Search Cottages in Pleasant Point

    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

In two weeks
5 Sep - 7 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Cottages in Pleasant Point

Peaceful.... Lakefront Cottage... Kayakers Paradise....
Exterior

Peaceful.... Lakefront Cottage... Kayakers Paradise....

10.0 out of 10, Exceptional, (56)
"Beautiful, peaceful location. Great fishing. Comfortable, immaculate cabin."
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Boothbay Harbor Cottage Overlooking Mill Cove
Marina

Boothbay Harbor Cottage Overlooking Mill Cove

9.8 out of 10, Exceptional, (22)
"Clean, close to downtown."
Boothbay Harbor Cottage Overlooking Mill Cove
Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
Beach

Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free

10.0 out of 10, Exceptional, (48)
"Loved it on every level. Cottage was super clean and loved the style and the size. There is a pond and a field out back with fireplaces and areas to sit and hang out. Perfect for the morning walk with the dog. The cottages are fairly close to each other but each had their own very private deck so I didn’t mind at all. Communication from the hosts was also perfect whilst leaving you enough privacy. Would come back for sure. "
Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Property grounds

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

10.0 out of 10, Exceptional, (46)
"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
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, (81)
"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 modern guest cottage across from Spruce Point Inn Pet Friendly!
Terrace/patio

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!
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
TV

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.4 out of 10, Exceptional, (51)
"This home is so wonderful to stay in. My sister and I find this to be the perfect place to meet each other and relax with our family. Beautiful space. "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Happy Cottage Near Everything 11
Outdoor dining

Happy Cottage Near Everything 11

8.0 out of 10, Very Good, (1)
"Very comfortable, clean small cottage. We slept great in the bed that was provided and it had a futon in the living area . We recommend that only 2 people stay there. They had a toaster oven , a full refrigerator and a coffee maker. It is very close to Route 1, Boothbay Harbor and Damariscotta. "
Happy Cottage Near Everything 11
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
TV, fireplace, DVD player, books

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.2 out of 10, Wonderful, (68)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Lakefront Cozy Cottage
Terrace/patio

Lakefront Cozy Cottage

9.8 out of 10, Exceptional, (69)
"A perfect retreat for two people with lovely outdoor seating area. "
Lakefront Cozy Cottage
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Terrace/patio

‘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 2-bedroom cottage conveniently located with all the amenities!
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"It is conveniently located. Very clean. Nice big yard."
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (144)
"This is always our very favorite place!!!"
Updated lake cottage right on Damariscotta Lake.
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, (84)
"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
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (19)
"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
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Terrace/patio

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

9.6 out of 10, Exceptional, (24)
"Very nice all the basics covered. Close to the harbor, very quiet."
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Dog-friendly cottage with amazing bay views & deck - snowbirds welcome
Exterior

Dog-friendly cottage with amazing bay views & deck - snowbirds welcome

9.0 out of 10, Wonderful, (30)
"Very comfortable, clean, and in a great location near town."
Dog-friendly cottage with amazing bay views & deck - snowbirds welcome
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Exterior

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

10.0 out of 10, Exceptional, (106)
"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
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"We had the best week at Sea Breeze in our first trip to Maine! After a long drive, we were stunned to turn the corner to find our home overlooking a gorgeous seaside, situated on a quiet, walkable, friendly street. When we stepped inside, we found the house to be a clean, cozy, and quiet haven that had plenty of space to relax, play board games, and enjoy family breakfasts around the table. There was ample space in the fridge and freezer for all of our locally-purchased groceries, the kitchen...
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Terrace/patio

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (69)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
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

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

10/10 Excellent
"Nice Place"
Gary 1-night trip
Posted 16 hours ago
Bluebird Ocean Point Inn

Frequently asked questions

Why book your cottage in Pleasant Point with Expedia?
Expedia has some superb cottages in Pleasant Point, so start packing for an unforgettable vacay on nature's doorstep. If you're on a budget, click on how much you want to spend and the star rating of your property. Or, make the most of our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Pleasant Point?
With Expedia's convenient filter tool, locating cheap cottages in Pleasant Point is a cinch. To view properties that are very pocket friendly, narrow your search results by budget, amenities and star rating.