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Compare 140 Cottages in Pleasant Point with updated reviews, rates, and availability.

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (98)
"We were having a delightful stay until we noticed that there was no heat but from the fire place. Unfortunately, we had to leave in the middle of our stay. Vrbo gave us a refund. I would stay there again. Lovely and sunny. Excellent Property Manager."
A Charming Waterfront Cottage with Touches of Elegance

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (135)
"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

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

9.4 out of 10, Exceptional, (31)
"Very cozy house in an absolutely lovely spot. We really enjoyed the outdoor space and the peace and quiet. "
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

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

9.0 out of 10, Wonderful, (17)
"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

9.4 out of 10, Exceptional, (43)
"Lovely home. Rooms modern and large, lots of toiletries provided. One small issue would be that the hot water takes a very long time to heat up. Loved the doggie poop station!!"
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

Breathtaking Oceanfront Private Cottage

10.0 out of 10, Exceptional, (60)
"Stayed for a longweekend in November. The cottage by the sea is literally right on the sea, the views are breathtaking, the sunrise gorgeous and we were lucky to have beautiful weather. The host thought of everything, the cottage has everything you need to make a wonderful stay. Would definitely return. Rockland is about a 15 min drive and a great place to visit."
Breathtaking Oceanfront Private Cottage

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

Quiet & Lovely Lakefront Cottage for Families!

9.6 out of 10, Exceptional, (13)
"Loved this spot. The lake was beautiful. We had a wonderful time even though the weather was bad a few days. The cabin was so cute and decorated very nice. The kitchen was stocked well. We had everything we needed. Loved hearing the loons at night. It wasn't too far from Camden that we visited frequently. I hope to come back there some day."
Quiet & Lovely Lakefront Cottage for Families!

Sheepscot Overlook Cottage

10.0 out of 10, Exceptional, (4)
"Very convenient location for mid-Maine. Didn't know the unit was three levels from description. Kitchen fairly well stocked. TV in every room. Good internet. Checkout procedure was a little strict, stripping sheets, putting away all dishes, garbage delivered to dumpster."
Sheepscot Overlook Cottage

Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

7.4 out of 10, Good, (3)
"We had a great stay at Depatsy’s camp with our 10mo old son and pup. The house was cozy, spacious and had everything we needed. The house was in a perfect location with access to the water and kayaks/paddle boards. We spent a lot of time on the patio enjoying the view and using the fire pit. Would definitely return for another trip! "
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

Cheerful Cottage Close to Everything 13

9.6 out of 10, Exceptional, (9)
"Cozy, clean, and conveniently located for accessing many peninsulas. Just off Rt 1- noise not a problem."
Cheerful Cottage Close to Everything 13

Updated Tiny House: Walk to Wiscasset Village

8.0 out of 10, Very Good, (5)
"Great location, easy to get to lots of coastal regions. Property is clean and cozy."
Updated Tiny House: Walk to Wiscasset Village

Spacious 1 Bedroom Cottage Close to Everything 5

10.0 out of 10, Exceptional, (6)
"Everything was great. We had a minor ‘blip’ when the morning of our arrival, the hot water went out in our cabin. Our host reached out and offered an alternative. No biggie and everything went well. We appreciated Jeff's willingness to find a solution. "
Spacious 1 Bedroom Cottage Close to Everything 5

Lakefront Home w/ Beautiful Water Views Dock and Canoes Available - Dogs OK

8.0 out of 10, Very Good, (10)
"I wish I could give 5 stars, but I can’t. We arrived on a Tuesday afternoon, at 4:30. We unlocked the door and entered into a powerful smell. Campfire. Black soot up the front of the fireplace and the smell was awful. And of coarse, we are super sensitive to the smell. Looking around, I found the couch to be filthy, every screen had nasty cobwebs, dirt on the floor, bedding filthy, mold on the shower floor, Bathroom faucet was disgusting and obviously not cleaned . I was profoundly disappointed,...
Lakefront Home w/ Beautiful Water Views Dock and Canoes Available - Dogs OK

Boothbay - Ocean Point home w/ screened porch, amazing view & water access

9.2 out of 10, Wonderful, (21)
"Peaceful with amazing views!"
Boothbay - Ocean Point home w/ screened porch, amazing view & water access

Cheerful Cottage with Loft 9

10.0 out of 10, Exceptional, (2)
"We had a lovely weekend stay at this cozy cabin. Super clean, all the amenities needed for our small family, 2 adults + 3 year old. Convenient location, we would book here again when we are back in the area. "
Cheerful Cottage with Loft 9

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

9.8 out of 10, Exceptional, (38)
"I had an excellent visit. The kitchen was well stocked with utensils and small appliances. Everything was super clean; magazines and books were available (as well as good WiFi). I never turned the tv on as the view was spectacular. I wasn’t able to have an outdoor fire due to weather but everything was great. I hope to return. I look forward to doing more exploring as the area is beautiful. Also, very responsive with owners live next door. Thanks for offering up this quant little cabin for...
Cozy Cottage with spectacular salt water view / 3 Kayaks available/

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

9.6 out of 10, Exceptional, (41)
"Everything was as expected or better. Great directions made it easy to find. Place was well stocked, super clean, very comfortable. Neighborhood is great. And when I needed something, the property manager jumped to help at record speed. Will definitely go back. :-)"
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore

Spacious & tranquil waterfront hideaway on Muscongus Sound

7.6 out of 10, Good, (25)
"Nice location, nice house. The view would be better if the the owner trimmed the trees between the house and the ocean view. The clothing dryer is missing the filter and doesn't work."
Spacious & tranquil waterfront hideaway on Muscongus Sound

Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer

9.8 out of 10, Exceptional, (17)
"This is a small backyard apartment a block away from downtown Wiscasset. The house met our needs. The bed was comfortable. The kitchen was small but with enough equipment to prepare simple meals. The house was in walking distance of shops and restaurants in Wiscasset. There was a grill and patio for those who wanted to cook outside. The was a washer and dryer available. "
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/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.
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Other property types in Pleasant Point

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very Good, (149)
"We got in very late. They had a lock box for us to get our keys after hours (texted us the code) and then checked on us the next day to make sure we made it safely. "
The price is SAR 414
SAR 492 total
includes taxes & fees
22 Jan - 23 Jan
Trade Winds on the Bay

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

9.8 out of 10, Exceptional, (38)
"I had an excellent visit. The kitchen was well stocked with utensils and small appliances. Everything was super clean; magazines and books were available (as well as good WiFi). I never turned the tv on as the view was spectacular. I wasn’t able to have an outdoor fire due to weather but everything was great. I hope to return. I look forward to doing more exploring as the area is beautiful. Also, very responsive with owners live next door. Thanks for offering up this quant little cabin for...
Cozy Cottage with spectacular salt water view / 3 Kayaks available/

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

9.8 out of 10, Exceptional, (59)
"Had an amazing stay at this charmer on the coast! Very clean, comfortable, and well cared for. Spent many hours just watching the ducks and birds enjoying the treats that come and go as the tides change. Great jumping off point to enjoy the beautiful coast of Maine! The only drawback is that the road is incredibly close to the house and the traffic noise is impossible to drown out, especially when trying to sleep in the second bedroom. Not ideal, but we would definitely return! "
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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