includes taxes & fees
1 May - 2 May
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
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.