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Pleasant Point Vacation Rentals

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Our top choices for Pleasant Point vacation rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (536 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
The price is CA $135
CA $147 total
includes taxes & fees
Nov 3 - Nov 4
Trade Winds on the Bay

2. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (37 reviews)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
The price is CA $126
CA $189 total
includes taxes & fees
Nov 5 - Nov 6
Simplicity-Just what you need! STR24-20

3. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
8.8 out of 10, Excellent, (58 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is CA $161
CA $347 total
includes taxes & fees
Nov 3 - Nov 4
2 Bedroom Close to Town Home

4. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is CA $112
CA $255 total
includes taxes & fees
Nov 3 - Nov 4
Tiny Cottage Near Everything 10

5. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (19 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
The price is CA $109
CA $262 total
includes taxes & fees
Nov 3 - Nov 4
Cheerful Cottage Close to Everything 12

6. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (16 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is CA $169
CA $321 total
includes taxes & fees
Nov 4 - Nov 5
Bright 2-Bedroom Apartment Near Downtown Thomaston

7. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (41 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is CA $175
CA $364 total
includes taxes & fees
Dec 1 - Dec 2
Peaceful, Centrally Located Home with Seasonal River Views

8. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is CA $203
CA $241 total
includes taxes & fees
Nov 3 - Nov 4
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

9. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $117
CA $271 total
includes taxes & fees
Nov 3 - Nov 4
Cheerful Cottage with Loft 9

10. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (84 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is CA $198
CA $577 total
includes taxes & fees
Nov 3 - Nov 4
Harbor/🦞 Pound Access & Views from Large Deck

11. 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, (45 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
The price is CA $208
CA $494 total
includes taxes & fees
Nov 4 - Nov 5
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

12. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (12 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is CA $203
CA $241 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful Intown Studio ~ Walk to Shops & Dining

13. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (103 reviews)
"We weren’t even there for 24 hours. It was a great stop on the coast. Close to Rockland and a nice view of the ocean."
United States
Ted H.
The price is CA $245
CA $472 total
includes taxes & fees
Nov 3 - Nov 4
Comfortable, Close to Town Home, with Oceanview.

14. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is CA $164
CA $323 total
includes taxes & fees
Nov 3 - Nov 4
Spacious 1 Bedroom Cottage Close to Everything 3

15. Jenoalli Cozy one bedroom ap

Jenoalli Cozy one bedroom ap
Rockland
The price is CA $189
CA $378 total
includes taxes & fees
Nov 9 - Nov 10
Jenoalli Cozy one bedroom ap

16. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is CA $200
CA $774 total
includes taxes & fees
Nov 6 - Nov 7
Fully Updated Airy Historic Home in West Rockport

17. 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 $91
CA $242 total
includes taxes & fees
Nov 9 - Nov 10
Happy Cottage Near Everything 11

18. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (72 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is CA $200
CA $384 total
includes taxes & fees
Nov 3 - Nov 4
A Spacious Vacation Cottage in Sheepscot Harbour

19. Cheerful Cottage with Loft Close to Everything 6

Cheerful Cottage with Loft Close to Everything 6
Edgecomb
9.4 out of 10, Exceptional, (11 reviews)
"Very clean and comfortable little cottage. Host responds and communicates effectively. Very nice experience."
United States
Yaoyubai
The price is CA $117
CA $282 total
includes taxes & fees
Nov 9 - Nov 10
Cheerful Cottage with Loft Close to Everything 6

20. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is CA $112
CA $274 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 1 Bedroom Cottage Close to Everything 5
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?

Oceanview Bungalow Style Home in Owls Head: You might want to consider this vacation home rental near Pleasant Point, which is located by the ocean and has a balcony, a terrace, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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 8 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.