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Pleasant Point Vacation Rentals

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Our top choices for Pleasant Point vacation rentals

Bee Hive Cottage, Romantic Maine Waterfront Cottag

Bee Hive Cottage, Romantic Maine Waterfront Cottag
2.0 star property
Cushing
The price is CA $769
CA $1,090 total
includes taxes & fees
Aug 2 - Aug 3
Bee Hive Cottage, Romantic Maine Waterfront Cottag

Bee Hive Cottage, romantic Maine waterfront cottag

Bee Hive Cottage, romantic Maine waterfront cottag
Cushing
10.0 out of 10, Exceptional, (1 review)
"we enjoyed sipping coffee in the morning watching the lobster boats go to/from the working harbor next door."
United States
Karen L.
The price is CA $592
CA $1,026 total
includes taxes & fees
Aug 2 - Aug 3
Bee Hive Cottage, romantic Maine waterfront cottag

Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
10.0 out of 10, Exceptional, (3 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is CA $316
CA $461 total
includes taxes & fees
Aug 15 - Aug 16
Come Spring Farm Airstream , Lake & farm animals

Damariscotta Lakefront Cottage perfect for a relaxing getaway

Damariscotta Lakefront Cottage perfect for a relaxing getaway
Jefferson
The price is CA $470
CA $1,022 total
includes taxes & fees
Aug 3 - Aug 4
Damariscotta Lakefront Cottage perfect for a relaxing getaway

Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.4 out of 10, Very good, (6 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is CA $176
CA $271 total
includes taxes & fees
Jul 23 - Jul 24
Newly Renovated Cozy Cove Cabin at White Anchor Inn

Across the road from Pemaquid Beach — wooded king-bed cabin

Across the road from Pemaquid Beach — wooded king-bed cabin
Pemaquid Beach
10.0 out of 10, Exceptional, (19 reviews)
"Great little place. Loved the area."
United States
Rob S.
The price is CA $301
CA $514 total
includes taxes & fees
Jul 19 - Jul 20
Across the road from Pemaquid Beach — wooded king-bed cabin

Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (64 reviews)
"Perfect home away from home. Very well stocked kitchen, the beds were very comfy and everything was just overall cozy. Such a serene location. We will definitely stay again next time we come to visit our grandkids. "
United States
Tina B.
The price is CA $253
CA $796 total
includes taxes & fees
Jul 23 - Jul 24
Oceanview Bungalow Style Home in Owls Head

Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great experience, great location! Would highly recommend."
United States
Lynn R.
The price is CA $156
CA $348 total
includes taxes & fees
Jul 22 - Jul 23
Cheerful Cottage Close to Everything 12

Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (25 reviews)
"Very clean and allows for easy access around the area! "
United States
Sarah V.
The price is CA $171
CA $252 total
includes taxes & fees
Jul 21 - Jul 22
Simplicity-Just what you need! STR24-20

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (6 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is CA $270
CA $507 total
includes taxes & fees
Jul 19 - Jul 20
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (19 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is CA $154
CA $577 total
includes taxes & fees
Aug 16 - Aug 17
Rustic Retreat Across from Lake; Family Friendly!

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.8 out of 10, Exceptional, (6 reviews)
"Host was fast in responding to all questions and concerns. Location was good for being close to all shopping and eating. "
United States
Kim W.
The price is CA $246
CA $436 total
includes taxes & fees
Jul 19 - Jul 20
Bright 2-Bedroom Apartment Near Downtown Thomaston

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

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (37 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
The price is CA $272
CA $599 total
includes taxes & fees
Jul 19 - Jul 20
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is CA $125
CA $295 total
includes taxes & fees
Jul 20 - Jul 21
Happy Cottage Near Everything 11

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (3 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $176
CA $372 total
includes taxes & fees
Jul 22 - Jul 23
Cheerful Cottage with Loft 9

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
The price is CA $225
CA $432 total
includes taxes & fees
Jul 20 - Jul 21
Spacious 1 Bedroom Cottage Close to Everything 3

Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Pemaquid Beach
9.2 out of 10, Wonderful, (5 reviews)
"Loved our stay"
United States
Jeanne
The price is CA $309
CA $525 total
includes taxes & fees
Jul 21 - Jul 22
Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (429 reviews)
"Everything was great and the location was amazing. Right in the arts district and surrounded by interesting shops, amazing eats and coffee & right on the harbor."
United States
Gerald
The price is CA $249
CA $272 total
includes taxes & fees
Jul 20 - Jul 21
Trade Winds on the Bay

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (44 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is CA $315
CA $568 total
includes taxes & fees
Jul 25 - Jul 26
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (2 reviews)
"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...
United States
Christopher H.
The price is CA $277
CA $474 total
includes taxes & fees
Jul 18 - Jul 19
Romantic Coastal Escape near Harbor
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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Top Pleasant Point Hotel Reviews

Find out more about Pleasant Point

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pleasant Point. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Pleasant Point?

Yes, we offer vacation rentals close to popular local attractions in Pleasant Point, or you can choose a more remote option if you're looking for relaxation.

What's the top vacation rental in Pleasant Point?

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: Visitors like this Pleasant Point vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Pleasant Point?

Choose from 10 Expedia vacation rentals in Pleasant Point for a memorable vacation.

What’s there to see and do in Pleasant Point?

Explore the area and family-friendly sights such as Maine State Prison Store, or get out into nature at a spot like St. George River. In the larger area, you’ll find Marshall Point Lighthouse and Owls Head Transportation Museum.

What’s a vacation rental in Pleasant Point like?

Vacation rentals are private properties where you can stay for a couple of days or more in Pleasant Point. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.