Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Pleasant Point

Trade Winds on the Bay
Water view

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very Good, (252)
"Location is amazing."
Trade Winds on the Bay
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Fridge, microwave, oven, stovetop

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

2.0 star property
9.2 out of 10, Wonderful, (10)
"Very peaceful !"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (144)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Property grounds

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

10.0 out of 10, Exceptional, (102)
"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
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Outdoor dining

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

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

9.8 out of 10, Exceptional, (82)
"Really enjoyed being on the lake and so close to town."
Morning sun, coffee in hand, a good book and so much more...
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Terrace/patio

Newly Renovated Cozy Cove Cabin at White Anchor Inn

8.0 out of 10, Very Good, (2)
"As advertised, comfy bed cozy cabin. Would stay again "
The price is ￥22,827
￥34,031 total
includes taxes & fees
Sep 4 - Sep 5
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Comfortable, Close to Town Home, with Oceanview.
Interior

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (76)
"Clean"
The price is ￥28,497
￥55,783 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable, Close to Town Home, with Oceanview.
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Property grounds

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

10.0 out of 10, Exceptional, (130)
"Property was perfect for a stay of two. Morning coffee was enjoyed with a beautiful view of the water and comfy patio chairs. Second story bedroom loft had a wall of windows to showcase the ocean view. It was noted that the property owners put thought into every amenity. "
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Renovated home with water views, dock access, - dogs okay
Fridge, microwave, oven, stovetop

Renovated home with water views, dock access, - dogs okay

6.6 out of 10, (8)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, - dogs okay
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

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

9.6 out of 10, Exceptional, (76)
"We loved our stay here. This is a fantastic location and has everything you need to enjoy your stay in Boothbay. Bring eye masks though, the futon sleeper is going to get a lot of light from the windows."
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Outdoor dining

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. "
The price is ￥40,984
￥86,409 total
includes taxes & fees
Sep 27 - Sep 28
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
On the beach, sun loungers

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

10.0 out of 10, Exceptional, (121)
"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
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
Property grounds

Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock

10.0 out of 10, Exceptional, (78)
"Very pleased with the house, the location, everything!"
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Interior

Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

9.8 out of 10, Exceptional, (66)
"Beautiful and very cozy stay close to everything you’d want to do, hike, explore, enjoy. Whirlpool jets in the tub was great after a long hike and we loved stargazing on the terrace. "
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Exterior detail

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (85)
"My husband and I just retired and enjoyed this place immensely! Especially the fireplace and the quiet space."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (92)
"We enjoyed the view from this home and the location very much. Easy walkability to town and having Dunston’s right down the street was a fun perk. The communal spaces are small but cozy. The weather was rainy while we were there so we spent a lot of time nestled up reading and enjoying the view. My only complaint was there was no coffee provided—pretty small gripe and easily remedied!"
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
On the beach, sun loungers

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

10.0 out of 10, Exceptional, (122)
"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.
Interior

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

10.0 out of 10, Exceptional, (94)
"Beautiful home and scenery, hosts were communicative. "
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Make Shimmering River Retreat your Maine Coastal getaway!
Fridge, microwave, oven, stovetop

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (37)
"It was a very nice place for a family vacation. There was plenty of room for all of us (10).Yard and inside games provided along with kayaks for the river and a pool."
Make Shimmering River Retreat your Maine Coastal getaway!
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

Find out more about Pleasant Point

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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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 home 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 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.