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Our top choices for Pleasant Point holiday rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (544 reviews)
"A lovely view and location"
United States
Garrett
The price is £85
includes taxes & fees
16 Nov - 17 Nov
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, (41 reviews)
"The perfect spot for quiet and privacy yet a short trip to town."
United States
jennifer
The price is £104
includes taxes & fees
21 Nov - 22 Nov
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, (59 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is £181
includes taxes & fees
16 Nov - 17 Nov
2 Bedroom Close to Town Home

4. Cheerful Cottage Close to Everything 13

Cheerful Cottage Close to Everything 13
Edgecomb
9.2 out of 10, Wonderful, (18 reviews)
"Clean, close to everything, great communication from the host, cozy!"
United States
Crystal B.
Cheerful Cottage Close to Everything 13

5. 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 £189
includes taxes & fees
1 Dec - 2 Dec
Peaceful, Centrally Located Home with Seasonal River Views

6. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (17 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 £178
includes taxes & fees
17 Nov - 18 Nov
Bright 2-Bedroom Apartment Near Downtown Thomaston

7. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"The cabin was clean and cozy! We enjoyed our stay."
United States
Caitlin R.
Cheerful Cottage with Loft 9

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (85 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is £300
includes taxes & fees
22 Nov - 23 Nov
Harbor/🦞 Pound Access & Views from Large Deck

9. 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 £125
includes taxes & fees
16 Nov - 17 Nov
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

10. 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, (46 reviews)
"I always enjoy staying at this place!"
United States
Stephen H.
The price is £281
includes taxes & fees
13 Dec - 14 Dec
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

11. Jenoalli Cozy one bedroom ap

Jenoalli Cozy one bedroom ap
Rockland
The price is £206
includes taxes & fees
22 Nov - 23 Nov
Jenoalli Cozy one bedroom ap

12. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.2 out of 10, Wonderful, (13 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is £125
includes taxes & fees
16 Nov - 17 Nov
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, (104 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 £241
includes taxes & fees
16 Nov - 17 Nov
Comfortable, Close to Town Home, with Oceanview.

14. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (8 reviews)
"The home is clean and very well stocked with anything you might need. Ty reached out to me to make sure everything was good and offered to bring anything I might need while staying there. Property is very well kept. I love the neighbors too. Bed was comfortable. We will be back next year."
United States
Sheila D.
The price is £177
includes taxes & fees
6 Dec - 7 Dec
Romantic Coastal Escape near Harbor

15. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (72 reviews)
"Lovely little cottage within a riverside resort. Perfect for a get-a-way for two! You can enjoy the river at the gazebo and landing; and the restaurant and bar are a perfect place to end your day of sightseeing."
United States
Mary Alise H.
The price is £219
includes taxes & fees
16 Nov - 17 Nov
A Spacious Vacation Cottage in Sheepscot Harbour

16. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is £403
includes taxes & fees
16 Nov - 17 Nov
Fully Updated Airy Historic Home in West Rockport

17. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (129 reviews)
"This place was the definition of relaxation! The access to West Harbor "Pond" (it's huge -- more like a lake!) was unbeatable! We were able to use the provided kayaks to explore the little islands in the water and to come really close to a pair of loons!"
United States
Melinda M.
The price is £243
includes taxes & fees
16 Nov - 17 Nov
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

18. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Edgecomb
9.8 out of 10, Exceptional, (90 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is £254
includes taxes & fees
14 Dec - 15 Dec
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

19. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
10.0 out of 10, Exceptional, (52 reviews)
"Enjoyed the property. The AC and laundry was great. Convenient for my purposes of visiting family. Calling was very helpful and responsive!"
United States
Jean D.
The price is £279
includes taxes & fees
16 Nov - 17 Nov
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

20. Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920

Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is £494
includes taxes & fees
16 Nov - 17 Nov
Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
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

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 £85 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.