Search Pleasant Point Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Pleasant Point Cottages

A Charming Waterfront Cottage with Touches of Elegance
Relax on the deck with a serene view of the lake and surrounding trees, surrounded by comfortable wicker chairs and a small table.

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
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Guests can enjoy serene lakeside views from the balcony of this house, which features a staircase leading to the water's edge.

Waterfront Cottage in South Bristol w/ private dock and lobster boat views

10.0 out of 10, Exceptional, (105)
"We stayed at the property for two nights for a family getaway after the holidays. The house was in a great location, beautiful views, spotlessly clean, and very well equipped. We loved waking up to the light hitting the water and being able to explore the beautiful peninsula. Great hikes a short drive away. We would gladly stay again! "
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Olde Post Office Cottage at Pemaquid Point
Surrounded by a lush garden, this charming house offers a serene retreat.

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (140)
"This is our second time staying here, and as before, it was delightful. Obvious that the owner puts a lot of care and thought into the place."
Olde Post Office Cottage at Pemaquid Point
Cheerful Cottage Close to Everything 12
Enjoy a tranquil moment on this deck surrounded by lush foliage.

Cheerful Cottage Close to Everything 12

9.4 out of 10, Exceptional, (12)
"Well appointed and comfortable cabin. Loved the retro fridge and microwave and sitting on the deck with a morning coffee. We awoke to a woodsy view every morning. The location was perfect for us; convenient to Wiscasset, Damariscotta and Pemaquid Point. Our host was fabulous with his timely communication and down east hospitality. If we pass through this way again, we will be sure to stay here again."
Cheerful Cottage Close to Everything 12
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Property grounds

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
Lakefront Cozy Cottage
Relax in a serene outdoor space with a hammock swing overlooking a calm lake, surrounded by lush greenery and distant hills.

Lakefront Cozy Cottage

9.8 out of 10, Exceptional, (68)
"We loved our stay at the little cottage by the pond. It was peaceful and relaxing."
Lakefront Cozy Cottage
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Relax on the covered porch with Adirondack chairs and a barbecue grill.

‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore

9.6 out of 10, Exceptional, (44)
"Tenants Harbor 🎉"
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Escape to a secluded cabin surrounded by a dense forest and a babbling stream.

Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Wonderful stay! comfortable cozy and cute, tidy cottage. Hosts are responsive and welcoming. Cottage is very well thought out and location is great. Would love to stay again!"
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Spacious 1 Bedroom Close to Everything 4
Guests can enjoy meals and relaxation on the deck surrounded by lush greenery.

Spacious 1 Bedroom Close to Everything 4

10.0 out of 10, Exceptional, (17)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Situated in a forested area, this cabin features a front porch, door with glass panels, and two windows.

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

9.6 out of 10, Exceptional, (83)
"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
Newly updated cottage directly on Maple Juice Cove
Relax on the deck overlooking the serene water, surrounded by comfortable seating and a wooden railing.

Newly updated cottage directly on Maple Juice Cove

9.8 out of 10, Exceptional, (35)
"The property was clean and updated. Cabins are much smaller than I expected with no storage for our suitcases or clothing. I wish fresh towels were easier to obtain. Pool and hot tub was nice. It is right off of a noisy road, the trucks going by at night made it quite loud. The air conditioner had a musty odor. Friendly relaxed atmosphere overall. "
Newly updated cottage directly on Maple Juice Cove
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Situated on a rocky ledge, two Adirondack chairs offer a serene lakeside view.

Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area

10.0 out of 10, Exceptional, (44)
"Beautiful property & so clean & well appointed, great location! Had everything we wanted for a wonderful vacation week!"
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Relax on the deck with Adirondack chairs and a small table, taking in the views of the surrounding neighborhood.

Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

9.8 out of 10, Exceptional, (36)
"I highly recommend this place for ocean lovers and only a 10 minute walk to the harbor"
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Enjoy serene lake views from a deck, surrounded by autumn foliage and rustic charm.

Cozy Cottage with spectacular salt water view / 3 Kayaks available/

9.8 out of 10, Exceptional, (45)
"This rustic cottage is a slice of true Maine. Lobster boats outside the window. Friendly people and lobster rolls. We would come again and again. John and Melanee are wonderful, as is the entire family."
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Maine ocean front cottage with spectacular views
Guests can enjoy serene views of the water from this cabin's glass door.

Maine ocean front cottage with spectacular views

10.0 out of 10, Exceptional, (26)
"This is out 2nd year in a row we stayed at the cottage, it's always a pleasure with the hosts being friendly and courteous. We love the cottage and especially the location, very peaceful with the sound, smell and view of the water."
Maine ocean front cottage with spectacular views
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
Overlooking a tranquil pond, this cabin features large windows and a cozy outdoor seating area with chairs.

Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden

10.0 out of 10, Exceptional, (77)
"Such a great place to go to , and had perfect weather all week , love it there !"
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
The Moonlight Cottage: At The Water's Edge With Beaches And Atlantic Views
Enjoy outdoor dining on the deck with a scenic view of the water and shoreline.

The Moonlight Cottage: At The Water's Edge With Beaches And Atlantic Views

10.0 out of 10, Exceptional, (96)
"Great place on the water a lovely area Went to Camden several days you have to try McLoons lobster Shack"
The Moonlight Cottage: At The Water's Edge With Beaches And Atlantic Views
"The Cottage " is Perfect couples retreat!
Escape to a serene retreat surrounded by lush greenery and dense trees.

"The Cottage " is Perfect couples retreat!

9.6 out of 10, Exceptional, (28)
"Lovely, quiet retreat. Would definitely stay again."
"The Cottage " is Perfect couples retreat!
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Relax on the deck with a view of the lake, surrounded by lounge chairs and a small table.

Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village

9.4 out of 10, Exceptional, (9)
"Incredible views!"
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Exterior

Charming Cottage with Ocean Views, Wifi, and Washer and Dryer

Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasant Point Hotel Reviews

Fishermans Wharf Inn

Fishermans Wharf Inn

10/10 Excellent
"Very clean and comfortable. Great pillow selection. The views are epic and truly a perfect location in BBH. We will be back. "
Natalie 3-night trip
Posted 11 hours ago
Fishermans Wharf Inn