Pleasant Point Holiday Rentals from €102: Search Short-Term Rentals

Q: 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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pleasant Point holiday rentals

1. Trade Winds on the Bay

Rockland

Garrett

includes taxes & fees

15 Nov - 16 Nov

A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Rockland

jennifer

includes taxes & fees

14 Nov - 15 Nov

A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

3. 2 Bedroom Close to Town Home

Thomaston

Nita S.

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

4. Peaceful, Centrally Located Home with Seasonal River Views

Thomaston

Pastor Heidi G.

includes taxes & fees

1 Dec - 2 Dec

A wooden deck with Adirondack chairs and a grill.

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston

Alexis H.

includes taxes & fees

1 Dec - 2 Dec

A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

6. Spacious 1 Bedroom Cottage Close to Everything 5

Edgecomb

Theresa

A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

7. Cheerful Cottage with Loft 9

Edgecomb

Caitlin R.

includes taxes & fees

15 Nov - 16 Nov

A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

8. Happy Cottage Near Everything 11

Edgecomb

George

An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

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

Owls Head

Jeanette Q.

includes taxes & fees

22 Nov - 23 Nov

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

Waldoboro

includes taxes & fees

17 Nov - 18 Nov

A coastal area with a beach, forested land, and a few buildings.

11. Across the road from Pemaquid Beach: a wooded king-bed cabin for couples

Pemaquid Beach

Mia

A room with a large window offering a view of a snowy landscape and a body of water.

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

Owls Head

Ted H.

includes taxes & fees

16 Nov - 17 Nov

A white door with a glass panel, a white porch with a railing, and a framed picture on the wall.

13. Jenoalli Cozy one bedroom ap

Rockland

includes taxes & fees

20 Nov - 21 Nov

A bedroom with a bed, a bedside table, and a window with curtains.

14. Peaceful Intown Studio ~ Walk to Shops & Dining

Newcastle

Brian

includes taxes & fees

14 Nov - 15 Nov

A small cabin with a wooden deck, surrounded by trees in a wooded area.

15. Spacious 1 Bedroom Cottage Close to Everything 3

Edgecomb

Bruce O.

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

16. Cheerful Cottage Close to Everything 12

Edgecomb

Tom C.

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a sofa, a small table, and a view of a backyard through large windows.

17. Spacious 1 Bedroom Cottage Close to Everything 2

Edgecomb

Terrence F.

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

18. A Spacious Vacation Cottage in Sheepscot Harbour

Edgecomb

Mary Alise H.

includes taxes & fees

15 Nov - 16 Nov

A cozy bedroom with a wooden ceiling, a large bed with a blue blanket, a desk with a chair, and a window with curtains.

19. Cheerful Cottage with Loft Close to Everything 6

Edgecomb

Yaoyubai

includes taxes & fees

15 Nov - 16 Nov

A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

20. Fully Updated Airy Historic Home in West Rockport

Rockport

includes taxes & fees

14 Nov - 15 Nov

View all properties

Find holiday rentals that suit your style

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, apart-hotels, 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 favorite 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 depends 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 €102 per night. Entering your travel dates in the search wizard you might find 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.

Holiday Rentals in Pleasant Point

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pleasant Point holiday rentals

1. Trade Winds on the Bay

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

3. 2 Bedroom Close to Town Home

4. Peaceful, Centrally Located Home with Seasonal River Views

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

6. Spacious 1 Bedroom Cottage Close to Everything 5

7. Cheerful Cottage with Loft 9

8. Happy Cottage Near Everything 11

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

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

11. Across the road from Pemaquid Beach: a wooded king-bed cabin for couples

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

13. Jenoalli Cozy one bedroom ap

14. Peaceful Intown Studio ~ Walk to Shops & Dining

15. Spacious 1 Bedroom Cottage Close to Everything 3

16. Cheerful Cottage Close to Everything 12

17. Spacious 1 Bedroom Cottage Close to Everything 2

18. A Spacious Vacation Cottage in Sheepscot Harbour

19. Cheerful Cottage with Loft Close to Everything 6

20. Fully Updated Airy Historic Home in West Rockport

Find holiday rentals that suit your style

Find out more about Pleasant Point

Pleasant Point holiday rentals: An excellent choice for every season

How to find incredible deals on Pleasant Point rentals

Frequently Asked Questions

Can I find holiday rentals in Pleasant Point?

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

How many holiday rentals will I find in Pleasant Point?

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

What’s a holiday rental in Pleasant Point like?