Pleasant Point Vacation Rentals

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Vacation Rentals in Pleasant Point

Tranquil Coastal Sanctuary with Chef's Kitchen, Jacuzzi Tub and Water Views

Tranquil Coastal Sanctuary with Chef's Kitchen, Jacuzzi Tub and Water Views

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (233)
"Great place to stay...everything was great"
The price is CA $299
CA $326 total
includes taxes & fees
Jul 22 - Jul 23
Trade Winds on the Bay

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
9.4 out of 10, Exceptional, (8)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Dog-friendly bay view home - water views, dock access

6.4 out of 10, (6)
"Nice and quiet. Beautiful view of the water"
Dog-friendly bay view home - water views, dock access

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.8 out of 10, Exceptional, (25)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (37)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

10.0 out of 10, Exceptional, (89)
"Property was great for family gathering"
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

10.0 out of 10, Exceptional, (1)
"We rented this house for a short stay in Boothbay Harbor. Great house. We had a party of five and did not even use all of the bedrooms. We had a 92 year old with mobility issues (using walker) with us and the house was ideal for him with two bedrooms and a bathroom on the ground floor. Great side porch with barbecue that we used several nights. Great location, quiet, but able to walk into town. Five minute drive to Coastal Maine Botanical Gardens. Great communication with rental agency. We would...
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

Simple living in Midcoast Maine

10.0 out of 10, Exceptional, (1)
"Great location, close to everything I wanted to do. Grocery store and restaurants near by.. state parks and preserves to walk. Condo was clean and comfortable,with easy access. Nice balcony looking out over the green space in the back. Great place to have coffee in the morning - I even saw a deer one morning!"
Simple living in Midcoast Maine

Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

10.0 out of 10, Exceptional, (125)
"This was by far one of the best places we have ever stayed , it was so well decorated and stocked with anything you would need. Spotlessly clean and really felt like home. If I ever get back to Maine it will be my go to place to stay"
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

9.0 out of 10, Wonderful, (18)
"Great place for a romantic get a way. Great lobster just down the road."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (98)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

10.0 out of 10, Exceptional, (116)
"Superbly clean, great location!"
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Well-located, dog-friendly home - walk to footbridge & Barrett Park

9.4 out of 10, Exceptional, (33)
"A nice, quiet location that is just a walk away from a pretty town, and not too far of a drive away from many great places to visit along the coastline."
Well-located, dog-friendly home - walk to footbridge & Barrett Park

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (74)
"Fantastic location, owners were nearby and easy to communicate with for any questions. Perfect views and cozy apartment for our family of 3. Would definitely stay here again!"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (88)
"My daughter and I enjoyed our stay."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Morning sun, coffee in hand, a good book and so much more...

9.8 out of 10, Exceptional, (80)
"Really enjoyed being on the lake and so close to town."
Morning sun, coffee in hand, a good book and so much more...

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

10.0 out of 10, Exceptional, (115)
"We had a lovely time staying at your wonderfully cozy and charming property - thank you for a great experience!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.2 out of 10, Wonderful, (15)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

Lakefront Cozy Cottage

9.8 out of 10, Exceptional, (66)
"We loved our stay at the little cottage by the pond. It was peaceful and relaxing."
Lakefront Cozy Cottage
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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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?

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun: You might want to consider this vacation home rental near Pleasant Point, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 Maine Coastal Islands National Wildlife Refuge. 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.