Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Pleasant Point vacation rentals

Interior

Vacation Home in Thomaston

2 Bedroom Close to Town Home
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is ￥16,277
￥38,828 total
includes taxes & fees
Mar 6 - Mar 7
2 Bedroom Close to Town Home
Terrace/patio

Cabin in Boothbay

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
7.8 out of 10, Good, (7 reviews)
"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "
United States
Nichole W.
The price is ￥20,524
￥31,457 total
includes taxes & fees
Mar 6 - Mar 7
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Smart TV

Vacation Home in Thomaston

Peaceful, Centrally Located Home with Seasonal River Views
9.4 out of 10, Exceptional, (29 reviews)
"The house was clean and well stocked. It is is located in a cute little town."
United States
Candace L.
The price is ￥19,659
￥43,199 total
includes taxes & fees
Mar 8 - Mar 9
Peaceful, Centrally Located Home with Seasonal River Views
Lobby sitting area

Aparthotel in Rockland

Trade Winds on the Bay
3.5 star property
8.6 out of 10, Excellent, (351 reviews)
"Very nice place "
United States
Robert
Trade Winds on the Bay
Exterior

Vacation Home in Rockport

Romantic Coastal Escape near Harbor
The price is ￥15,620
￥34,052 total
includes taxes & fees
Mar 9 - Mar 10
Romantic Coastal Escape near Harbor
Interior

Vacation Home in Owls Head

Comfortable, Close to Town Home, with Oceanview.
9.6 out of 10, Exceptional, (86 reviews)
"Convenient location; host responsive; good towel supply. "
United States
Connie K.
The price is ￥27,601
￥55,971 total
includes taxes & fees
Mar 8 - Mar 9
Comfortable, Close to Town Home, with Oceanview.
Dining

Apartment in Newcastle

Peaceful Intown Studio ~ Walk to Shops & Dining
8.0 out of 10, Very Good, (3 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is ￥22,804
￥28,456 total
includes taxes & fees
Mar 5 - Mar 6
Peaceful Intown Studio ~ Walk to Shops & Dining
Fridge, microwave, oven, stovetop

Apartment in East Boothbay

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
10.0 out of 10, Exceptional, (46 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is ￥28,167
￥73,901 total
includes taxes & fees
Mar 5 - Mar 6
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
Fridge, microwave, oven, stovetop

Apartment in East Boothbay

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
10.0 out of 10, Exceptional, (22 reviews)
"The entire process was seamless. The home is adorable and was perfect for our weekend in Boothbay Harbour."
United States
Leslie B.
The price is ￥38,924
￥87,170 total
includes taxes & fees
Mar 5 - Mar 6
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Property grounds

Vacation Home in Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and convenient location. Super comfortable beds and living room furniture. Host was very quick to clean up the snow that fell overnight!"
United States
tom w.
The price is ￥19,659
￥39,085 total
includes taxes & fees
Mar 5 - Mar 6
Bright 2-Bedroom Apartment Near Downtown Thomaston
WiFi

Vacation Home in Union

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is ￥31,454
￥44,489 total
includes taxes & fees
Apr 1 - Apr 2
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Interior

Mobile Home in Union

Come Spring Farm Airstream , Lake & farm animals
10.0 out of 10, Exceptional, (1 review)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is ￥31,454
￥46,799 total
includes taxes & fees
Apr 1 - Apr 2
Come Spring Farm Airstream , Lake & farm animals
Property grounds

Cabin in Boothbay

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is ￥52,371
￥70,798 total
includes taxes & fees
Mar 5 - Mar 6
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Beach

Vacation Home in Walpole

Pemaquid Escape | Curated Comfort + Hot Tub
10.0 out of 10, Exceptional, (2 reviews)
"This was a last minute booking for our family as we had a basketball tournament, there were 8 of us including 3 children. This was the most kid friendly house we have stayed in! It was so well stocked for the entire family. The house was meticulously cleaned and the hosts were very responsive to any questions! "
United States
Melissa L.
The price is ￥46,709
￥107,132 total
includes taxes & fees
Mar 5 - Mar 6
Pemaquid Escape | Curated Comfort + Hot Tub
WiFi

Vacation Home in Union

Come Spring Farm Glamping Dome 2
6.8 out of 10, (3 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is ￥27,522
￥39,517 total
includes taxes & fees
Apr 1 - Apr 2
Come Spring Farm Glamping Dome 2
Terrace/patio

Cabin in Boothbay

Newly Renovated Cozy Cove Cabin at White Anchor Inn
8.4 out of 10, Very Good, (6 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is ￥52,371
￥68,741 total
includes taxes & fees
Mar 11 - Mar 12
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Exterior

Cottage in Edgecomb

Charming Sheepscot Overlook Cottage
10.0 out of 10, Exceptional, (10 reviews)
"Great location, great view, great house, great time"
United States
Carol P.
The price is ￥102,226
￥186,367 total
includes taxes & fees
Mar 5 - Mar 6
Charming Sheepscot Overlook Cottage
Terrace/patio

Cabin in Boothbay

Renovated The Driftwood Cabin at White Anchor Inn
8.0 out of 10, Very Good, (2 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is ￥52,371
￥71,655 total
includes taxes & fees
Mar 10 - Mar 11
Renovated The Driftwood Cabin at White Anchor Inn
Outdoor dining

Apartment in Boothbay Harbor

2-story apartment steps from the harbor & downtown
6.0 out of 10, (1 review)
"The apartment was quite cozy and clean. However, winter in Maine is unpredictable and must prepare for it. Huge liability risk not to have lighted parking area at night, walkways too narrow of snow and not well lit or shoveled."
United States
Anonymous traveler
The price is ￥47,181
￥121,763 total
includes taxes & fees
Mar 5 - Mar 6
2-story apartment steps from the harbor & downtown
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

Trade Winds on the Bay

Trade Winds on the Bay

10/10 Excellent
"This is a perfect location in downtown Rockland. The rooms and staff are gracious & efficient."
Nancy 1-night trip
Posted 2 days ago
Trade Winds on the Bay

Find out more about Pleasant Point

Search for holiday rentals in Pleasant Point on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasant Point using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Pleasant Point?

Yes, we offer vacation rentals close to popular local attractions in Pleasant Point, or you can choose a more remote option if you're looking for relaxation.

What's the top vacation rental in Pleasant Point?

Peaceful Lake waterfront! Full Kitchen! Heat&AC! 5min to town, 8min to Garden!: Visitors like this Pleasant Point vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Pleasant Point?

Choose from 8 Expedia vacation rentals in Pleasant Point for a memorable vacation.

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 larger area, you’ll find Marshall Point Lighthouse and Maine Coastal Islands National Wildlife Refuge.

What’s a vacation rental in Pleasant Point like?

Vacation rentals are private properties where you can stay for a couple of days or more in Pleasant Point. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.