Pleasant Point Vacation 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

Tonight
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

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, (256)
"Location is amazing."
The price is CA $242
CA $264 total
includes taxes & fees
Sep 3 - Sep 4
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
8.8 out of 10, Excellent, (11)
"Very peaceful !"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
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
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (145)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.
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...
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 CA $382
CA $806 total
includes taxes & fees
Sep 27 - Sep 28
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
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 CA $177
CA $273 total
includes taxes & fees
Sep 8 - Sep 9
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)
"We had a great stay while in town for a family event. We were ecstatic to be able to take our family dog with us on the trip. The view from the back deck was incredible and close to many local parks for hiking."
The price is CA $266
CA $520 total
includes taxes & fees
Sep 2 - Sep 3
Comfortable, Close to Town Home, with Oceanview.
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)
"Another great stay"
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
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, (131)
"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
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, (87)
"We enjoyed our stay in every way. The house is very clean and comfortable….the gorgeous views were a lucky strike extra. This is a special place!"
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
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!
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Terrace/patio

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

6.0 out of 10, (2)
"Nice place to stay for a quick trip to the area! Would stay there again. "
The price is CA $171
CA $264 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
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.
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
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, (123)
"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
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, (122)
"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
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
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

Find out more about Pleasant Point

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Point vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Point vacation rentals we have selected for you start as low as CA $177 per night. Entering your travel dates in the search wizard 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

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?

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 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.