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Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Pleasant Point vacation rentals

Terrace/patio

1. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is AED 1,109
AED 2,678 total
includes taxes & fees
8 Sep - 9 Sep
Luxury Yurt at Seaside Farm in Friendship
1 bedroom, WiFi (free), bed sheets

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

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (30 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is AED 397
AED 601 total
includes taxes & fees
14 Sep - 15 Sep
Simplicity-Just what you need! STR24-20
Property grounds

3. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.0 out of 10, Wonderful, (9 reviews)
"Host was fast in responding to all questions and concerns. Location was good for being close to all shopping and eating. "
United States
Kim W.
The price is AED 533
AED 1,009 total
includes taxes & fees
14 Sep - 15 Sep
Bright 2-Bedroom Apartment Near Downtown Thomaston
Lobby sitting area

4. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (455 reviews)
"Great stay, great location."
United States
Jerold
The price is AED 693
AED 756 total
includes taxes & fees
17 Aug - 18 Aug
Trade Winds on the Bay
Smart TV

5. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (35 reviews)
"Great Stay!"
United States
Pastor Heidi G.
Peaceful, Centrally Located Home with Seasonal River Views
House (3 Bedrooms) | Front of property

6. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
The price is AED 665
AED 1,802 total
includes taxes & fees
9 Sep - 10 Sep
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Smart TV

7. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (51 reviews)
"We enjoyed staying at this site but we had difficulty with the address. I would recommend putting the number 67 on the outside of the mud room door, which would make it much easier to find the location A member of our party had difficulty sleeping on the pull out couch and recommended a thicker mattress. We also smelled cigarettes upon entry into the building but once the door was open for a short time the smell went away. I would definitely stay at this site again when I the area."
United States
April
The price is AED 628
AED 1,213 total
includes taxes & fees
13 Sep - 14 Sep
2 Bedroom Close to Town Home
Coffee/tea maker, fridge, microwave, stovetop

8. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
The price is AED 503
AED 1,842 total
includes taxes & fees
9 Sep - 10 Sep
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Property grounds

9. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (67 reviews)
"Perfect home away from home. Very well stocked kitchen, the beds were very comfy and everything was just overall cozy. Such a serene location. We will definitely stay again next time we come to visit our grandkids. "
United States
Tina B.
The price is AED 661
AED 2,082 total
includes taxes & fees
19 Aug - 20 Aug
Oceanview Bungalow Style Home in Owls Head
Coffee/tea maker, fridge, microwave, oven

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, (38 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Terrace/patio

11. 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, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is AED 493
AED 753 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Coffee/tea maker, fridge, microwave, stovetop

12. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is AED 489
AED 1,014 total
includes taxes & fees
14 Sep - 15 Sep
Spacious 1 Bedroom Cottage Close to Everything 5
Outdoor dining

13. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.0 out of 10, Very Good, (3 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
The price is AED 411
AED 876 total
includes taxes & fees
8 Sep - 9 Sep
Tiny Cottage Near Everything 10
Smart TV, DVD player, books, video library

14. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (67 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is AED 639
AED 1,253 total
includes taxes & fees
28 Aug - 29 Aug
A Spacious Vacation Cottage in Sheepscot Harbour
Interior

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (97 reviews)
"Great location close to town"
United States
Rich W.
The price is AED 918
AED 1,649 total
includes taxes & fees
18 Aug - 19 Aug
Comfortable, Close to Town Home, with Oceanview.
Cottage (2 Bedrooms) | Interior

16. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is AED 485
AED 1,434 total
includes taxes & fees
18 Aug - 19 Aug
Rustic Retreat Across From Lake; Family Friendly!
Dining

17. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (8 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is AED 650
AED 813 total
includes taxes & fees
24 Aug - 25 Aug
Peaceful Intown Studio ~ Walk to Shops & Dining
2 bedrooms, iron/ironing board, bed sheets

18. 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 AED 474
AED 989 total
includes taxes & fees
8 Sep - 9 Sep
Cheerful Cottage with Loft 9
Exterior

19. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
The price is AED 584
AED 1,126 total
includes taxes & fees
8 Sep - 9 Sep
Spacious 1 Bedroom Cottage Close to Everything 3
Marina

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful house with a beautiful location!"
United States
Angel H.
The price is AED 816
AED 1,894 total
includes taxes & fees
18 Aug - 19 Aug
Harbor/🦞 Pound Access & Views from Large Deck
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

Trade Winds on the Bay

Trade Winds on the Bay

10/10 Excellent
"easy check in clean fresh smelling lobby and giftshop was a nice touch"
Amber 2-night trip
Posted 7 hours ago
Trade Winds on the Bay

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?

Comfortable, Close to Town Home, with Oceanview.: You might want to consider this vacation rental near Pleasant Point, which offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable 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.

How many vacation rentals will I find in Pleasant Point?

Choose from 9 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 Penobscot Marine Museum, or get out into nature at a spot like St. George River. In the larger area, you’ll find Marshall Point Lighthouse and Maine Coastal Islands National Wildlife Refuge.

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.