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Compare 359 Vacation Homes in Pleasant Point with updated reviews, rates, and availability.

Hidden Gem on Westport Island
10.0 out of 10, Exceptional, (97)
"Hidden gem is the perfect way to describe this amazing property at 19 Rocky Rd on beautiful Westport Island! We stayed 2 nights and wished we could have stayed longer! Next time! We feel very blessed by the whole experience! Thank you owners!"
Hidden Gem on Westport Island
2 Bedroom Close to Town Home
9.0 out of 10, Wonderful, (23)
"Brief stay in Thomaston with the family and the dog for a local celebration. This home is in a great location, close to everything. Clean, comfortable and well-equipped with everything we could need."
The price is SAR 563
SAR 1,146 total
includes taxes & fees
10 Oct - 11 Oct
2 Bedroom Close to Town Home
Waterfront Cottage on Tidal Cove with Dock
9.8 out of 10, Exceptional, (42)
"The property was very serene, laid back relaxing. We did plenty of exploring the surrounding areas. House was equipped better than others we have stayed at. We were very comfortable. "
Waterfront Cottage on Tidal Cove with Dock
THE BARN ON PASCAL... A lovely circa 1900 refurbished barn.
10.0 out of 10, Exceptional, (40)
"This place met all of our needs. Super convenient. Super clean and amazing in every way. We will be back"
THE BARN ON PASCAL... A lovely circa 1900 refurbished barn.
Oceanfront home on 6 acres with multi-level deck & spectacular view
9.8 out of 10, Exceptional, (8)
"Four friends since childhood gathered to celebrate our upcoming birthdays. "
Oceanfront home on 6 acres with multi-level deck & spectacular view
Cozy Cottage with Ocean Views and Dog-Friendly Charm
2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views and Dog-Friendly Charm
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
9.6 out of 10, Exceptional, (63)
"An immaculate well appointed cottage that was an absolute delight. Close to everything, including Colonial Pemaquid, Pemaquid Beach and the lighthouse."
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
9.4 out of 10, Exceptional, (47)
"We had a two-night stay. And since we were so close to the harbor, it made for easy walks to the points of interest nearby; easy walk to the harbor. We could see the harbor from out the windows. We cooked on the newer clean grill. You need to sign into your own Roku account to use the TV which we did to see the Olympics."
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Tranquil waterfront near Rockland, Camden-family and dog friendly
10.0 out of 10, Exceptional, (79)
"This beautiful and clean house was everything we were looking for"
Tranquil waterfront near Rockland, Camden-family and dog friendly
Oceanfront Adj. Resort +Lighthouse: Enjoy Beaches, Hikes, Quaint Shops &Lobster!
9.8 out of 10, Exceptional, (19)
"Clean, welcoming and well appointed. We couldn't have enjoyed our stay more. We are very familiar with the midcoast area and have stayed in this neighborhood before. This particular home was everything we hoped for."
Oceanfront Adj. Resort +Lighthouse: Enjoy Beaches, Hikes, Quaint Shops &Lobster!
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
10.0 out of 10, Exceptional, (3)
"Loved our stay. Walking distance to everything. Kids loved the kayaks & dock. We loved having coffee on the harbor every morning. Plenty of room for multiple families. "
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
10.0 out of 10, Exceptional, (107)
"Such a beautiful property! Our flight got a bit late and Alex and Siobhán were gracious and kind. They met us with the keys and went over the information needed. Because it was dark when we arrived, we were so amazed to see the beautiful views when we awoke. We were close to shops and amazing restaurants. I would definitely recommend!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Comfortable, Close to Town Home, with Oceanview.
9.8 out of 10, Exceptional, (61)
"We were attending a wedding at Saltwater Fields and this was perfect location close by. We loved it "
The price is SAR 732
SAR 1,417 total
includes taxes & fees
1 Nov - 2 Nov
Comfortable, Close to Town Home, with Oceanview.
Lovely Waterfront Owls Head Home w/ Own Beach
10.0 out of 10, Exceptional, (40)
"We really enjoyed our 5 nite stay in this beautiful waterfront home overlooking Monroe Island and beyond. The highlight of this home is the stunning view from every room, with even a glimpse of the Owl Head Light - look thru the sliding door & across the harbor. The home has been nicely updated with hardwood floors throughout and is very comfortably furnished, well equipped and maintained. We look forward to (many) return visits! Note for Verizon wireless users - reception in this area...
Lovely Waterfront Owls Head Home w/ Own Beach
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay
10.0 out of 10, Exceptional, (146)
"Loved the Coal Shack! Beautiful place with a great view! Perfectly situated. Easy to come and go. Shower was amazing! Would definitely recommend!"
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay
Quintessential Maine Oceanfront home
10.0 out of 10, Exceptional, (70)
"Had a wonderful time at the home. The views are just beautiful!"
Quintessential Maine Oceanfront home
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
5.6 out of 10, (5)
"The shared driveway was a challenge and the hike from the driveway to the house had was also a challenge. Additionally the window in one of the bathrooms did not work, the dishwasher was not secured and tilted when you put dishes in, one of the commodes ran constantly unless you jiggle. The kitchen garbage can is broken."
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays
10.0 out of 10, Exceptional, (10)
"This is a very nice, clean ranch style house that is a short walk from the harbor. It is very quiet and comfortable lodging. The area is extremely safe and very pleasant to go for walks. There is quite a bit to do in this area especially if you like lobster, rugged shorelines, foggy mornings, and smell of a fresh sea breeze. The only thing I would point out is that the living room and the kitchen are at different levels, so you have to be careful that you don't fall when walking from one to...
Mid-century modern walk to ocean, restaurants, and shops. Open for the holidays
Cottage in Edgecomb - Waterfront Holiday Getaway
10.0 out of 10, Exceptional, (22)
"The property inside, I would say, was renovated recently . Decorated very nicely and was organized. The queen bedroom was comfortable. My wife and I stayed for 4 nights going south to Portland and north to Arcadia and bar harbor and around Wiscasset Boothbay and Edgecomb the other days.Th only thing is the outside could use a deck and a walkway and a drive way. Nancy the host was very communicative and nice. Thanks for the use of your beautiful home!"
Cottage in Edgecomb - Waterfront Holiday Getaway
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
9.4 out of 10, Exceptional, (26)
"This is a great home with lots of room, natural light, comfortable bedrooms and a back deck we'd spend hours on in the evenings. Having a full bedroom and bathroom on the first floor and the two bedrooms and bathrooms upstairs also gave everyone privacy and downtime. The area is really quiet and walking distance from a path that runs alongside the water. The home is comfortable and roomy enough that being rained in for a day is no problem, and getting out to surrounding places is easy. "
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
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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
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/
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
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.