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Pleasant Point Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pleasant Point vacation rentals

Lobby sitting area

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (519 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
$91 nightly
The price is $99
Nov 17 - Nov 18
Total with taxes and fees
Trade Winds on the Bay
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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
$139 nightly
The price is $152
Oct 20 - Oct 21
Total with taxes and fees
Simplicity-Just what you need! STR24-20
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

3. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (57 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
$239 nightly
The price is $261
Oct 28 - Oct 29
Total with taxes and fees
2 Bedroom Close to Town Home
A wooden deck with a glass door leading to a room.

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
$206 nightly
The price is $208
Oct 20 - Oct 21
Total with taxes and fees
Tiny Cottage Near Everything 10
Outdoor dining

5. 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
$166 nightly
The price is $181
Oct 19 - Oct 20
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A wooden deck with Adirondack chairs and a grill.

6. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (15 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.
$228 nightly
The price is $249
Nov 17 - Nov 18
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
A coastal area with a beach, forested land, and a few buildings.

7. Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

8. 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.
$270 nightly
The price is $294
Nov 16 - Nov 17
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

9. 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
$214 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
A bedroom with a bed, a bedside table, and a window with curtains.

10. 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
$166 nightly
The price is $181
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

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, (44 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
$367 nightly
The price is $400
Oct 20 - Oct 21
Total with taxes and fees
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

12. 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.
$379 nightly
The price is $413
Nov 1 - Nov 2
Total with taxes and fees
Harbor/🦞 Pound Access & Views from Large Deck
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

13. 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.
$221 nightly
The price is $232
Oct 19 - Oct 20
Total with taxes and fees
Cheerful Cottage with Loft 9
A compact kitchen with a dining table, two chairs, a sofa, a lamp, and a refrigerator.

14. 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
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
A room with a large window offering a view of a snowy landscape and a body of water.

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (102 reviews)
"Great location close to town"
United States
Rich W.
$328 nightly
The price is $358
Nov 10 - Nov 11
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

16. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (71 reviews)
"Great place and great restaurants."
United States
Julie D.
$268 nightly
The price is $292
Oct 25 - Oct 26
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
Exterior

17. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (6 reviews)
"A wonderful place to stay close walking distance to downtown Rockport"
United States
Joshua H.
$225 nightly
The price is $245
Oct 21 - Oct 22
Total with taxes and fees
Romantic Coastal Escape near Harbor
A small cabin with a wooden deck, surrounded by trees in a wooded area.

18. 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.
$259 nightly
The price is $274
Oct 26 - Oct 27
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

19. 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
$188 nightly
The price is $190
Oct 26 - Oct 27
Total with taxes and fees
Happy Cottage Near Everything 11
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

20. 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.
$211 nightly
The price is $221
Oct 26 - Oct 27
Total with taxes and fees
Cheerful Cottage Close to Everything 12
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

Fishermans Wharf Inn

Fishermans Wharf Inn

10/10 Excellent
"The room was very clean with a great view. The staff were very helpful. It was on the water and was beautiful"
Colt 1-night trip
Posted less than an hour ago
Fishermans Wharf Inn

Find out more about Pleasant Point

Everything you need to know about Pleasant Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Point vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Point vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Point. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasant Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $99 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasant Point rentals

At Expedia, we put the best Pleasant Point vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasant Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Point vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.