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Pleasant Point Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Pleasant Point holiday rentals

Living area

1. Bee Hive Cottage, Romantic Maine Waterfront Cottag

Bee Hive Cottage, Romantic Maine Waterfront Cottag
2.0 star property
Cushing
Bee Hive Cottage, Romantic Maine Waterfront Cottag
Interior

2. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.0 out of 10, Very good, (4 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is HK$1,765
HK$2,591 total
includes taxes & fees
19 Aug - 20 Aug
Come Spring Farm Airstream , Lake & farm animals
1 bedroom, WiFi

3. ComfyDome Pond-Side Glamping

ComfyDome Pond-Side Glamping
Jefferson
10.0 out of 10, Exceptional, (6 reviews)
"A lovely stay - Seth was very kind and attentive, and our starry night sky was beyond compare. We will come again! "
United States
Fiona S.
The price is HK$1,271
HK$1,590 total
includes taxes & fees
21 Aug - 22 Aug
ComfyDome Pond-Side Glamping
Outdoor dining

4. 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 HK$1,299
HK$1,621 total
includes taxes & fees
1 Sept - 2 Sept
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Exterior

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

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (28 reviews)
"Very clean and allows for easy access around the area! "
United States
Sarah V.
The price is HK$863
HK$1,300 total
includes taxes & fees
6 Sept - 7 Sept
Simplicity-Just what you need! STR24-20
Terrace/patio

6. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is HK$2,573
HK$5,917 total
includes taxes & fees
6 Sept - 7 Sept
Luxury Yurt at Seaside Farm in Friendship
Lobby sitting area

7. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (448 reviews)
"Great stay, great location."
United States
Jerold
The price is HK$1,481
HK$1,615 total
includes taxes & fees
17 Aug - 18 Aug
Trade Winds on the Bay
Property grounds

8. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.8 out of 10, Exceptional, (7 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 HK$1,138
HK$2,155 total
includes taxes & fees
1 Sept - 2 Sept
Bright 2-Bedroom Apartment Near Downtown Thomaston
Front of property

9. 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 HK$1,420
HK$3,849 total
includes taxes & fees
14 Aug - 15 Aug
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Smart TV

10. 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.
The price is HK$1,373
HK$2,625 total
includes taxes & fees
9 Sept - 10 Sept
Peaceful, Centrally Located Home with Seasonal River Views
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 HK$784
HK$1,282 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Smart TV

12. 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 HK$1,334
HK$2,591 total
includes taxes & fees
1 Sept - 2 Sept
2 Bedroom Close to Town Home
Coffee/tea maker, fridge, microwave, stovetop

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

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"We had a lovely time in Maine and enjoyed the farm house for our downtime and sleeping. It was exactly what we were looking for and would 100% stay here again and recommend it to others. Thank you!"
United States
Carrie Plympton F.
The price is HK$1,075
HK$3,908 total
includes taxes & fees
14 Aug - 15 Aug
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Coffee/tea maker, fridge, microwave, stovetop

14. 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 HK$1,020
HK$2,131 total
includes taxes & fees
10 Aug - 11 Aug
Spacious 1 Bedroom Cottage Close to Everything 5
Outdoor dining

15. 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 HK$886
HK$1,888 total
includes taxes & fees
7 Sept - 8 Sept
Tiny Cottage Near Everything 10
Coffee/tea maker, fridge, microwave, oven

16. 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.
The price is HK$1,883
HK$3,814 total
includes taxes & fees
31 Aug - 1 Sept
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Property grounds

17. 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 HK$1,412
HK$4,446 total
includes taxes & fees
19 Aug - 20 Aug
Oceanview Bungalow Style Home in Owls Head
Interior

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (96 reviews)
"Great location close to town"
United States
Rich W.
The price is HK$1,961
HK$3,523 total
includes taxes & fees
18 Aug - 19 Aug
Comfortable, Close to Town Home, with Oceanview.
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

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

10/10 Excellent
"Super friendly and accommodating staff. We are a family of 4 with 2 kids (7 & 10). Such a great place. Would strongly recommend."
Eric 2-night trip
Posted 10 hours ago
The Country Inn at Camden Rockport

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:

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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 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?

Comfortable, Close to Town Home, with Oceanview.: This holiday home rental outside of Pleasant Point offers a patio, a private garden and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Pleasant Point?

Choose from 9 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 Tenants Harbor Marina.

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.