Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Pleasant Point

Water view
Trade Winds on the Bay

Trade Winds on the Bay

3.5 star property
Rockland
8.4 out of 10, Very Good, (311)
"Basic room , clean and perfect for our stay. "
United States
Deborah
$87 nightly
The price is $95
Nov 11 - Nov 12
Total with taxes and fees
Trade Winds on the Bay
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
$437 nightly
The price is $477
Nov 11 - Nov 12
Total with taxes and fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Terrace/patio
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, (7)
"Nice place to stay for a quick trip to the area! Would stay there again. "
United States
Lisa M.
$200 nightly
The price is $218
Dec 1 - Dec 2
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Fridge, microwave, oven, stovetop
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D

Tenants Harbor
9.8 out of 10, Exceptional, (74)
"The view at sunrise is phenomenal. Place is extremely clean, neat and comfortable. We really enjoyed our stay."
United States
Scott P.
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
Fridge, microwave, oven, stovetop
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

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

Boothbay Harbor
9.2 out of 10, Wonderful, (100)
"This home is situated on a quiet street, but within a half-mile walking distance to the shops, restaurants, and puffin cruise piers. The house is comfortable and well-equipped, with several nice extras. The house was very clean when we arrived. The location is perfect, and we enjoyed sitting outside by the cove."
United States
Debbie A.
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Interior
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
9.6 out of 10, Exceptional, (83)
"Our family enjoyed staying in this cute cottage. The host was very helpful and quick to respond when we had trouble getting into the location upon arrival. We had a great time hanging out on the front porch and relaxing in the evening. We definitely wished we could have stayed another night or two to relax and explore the area a little more, maybe sometime in the future."
United States
Laura C.
$306 nightly
The price is $333
Nov 11 - Nov 12
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Property grounds
Morning sun, coffee in hand, a good book and so much more...

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

Camden
9.8 out of 10, Exceptional, (90)
"Lovely property, cozy and nice location. Nice property owner."
United States
DeAnn J.
Morning sun, coffee in hand, a good book and so much more...
Fridge, microwave, oven, stovetop
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

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

Boothbay Harbor
9.4 out of 10, Exceptional, (3)
"We appreciated being so close to the town area. It was even a walkable distance if you don’t mind the hills on the way home. Found the home to be very clean and the kitchen was well equipped. Nice and private yard."
United States
Lisa L.
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort
Smart TV, DVD player, books
Family Home in Rockport, ME, 5 minutes away from Camden, ME.

Family Home in Rockport, ME, 5 minutes away from Camden, ME.

Rockport
9.6 out of 10, Exceptional, (41)
"Property owners offered effective check in and communication."
United States
Adele B.
Family Home in Rockport, ME, 5 minutes away from Camden, ME.
Property grounds
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

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

South Thomaston
9.2 out of 10, Wonderful, (20)
"Great place for a romantic get a way. Great lobster just down the road."
United States
G Allen H.
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Fridge, microwave, oven, stovetop
Dog-friendly bay view home - water views, dock access

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

Boothbay Harbor
6.8 out of 10, (9)
"We had a great time and Sea View was perfect for oir stay!"
United States
Norman M.
Dog-friendly bay view home - water views, dock access
Outdoor dining
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor
10.0 out of 10, Exceptional, (20)
"Great location"
United States
Lynn D.
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Beach towels
Owls Head Village Post Office

Owls Head Village Post Office

Owls Head
10.0 out of 10, Exceptional, (166)
"We have stayed here several times and coming back just brings us joy. Mornings on the balcony with coffee and a book are the best. Access to kayaks and food right next door just can’t be beat. "
United States
Sarah W.
Owls Head Village Post Office
Fridge, microwave, oven, stovetop
Newly renovated 2-bedroom cottage conveniently located with all the amenities!

Newly renovated 2-bedroom cottage conveniently located with all the amenities!

2.0 star property
Camden
9.8 out of 10, Exceptional, (12)
"This property was perfect! Exactly as described in the posting. Very clean and had all amenities you could need. Location was also wonderful. Close to downtown but still very quiet. We all enjoyed it."
United States
Susie C.
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
Property grounds
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock

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

Port Clyde
10.0 out of 10, Exceptional, (82)
"A piece of heaven on earth! Very peaceful. Very responsive well managed property. We’ll be back. "
United States
Mary A.
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
Smart TV
Shipwright @ The Offshore House

Shipwright @ The Offshore House

Boothbay
9.4 out of 10, Exceptional, (13)
"Room was as advertised. Clean, good location, easy check in/out. The Shipwright room had a cute little kitchenette and sitting area. "
United States
Virginia G.
$284 nightly
The price is $301
Nov 11 - Nov 12
Total with taxes and fees
Shipwright @ The Offshore House
Fridge, microwave, oven, stovetop
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

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

Boothbay Harbor
9.6 out of 10, Exceptional, (37)
"The view from the deck is wonderful. Property was clean; check-in a breeze."
United States
Michael V.
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Property grounds
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

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

Boothbay Harbor
10.0 out of 10, Exceptional, (104)
"Our third stay was just as charming as the first two. The beauty of the lake, the serene accommodations and locale cannot be topped. The apartment is so cozy and comfortable. We've stayed in many vacation rentals, but this is our favorite. We'll be back."
United States
Susan B.
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Terrace/patio
Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Boothbay Harbor
10.0 out of 10, Exceptional, (2)
"Cozy studio with an excellent location. Furnishings were nice, shower was fantastic and the front deck overlooking the water and town was perfect. "
United States
Jim S.
Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier
Outdoor dining
Oceanfront home on Lobster Cove with deck & shared firepit - walk to town

Oceanfront home on Lobster Cove with deck & shared firepit - walk to town

Boothbay Harbor
10.0 out of 10, Exceptional, (31)
"Great location and property. The home had a nice view of the water, steps away from the park, and the inside was cozy and clean. Comfortable beds and plenty of towels provided. Easy access to the town. Short drive to downtown parking or hop on the trolley at the park. Would definitely stay here again. We loved Boothbay Harbor and the Windjammer Days."
United States
Carol T.
Oceanfront home on Lobster Cove with deck & shared firepit - walk to town
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

Hampton Inn & Suites Rockland

Hampton Inn & Suites Rockland

10/10 Excellent
"Quiet, convenient "
ken 2-night trip
Posted 2 days ago
Hampton Inn & Suites Rockland

Find out more about Pleasant Point

Everything you need to know about Pleasant Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Point vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Point vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Point. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasant Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasant Point rentals

At Expedia, we put the best Pleasant Point vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasant Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Point vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views: You might want to consider this vacation home rental near Pleasant Point, which is located on the beach and has a patio, a garden, and air-conditioning to put you at ease 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 St. George River. In the larger area, you’ll find Marshall Point Lighthouse and Maine Coastal Islands National Wildlife Refuge.

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.