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Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (499 reviews)
"Its a place to stay."
United States
Todd
The price is ￥12,886
￥14,046 total
includes taxes & fees
Oct 20 - Oct 21
Trade Winds on the Bay
A wooden deck with two blue Adirondack chairs, surrounded by white flowers and trees.

2. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is ￥35,732
￥97,382 total
includes taxes & fees
Sep 30 - Oct 1
Luxury Yurt at Seaside Farm in Friendship
Outdoor dining

3. 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 ￥23,277
￥28,801 total
includes taxes & fees
Oct 2 - Oct 3
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A wooden deck with a glass door leading to a room.

4. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.8 out of 10, Excellent, (5 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is ￥14,470
￥32,840 total
includes taxes & fees
Sep 30 - Oct 1
Tiny Cottage Near Everything 10
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

5. 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 ￥15,300
￥23,884 total
includes taxes & fees
Oct 8 - Oct 9
Simplicity-Just what you need! STR24-20
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, (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 ￥20,621
￥38,777 total
includes taxes & fees
Oct 27 - Oct 28
Bright 2-Bedroom Apartment Near Downtown Thomaston
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

7. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (54 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 ￥19,676
￥41,178 total
includes taxes & fees
Oct 27 - Oct 28
2 Bedroom Close to Town Home
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, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is ￥23,435
￥45,431 total
includes taxes & fees
Oct 20 - Oct 21
Peaceful, Centrally Located Home with Seasonal River Views
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

9. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.4 out of 10, Very good, (10 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is ￥24,378
￥35,144 total
includes taxes & fees
Oct 5 - Oct 6
Newly Renovated Cozy Cove Cabin at White Anchor Inn
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 ￥22,806
￥28,287 total
includes taxes & fees
Sep 30 - Oct 1
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)
"Wonderful place at a great price!"
United States
Stephen H.
The price is ￥31,482
￥64,856 total
includes taxes & fees
Oct 26 - Oct 27
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

12. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (18 reviews)
"Great experience, great location! Would highly recommend."
United States
Lynn R.
The price is ￥14,639
￥34,342 total
includes taxes & fees
Oct 26 - Oct 27
Cheerful Cottage Close to Everything 12
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.
The price is ￥16,514
￥36,371 total
includes taxes & fees
Oct 5 - Oct 6
Cheerful Cottage with Loft 9
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

14. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (80 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 ￥35,388
￥92,232 total
includes taxes & fees
Oct 13 - Oct 14
Oceanview Bungalow Style Home in Owls Head
A grassy yard with a small table and chairs, a house, and a lake in the background.

15. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
The price is ￥18,889
￥59,419 total
includes taxes & fees
Sep 30 - Oct 1
Rustic Retreat Across From Lake; Family Friendly!
A room with a large window offering a view of a snowy landscape and a body of water.

16. 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 ￥31,482
￥57,478 total
includes taxes & fees
Oct 26 - Oct 27
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.

17. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (70 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is ￥22,507
￥45,105 total
includes taxes & fees
Sep 30 - Oct 1
A Spacious Vacation Cottage in Sheepscot Harbour
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

18. 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 ￥33,029
￥74,683 total
includes taxes & fees
Oct 13 - Oct 14
Harbor/🦞 Pound Access & Views from Large Deck
A living room with a flat-screen TV mounted on a wall with vertical wooden panels, a black entertainment unit below, a brown leather sofa, a glass coffee table with books and a sign, and a large green vase with white flowers.

19. Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58

Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58
Rockland
10.0 out of 10, Exceptional, (2 reviews)
"Perfect stay"
United States
Kayla G.
The price is ￥36,662
￥71,163 total
includes taxes & fees
Sep 30 - Oct 1
Jenoalli cozy 3 bedrooms and 2 bathrooms STR26-58
A fenced garden area with a wooden gate, surrounded by greenery and trees.

20. 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 ￥21,233
￥31,716 total
includes taxes & fees
Oct 1 - Oct 2
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
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

Harborline Hotel

Harborline Hotel

10/10 Excellent
"Loved staying here! Would recommend!"
Marley 2-night trip
Posted 7 hours ago
Harborline Hotel

Find out more about Pleasant Point

Search for holiday rentals in Pleasant Point on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasant Point using one of the methods below:

  • View our selection of featured holiday rentals in Pleasant Point
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Look no further and take a look at our great range of rental properties in Pleasant Point!

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.