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Compare 146 Cottages in Pleasant Point with updated reviews, rates, and availability.

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, (79)
"This cottage is perfect for a couple looking to get away for a few days. Sunrises are majestic and stargazing is second to to none. McCloon’s Lobster Shack is amazing and has beautiful views of the sunset."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Oceanfront and Pet Friendly Cottage
Oceanfront and Pet Friendly Cottage
9.6 out of 10, Exceptional, (7)
"The quiet relaxing cottage and area was what I need to escape the AZ heat for a week! Enjoyed taking my dog for walks on the beach and everyone was very friendly. The cottage was very clean and once I was able to get the WiFi connected it was a great place to get some work done while having the ocean view. Would have stayed longer if there was an option to do laundry as other Vrbo’s in the area have."
Oceanfront and Pet Friendly Cottage
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Property grounds
Peaceful.... Lakefront Cottage... Kayakers Paradise....
10.0 out of 10, Exceptional, (50)
"Great "
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Spacious 1 Bedroom Close to Everything 4
Living area
Spacious 1 Bedroom Close to Everything 4
10.0 out of 10, Exceptional, (14)
"Very nice"
The price is AED 364
AED 844 total
includes taxes & fees
8 Oct - 9 Oct
Spacious 1 Bedroom Close to Everything 4
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.6 out of 10, Exceptional, (27)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Breathtaking Oceanfront Private Cottage
Beach
Breathtaking Oceanfront Private Cottage
10.0 out of 10, Exceptional, (56)
"Cute cozy cottage right on Penobscot Bay. Very thoughtfully supplied with honestly more updated conveniences and small appliances than we expected to find, given the rural setting. The spiral staircase to the bedroom was easily manageable. We did not mind the only bathroom being on the first floor. The view of the bay is just stunning. If you want quiet: a hawk flew over and we could hear the sound of its wings. The local lobster shack was a walkable distance. We found eggs for sale on...
Breathtaking Oceanfront Private Cottage
Classic Maine Cottage with ocean views
Quintessential Maine cottage with ocean views.
Classic Maine Cottage with ocean views
9.8 out of 10, Exceptional, (35)
"The house is amazing. Everything you needed and more. Such a serene location. "
Classic Maine Cottage with ocean views
Spacious 1 Bedroom Cottage Close to Everything 2
Room
Spacious 1 Bedroom Cottage Close to Everything 2
9.8 out of 10, Exceptional, (12)
"We had a wonderful stay. All was as expected. Jeff the host was in touch and helpful. My only suggestion would be a bit of decluttering. The cottage is wonderfully decorated, but we found ourselves having to move furniture and decor in order to get around. In particular in the bedroom there is no room for a suitcase, as there is a big comfy chair just under the open closet. It didn't impact our stay, but it made the place feel a little full. The location is great."
Spacious 1 Bedroom Cottage Close to Everything 2
Redbird Cottage. Charming respite w/ large wrap-around porch and ocean views
Exterior
Redbird Cottage. Charming respite w/ large wrap-around porch and ocean views
9.8 out of 10, Exceptional, (20)
"We've stayed at numerous places in Boothbay Harbor, and Redbird Nest is right up there with the best of them. Cherie's home is a cozy retreat nestled on the shoreline hills with wonderful views of Linekin Bay. The kitchen is well stocked with all the basics and a few things you wouldn't expect. Cherie is a thoughtful and accommodating who provides everything you will need to relax at home or explore the area. Our stay was just a long weekend, but it wasn't long enough! We will definitely be...
Redbird Cottage. Charming respite w/ large wrap-around porch and ocean views
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
Private kitchen
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
2.0 star property
10.0 out of 10, Exceptional, (3)
"Four days on coastal Maine. Chose Camden area so we had easy access to Arcadia National Park ( two hours to the north) and easy day trip to Boothbay area( two hours to the south) and there is plenty to do in Camden or take a trip over to Portland. "
Newly renovated 2-bedroom cottage conveniently located with all the amenities!
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
9.6 out of 10, Exceptional, (14)
"For a small cottage it was spacious, had modern amenities. The listing says harbor view but you have to look thru power lines, power poles and a lobster processing plant. The side stone steps are overgrown with vegetation making it hard to maneuver. All in all a good experience."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
9.4 out of 10, Exceptional, (39)
"Very impressed with communications with Vacasa. Clean like an upscale hotel. Sitting right by the lake was beautiful all times of day. Firepit at night w/toasted marshmallows a delight. Only negative was bed in masterbedroom was too soft. Other beds were fine. Nice amenities. Dog friendly."
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
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, (5)
"Great little, remodeled and updated cottage perfect for a couple and your fur baby. We stayed for almost a week as our return to Florida was delayed by hurricane Helene. The host was very accommodating and allowed us to extend our stay for 2 days. The cottage is just behind the Spruce Point Inn and is walkable to downtown. The cottage is extremely cozy with reading nooks and a great gas fireplace that heats up the space well with great ambiance. Fantastic experience with the host, great...
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Cheerful Cottage Close to Everything 12
Room
Cheerful Cottage Close to Everything 12
9.2 out of 10, Wonderful, (7)
"this cottage is very good for one or two people.The cottage is set up well and the use of space is ok.Everything is in good working order and the kitchen is good for using for easy meals.There is a TV and the WiFi worked well.Linens were good as well as the bed Linens. The mattress is a little soft but it could have been way worse. There were four pillows which is nice.All in All it is very fairly price for the region and time of year that I stayed"
Cheerful Cottage Close to Everything 12
A Charming Waterfront Cottage with Touches of Elegance
Here is the 44 foot porch where guests relax at Beckoning Bay Cottage
A Charming Waterfront Cottage with Touches of Elegance
10.0 out of 10, Exceptional, (93)
"Very quant and quiet location. Very clean and well kept! The owner was easy to contact and even toured the property with us so we knew where everything was! 5 star!! "
A Charming Waterfront Cottage with Touches of Elegance
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Tenants Harbor Vacation Rental | Studio | 1BA | 500 Sq Ft | Steps to Enter
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
9.6 out of 10, Exceptional, (38)
"Cute little private cottage close to everything! Just a few miles you can hop on the ferry and head to Mohegan Island a must see! Head in the opposite direction and head to Camden another beautiful spot! The covered porch was perfect for morning coffee and evening conversation and cocktails Defiantly will return to Pauls Cottage! "
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
9.8 out of 10, Exceptional, (15)
"Convenient base for all of your adventures in Wiscasset, in Westport and Boothbay, and in the wider midcoast region. Quiet side street lined with stately, historic homes from the 1800's. Rental comes with all the conveniences, plus a deck with table and comfortable chairs overlooking the private gardens of the larger house and a dell with tall shade trees, perfect just for sitting and letting your road-weariness melt away."
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
Olde post office
Spring
Olde post office
9.6 out of 10, Exceptional, (132)
"A nice small cottage, that's perfect for 1-2 people. It's a great location for exploring the Pemaquid peninsula. The cottage was clean and the description and picture showed exactly what you were getting. It is located on the main road down to the lighthouse and was busy on the weekend but only during daylight hours, but I was expecting that. I enjoyed my stay there and would take it again if I wanted to stay in Pemaquid. "
Olde post office
Dog-friendly cottage with amazing bay views & deck - snowbirds welcome
Dog-friendly cottage with amazing bay views & deck - snowbirds welcome
9.0 out of 10, Wonderful, (23)
"This rental was clean and the perfect size. The view out back is breathtaking. This rental showcases all of the natural beauty that Maine is famous for. The air conditioning was cold and the water in the shower was hot. All linens were crisp and white. The driveway was a challenge to navigate, however it is manageable. We hope to stay here again."
Dog-friendly cottage with amazing bay views & deck - snowbirds welcome
Two separate dog-friendly homes with water views & Linekin Bay Resort access
Two separate dog-friendly homes with water views & Linekin Bay Resort access
8.0 out of 10, Very Good, (5)
"This was a beautiful place to stay and had more parking than we expected. The only hiccups we had was that the check in code we were given was one digit off from what it actually was so we had a little trouble getting into the house. Also there is an outlet that was uncovered in the bedroom and we had a child touch it. Luckily the child wasn’t harmed but this should definitely be addressed if there’s any little ones staying on the property. The houses were very clean and the only reason I gave...
Two separate dog-friendly homes with water views & Linekin Bay Resort access
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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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Other property types in Pleasant Point

Trade Winds on the Bay
Interior
Trade Winds on the Bay
3.0 star property
8.0 out of 10, Very Good, (110)
"The ROKU TV for TV entertainment is unacceptable. The front desk clerk actually had to sign into his private Spectrum account so we could watch network TV. Also, having to pay a premium cost for coffee and tea is unacceptable. We probably won’t stay there again for our yearly visit to Rockland. "
Trade Winds on the Bay
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Beach
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
9.8 out of 10, Exceptional, (36)
"Exactly as described, but better. Words can’t describe waking up each morning and seeing the great view and watching the activities of a small lobster harbor. Great location, comfortable bed. Everything we needed. "
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
9.8 out of 10, Exceptional, (56)
"Perfect for my husband and I. Great view on the water."
Dazzling ocean-view house with fireplace, deck, firepit, central AC, & W/D
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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