Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Pleasant Point vacation rentals

Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (333 reviews)
"Very nice place "
United States
Robert
Trade Winds on the Bay
Smart TV

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (29 reviews)
"Amazing little house tucked away close to the river. It was very clean and nicely furnished. I had a great time staying here and it was very close to downtown Thomaston."
United States
Avery W.
The price is ￥19,765
￥43,260 total
includes taxes & fees
Jan 19 - Jan 20
Peaceful, Centrally Located Home with Seasonal River Views
Property grounds

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Boothbay
10.0 out of 10, Exceptional, (1 review)
"This efficiency apartment was nicely furnished with everything needed and conveniently located on the main road into Boothbay Harbor. The host was generous and accommodating. The region is fun to visit!"
United States
Mary D.
The price is ￥15,654
￥44,122 total
includes taxes & fees
Jan 19 - Jan 20
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Terrace/patio

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
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 ￥20,635
￥31,628 total
includes taxes & fees
Jan 18 - Jan 19
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
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 ￥15,180
￥33,781 total
includes taxes & fees
Jan 18 - Jan 19
Bright 2-Bedroom Apartment Near Downtown Thomaston
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (45 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is ￥16,365
￥39,038 total
includes taxes & fees
Jan 21 - Jan 22
2 Bedroom Close to Town Home
Interior

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (85 reviews)
"Convenient location; host responsive; good towel supply. "
United States
Connie K.
The price is ￥24,904
￥52,654 total
includes taxes & fees
Jan 20 - Jan 21
Comfortable, Close to Town Home, with Oceanview.
Smart TV

Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach
Pemaquid Beach
10.0 out of 10, Exceptional, (8 reviews)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is ￥41,839
￥86,451 total
includes taxes & fees
Jan 18 - Jan 19
Laughton House @ Pemaquid Beach
Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
Newcastle
6.0 out of 10, (1 review)
The price is ￥18,342
￥23,440 total
includes taxes & fees
Jan 18 - Jan 19
Peaceful Intown Studio ~ Walk to Shops & Dining
Property grounds

Pet friendly Waterfront Condo Sunset Views

Pet friendly Waterfront Condo Sunset Views
2.0 star property
Edgecomb
The price is ￥27,956
￥34,780 total
includes taxes & fees
Jan 18 - Jan 19
Pet friendly Waterfront Condo Sunset Views
Beach

Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
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.
Pemaquid Escape | Curated Comfort + Hot Tub
Property grounds

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
2.0 star property
Boothbay
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 ￥52,654
￥70,836 total
includes taxes & fees
Jan 18 - Jan 19
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Exterior

The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
The price is ￥139,936
￥204,753 total
includes taxes & fees
Jan 18 - Jan 19
The Entire Waldoboro Inn
Terrace/patio

Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
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 ￥52,654
￥70,836 total
includes taxes & fees
Jan 24 - Jan 25
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Terrace/patio

Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
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 ￥52,654
￥71,870 total
includes taxes & fees
Jan 24 - Jan 25
Renovated The Driftwood Cabin at White Anchor Inn
Outdoor dining

2-story apartment steps from the harbor & downtown

2-story apartment steps from the harbor & downtown
Boothbay Harbor
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 ￥47,436
￥120,198 total
includes taxes & fees
Jan 18 - Jan 19
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

Rockport Harbor Hotel

Rockport Harbor Hotel

10/10 Excellent
"Wonderful! Check in was super easy and staff was extremely helpful, attentive and friendly. Room was amazing!"
Melissa 1-night trip
Posted 4 days ago
Rockport Harbor Hotel

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?

8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat! : 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 Tenants Harbor Marina.

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.