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Pleasant Point Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pleasant Point holiday 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, (509 reviews)
"the views were incredible, staff friendly and accommodations comfortable."
United States
Allene
The price is AU$128
includes taxes & fees
28 Oct - 29 Oct
Trade Winds on the Bay
A wooden deck with outdoor furniture, a table, and a view of the water.

2. Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting

Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting
Port Clyde
9.8 out of 10, Exceptional, (59 reviews)
"Perfect!"
United States
Susan B.
The price is AU$331
includes taxes & fees
30 Oct - 31 Oct
Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (35 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is AU$221
includes taxes & fees
8 Oct - 9 Oct
Simplicity-Just what you need! STR24-20
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

4. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (55 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is AU$380
includes taxes & fees
1 Nov - 2 Nov
2 Bedroom Close to Town Home
A wooden deck with Adirondack chairs and a grill.

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (14 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 AU$357
includes taxes & fees
2 Nov - 3 Nov
Bright 2-Bedroom Apartment Near Downtown Thomaston
Outdoor dining

6. 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 AU$261
includes taxes & fees
11 Oct - 12 Oct
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A wooden deck with a glass door leading to a room.

7. 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 AU$321
includes taxes & fees
7 Oct - 8 Oct
Tiny Cottage Near Everything 10
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.
The price is AU$425
includes taxes & fees
2 Nov - 3 Nov
Peaceful, Centrally Located Home with Seasonal River Views
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

9. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (18 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
The price is AU$325
includes taxes & fees
27 Oct - 28 Oct
Cheerful Cottage Close to Everything 12
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, (11 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is AU$261
includes taxes & fees
12 Oct - 13 Oct
Peaceful Intown Studio ~ Walk to Shops & Dining
A grassy yard with a small table and chairs, a house, and a lake in the background.

11. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (23 reviews)
"Great location for visiting the coast."
United States
Sallie S.
Rustic Retreat Across from Lake; Family Friendly!
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

12. 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 AU$342
includes taxes & fees
2 Nov - 3 Nov
Cheerful Cottage with Loft 9
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

13. 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)
"Wonderful place at a great price!"
United States
Stephen H.
The price is AU$550
includes taxes & fees
20 Oct - 21 Oct
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A room with a large window offering a view of a snowy landscape and a body of water.

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (101 reviews)
"Great location close to town"
United States
Rich W.
The price is AU$518
includes taxes & fees
25 Oct - 26 Oct
Comfortable, Close to Town Home, with Oceanview.
A fenced garden area with a wooden gate, surrounded by greenery and trees.

15. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is AU$296
includes taxes & fees
10 Oct - 11 Oct
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
A small cabin with a wooden deck, surrounded by trees in a wooded area.

16. 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 AU$397
includes taxes & fees
3 Nov - 4 Nov
Spacious 1 Bedroom Cottage Close to Everything 3
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (82 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is AU$613
includes taxes & fees
2 Nov - 3 Nov
Harbor/🦞 Pound Access & Views from Large Deck
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

18. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (15 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is AU$285
includes taxes & fees
14 Oct - 15 Oct
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

19. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (83 reviews)
"We really enjoyed staying at this house! It was in a good location and was cute and cozy!"
United States
Victoria S.
The price is AU$854
includes taxes & fees
13 Oct - 14 Oct
Oceanview Bungalow Style Home in Owls Head
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

20. 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.
The price is AU$440
includes taxes & fees
25 Oct - 26 Oct
A Spacious Vacation Cottage in Sheepscot Harbour
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

Rockland Harbor Hotel

Rockland Harbor Hotel

8/10 Good
"Nice middle size hotel. Convenient to dining."
Leonard 1-night trip
Posted 5 hours ago
Rockland Harbor Hotel

Find out more about Pleasant Point

Everything you need to know about Pleasant Point holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pleasant Point holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Point holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Point holiday rentals we have selected for you start as low as AU$128 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pleasant Point rentals

At Expedia, we put the best Pleasant Point holiday 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 holiday.

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 holiday rentals in Pleasant Point?

Yes, there are holiday rentals close to the most popular sights in Pleasant Point, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pleasant Point has to offer?

Oceanview Bungalow Style Home in Owls Head: This holiday home rental outside of Pleasant Point 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Pleasant Point?

Choose from 8 Expedia holiday rentals in Pleasant Point for a memorable holiday.

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 wider area, you’ll find Marshall Point Lighthouse and Owls Head Transportation Museum.

What’s a holiday rental in Pleasant Point like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pleasant Point. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.