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

Aparthotel in Rockland

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

Vacation Home in Thomaston

Peaceful, Centrally Located Home with Seasonal River Views
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
￥43,432 total
includes taxes & fees
Jan 20 - Jan 21
Peaceful, Centrally Located Home with Seasonal River Views
Property grounds

Apartment in Boothbay

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

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 ￥20,635
￥31,628 total
includes taxes & fees
Jan 18 - Jan 19
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
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 ￥18,974
￥38,434 total
includes taxes & fees
Feb 4 - Feb 5
Bright 2-Bedroom Apartment Near Downtown Thomaston
Interior

Vacation Home in Thomaston

2 Bedroom Close to Town Home
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

Vacation Home in Owls Head

Comfortable, Close to Town Home, with Oceanview.
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

Vacation Home in Pemaquid Beach

Laughton House @ 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

Apartment in Newcastle

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
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
Dining

Apartment in Edgecomb

Pet friendly Waterfront condo
2.0 star property
The price is ￥27,956
￥34,780 total
includes taxes & fees
Jan 18 - Jan 19
Pet friendly Waterfront condo
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 ￥47,101
￥108,031 total
includes taxes & fees
Jan 18 - Jan 19
Pemaquid Escape | Curated Comfort + Hot Tub
Property grounds

Cabin in Boothbay

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
2.0 star property
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

Vacation Home in Waldoboro

The Entire Waldoboro Inn
The Entire Waldoboro Inn
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 ￥52,654
￥70,836 total
includes taxes & fees
Jan 24 - Jan 25
Newly Renovated Cozy Cove Cabin at White Anchor Inn
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 ￥52,654
￥71,870 total
includes taxes & fees
Jan 24 - Jan 25
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 ￥47,436
￥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:

  • View our selection of featured holiday rentals in Pleasant Point
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Look no further and take a look at our great range of rental properties in Pleasant Point!

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.