Pleasant Point Holiday Rentals

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Holiday Rentals in Pleasant Point

Trade Winds on the Bay
3.0 star property
7.8 out of 10, Good, (98)
"I have stayed at the Tradewinds many times and it is very conveniently located with a great view of the harbor. It also now has a nice little coffee bar right in the hotel. "
The price is NZ$329
includes taxes & fees
25 Sept - 26 Sept
Trade Winds on the Bay
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
9.8 out of 10, Exceptional, (35)
"The cabin was nice and cozy . It overlooked the bay and the working lobster boats. Very idyllic. The owner's dogs were friendly and enjoyed playing with my dog. The neighborhood was safe and I enjoyed walking to the landing up the street."
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
A Charming Waterfront Cottage with Touches of Elegance
10.0 out of 10, Exceptional, (92)
"Comfortable, cozy, well-equipped home with gorgeous water views, and water access. The host was most delightful. "
A Charming Waterfront Cottage with Touches of Elegance
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
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
9.4 out of 10, Exceptional, (74)
"We enjoyed the tranquility of the cottage and we appreciated the antiques connecting the cottage to the past/ history of the area. No issues with our stay. Location was good; the drive to daily activities not tremendous. Loved the village, and the people were so friendly. Great escape from every day life."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
10.0 out of 10, Exceptional, (104)
"Convenient location and you can’t beat the view. Lots of little extras (especially appreciated the chocolate). Felt cozy. Kitchen had all of the essential equipment and salt and pepper. Walk to the water was easy and closer than expected. Would stay here again."
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
‘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
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
8.8 out of 10, Excellent, (31)
"The title and description are spot on, this is a vintage home with every amenity we needed for a long weekend exploring Damariscotta and Boothbay Harbor. We only needed 3 bedrooms, so did not use the bunk beds tucked into the first floor alcove, and planned to spend most of our time out & about. It was a perfect location for us."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
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
Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas
8.4 out of 10, Very good, (19)
"We were celebrating my sister getting married soon. Overall it was a great experience and a comfortable space for us all to enjoy. Not too far from downtown Boothbay Harbor while also having privacy. Check in was delayed by an hour due to the property still being cleaned from the previous guests and the trash outside was overflowing. Other than that, which wasn’t super impactful just some mild inconveniences, it was a great stay and I would recommend it to anyone with a larger group."
Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
9.6 out of 10, Exceptional, (13)
"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
Lakefront cottage with dock, screened porch, & Island in Biscay Pond
8.8 out of 10, Excellent, (18)
"This is the perfect Maine camp! Clean, comfortable and cute."
Lakefront cottage with dock, screened porch, & Island in Biscay Pond
East Boothbay Waterfront One room Condo.Waterview from in side this room
9.8 out of 10, Exceptional, (125)
"This has been our 2nd stay at this location. Everything was great ( very clean & quiet) and April was very accommodating. Would stay here again. "
East Boothbay Waterfront One room Condo.Waterview from in side this room
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
9.0 out of 10, Wonderful, (36)
"Great location, right in downtown Wiscassett. Several restaurants within walking distance and a short drive to Damariscotta and Pemaquid Lighthouse. "
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
9.6 out of 10, Exceptional, (63)
"We had a two night stay in beautiful New Harbor. Close to the beach, sights, and restaurants. House was very clean & well appointed kitchen. Loved sitting out in the deck for lunch and late afternoon sun. Just need to mention it is 3 stairs down to Kitchen, back bedroom, & bath if there are accessibility issues. "
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
9.8 out of 10, Exceptional, (63)
"Somehow, this place is both a cabin in the woods and a mountaintop aerie. We all had a great stay for a long weekend getaway to the area. The location was very convenient to Camden/Rockport/Rockland with all that area had to offer: great shopping, restaurants, and hikes. We were there with three dogs and were able to walk them on the property on the driveway and surrounding grass area. The hosts were wonderful.They responded quickly to questions and concerns and went above and beyond...
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
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
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
10.0 out of 10, Exceptional, (20)
"Very nice place The only thing that should be do is have them clean the window sills I also live in the woods and have the same problems"
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
8.2 out of 10, Very good, (38)
"We enjoyed our stay here very much. Loved how we could easily walk to Boothbay. Access to the kayaks was a huge plus too. If there was one bit of advice I could offer, it would be to reduce the amount of furniture in the cabin. I believe there were 15 chairs within."
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
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Other types of properties in Pleasant Point you may be interested in

The Country Inn at Camden Rockport
2.5 star property
9.4 out of 10, Exceptional, (1000)
"The room was spacious and in great condition. The pool and hot tub were welcome relief after a long day. Only issue was that the elevator was not working."
The price is NZ$348
includes taxes & fees
13 Oct - 14 Oct
The Country Inn at Camden Rockport
Flagship Inn and Suites
2.5 star property
8.2 out of 10, Very good, (1001)
"It's great for a short stay"
The price is NZ$247
includes taxes & fees
22 Sept - 23 Sept
Flagship Inn and Suites
Tugboat Inn
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Overlooks marina with balcony. Close to dining options. A pleasant stay."
The price is NZ$299
includes taxes & fees
14 Oct - 15 Oct
Tugboat Inn
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.

Frequently asked questions

Can I find holiday rentals in Pleasant Point?

Yes, there are holiday rentals close to the most popular sights in Pleasant Point, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pleasant Point has to offer?

Slow Down & Go Back in Time-Relax Completely in Our Maine Home: This holiday home rental outside of Pleasant Point is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Pleasant Point?

Choose from 9 Expedia holiday rentals in Pleasant Point for a memorable holiday.

What’s there to see and do in Pleasant Point?

Explore the area and family-friendly sights such as Maine State Prison Store, or get out into nature at a spot like St. George River. In the wider area, you’ll find Marshall Point Lighthouse and Owls Head Transportation Museum.

What’s a holiday rental in Pleasant Point like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pleasant Point. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.