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Vacation Homes in Pleasant Point

Our top choices for Pleasant Point vacation homes

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

9.6 out of 10, Exceptional, (39)
"Very clean and had everything we needed for a nice long weekend with our pup in Boothbay Harbor"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

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."
Comfortable, Close to Town Home, with Oceanview.

2 Bedroom Close to Town Home

9.2 out of 10, Wonderful, (37)
"Very clean and nice property as advertised."
2 Bedroom Close to Town Home

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (32)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is AED 625
AED 1,238 total
includes taxes & fees
10 Sep - 11 Sep
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Oceanview Bungalow Style Home in Owls Head

9.8 out of 10, Exceptional, (60)
"Great property for family to visit Maine. Thank you!"
Oceanview Bungalow Style Home in Owls Head

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

10.0 out of 10, Exceptional, (27)
"Nice and quiet location but only 10-15 minute ride to downtown and local area attractions."
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

9.6 out of 10, Exceptional, (33)
"The proximity to our activities and space for our family was perfect."
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

Beautiful River-View Retreat | Home Office | Walk 5 MInutes to Main Street

9.6 out of 10, Exceptional, (18)
"Nice house, close to great dining and only 5 min to a great grocery store"
Beautiful River-View Retreat | Home Office | Walk 5 MInutes to Main Street

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

Waterfront home with beautiful bay views - near shops & dining

9.4 out of 10, Exceptional, (27)
"Very clean, great location, great amenities. Hiy recommend this location"
Waterfront home with beautiful bay views - near shops & dining

Lakeside Retreat in Boothbay, Maine with Private Dock & Scenic Views

9.6 out of 10, Exceptional, (9)
Lakeside Retreat in Boothbay, Maine with Private Dock & Scenic Views

Come Spring Farm Glamping Dome 2

The price is AED 735
AED 1,039 total
includes taxes & fees
4 Sep - 5 Sep
Come Spring Farm Glamping Dome 2

Breathtaking views, total relaxation, do as much or as little as you choose

9.8 out of 10, Exceptional, (86)
"My wife and I enjoyed our stay in Owls Head. It was perfect for us. Hiking trails nearby and good seafood not far away"
Breathtaking views, total relaxation, do as much or as little as you choose

Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town

8.2 out of 10, Very Good, (23)
"Wonderful stay!"
Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town

Single-family home situated on the waterfront in the beautiful midcoast Maine

8.8 out of 10, Excellent, (3)
"Huddle House was a perfect fit for my family when visiting the area for a family reunion. It was clean, comfortable, and well stocked. We loved that it was an older home with a lot of character."
Single-family home situated on the waterfront in the beautiful midcoast Maine

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

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

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!

Lovely Waterfront Owls Head Home w/ Own Beach

10.0 out of 10, Exceptional, (59)
" The views were amazing , The house was really nice - spent three days and loved our stay "
Lovely Waterfront Owls Head Home w/ Own Beach

25% OFF 2025 LABOR DAY WE+AUG, SEPT, OCT Days Oceanfront Adj. Resort +Lighthouse

10.0 out of 10, Exceptional, (25)
"Awesome area! Beautiful golf resort right beside us. We had everything we needed and more. Host was very helpful and responsive I plan to come back for sure!!!"
25% OFF 2025 LABOR DAY WE+AUG, SEPT, OCT Days Oceanfront Adj. Resort +Lighthouse
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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Top Pleasant Point Hotel Reviews