Pleasant Point Vacation Rentals

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Check prices for these dates

Tonight
Aug 6 - Aug 7
Tomorrow
Aug 7 - Aug 8
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Pleasant Point

Trade Winds on the Bay
Enjoy breathtaking views of the water from this balcony.

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very Good, (245)
"Location is amazing."
$221 nightly
The price is $241
Sep 2 - Sep 3
Total includes taxes and fees
Trade Winds on the Bay
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Enjoy cooking in this kitchen with a central island, sink, and black appliances.

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

2.0 star property
9.4 out of 10, Exceptional, (9)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Terrace/patio

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

$184 nightly
The price is $200
Aug 17 - Aug 18
Total includes taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Terrace/patio

Newly Renovated Cozy Cove Cabin at White Anchor Inn

$212 nightly
The price is $231
Aug 31 - Sep 1
Total includes taxes and fees
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Enjoy a serene riverside setting with a picnic table and two chairs on this deck surrounded by trees.

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

8.8 out of 10, Excellent, (38)
"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
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
Sailing vessel offers a cabin and seating area for passengers.

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

9.6 out of 10, Exceptional, (75)
"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
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Relax on the lakeside deck with four Adirondack chairs, surrounded by a tranquil forest and serene lake views.

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

10.0 out of 10, Exceptional, (100)
"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
Dog-friendly bay view home - water views, dock access
Enjoy cooking in this well-equipped kitchen with a granite countertop, sink, and stainless steel appliances.

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
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Stairs lead down to a serene beach surrounded by lush greenery and a dense hedge.

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

10.0 out of 10, Exceptional, (127)
"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.
Comfortable, Close to Town Home, with Oceanview.
Enjoy a serene view of the surrounding landscape from the large window in this cozy retreat.

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (74)
"Clean"
$372 nightly
The price is $405
Sep 1 - Sep 2
Total includes taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Enjoy a serene beach experience with a clear view of the ocean and natural surroundings.

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

10.0 out of 10, Exceptional, (118)
"This property was more than we could have asked for. The view was spectacular the hosts were great and we had more amenities than we could have asked for."
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Cozy cabin interior with a high ceiling and exposed beams, featuring a round table and comfortable seating area.

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

10.0 out of 10, Exceptional, (92)
"Beautiful home and scenery, hosts were communicative. "
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Enjoy cooking in this well-equipped kitchen with a refrigerator, sink, and stove.

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

9.6 out of 10, Exceptional, (29)
"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
Elegant riverside retreat with breathtaking views and modern comforts
Traditional home with a gabled roof and chimney, set amidst a well-manicured lawn and lush greenery.

Elegant riverside retreat with breathtaking views and modern comforts

Elegant riverside retreat with breathtaking views and modern comforts
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Enjoy a serene beach experience with a clear view of the sea and distant landmasses.

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

10.0 out of 10, Exceptional, (118)
"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
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and light wood cabinetry.

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

10.0 out of 10, Exceptional, (2)
"We loved how spacious and accommodating this home was, as well as it's great proximity to downtown Boothbay Harbor."
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Enjoy a meal on the deck overlooking the water with a table set for two, featuring a blue and white checkered tablecloth, plates, cutlery, and a glass.

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

9.4 out of 10, Exceptional, (25)
"Perfect base for exploring the mid-coast region. "
$683 nightly
The price is $744
Aug 30 - Aug 31
Total includes taxes and fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK
Escape to a serene lakeside retreat surrounded by lush greenery and dense trees.

Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

2.0 star property
9.0 out of 10, Wonderful, (102)
"The place was very clean. Right on the water. Spectacular views. Sunrise in the morning. A great experience. A lovely get away. Want to go back again"
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK
A Charming Waterfront Cottage with Touches of Elegance
Enjoy a room with a high ceiling, large windows, and a view of the water.

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"My husband and our 1 year old daughter had a wonderful stay. The home is close to everything and has everything you may need. Would love to stay again. "
A Charming Waterfront Cottage with Touches of Elegance
Beautiful Studio in downtown Boothbay Harbor
Relax in this inviting living room with a sofa, armchair, and coffee table.

Beautiful Studio in downtown Boothbay Harbor

9.0 out of 10, Wonderful, (8)
"Very cozy comfortable and convenient. Every thing we needed. "
Beautiful Studio in downtown Boothbay Harbor
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

Ledges by the Bay

Ledges by the Bay

10/10 Excellent
"Great hotel right on the bay. Nice, spacious room. Very clean! Nicely decorated lobby and dining area. "
MaryAnn 2-night trip
Posted 6 hours ago
Ledges by 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?

Dog-friendly bay view home - water views, dock access: 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 Maine State Prison Store, 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 St. George River.

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.