Pleasant Point Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Pleasant Point

Water view
Trade Winds on the Bay

Trade Winds on the Bay

3.5 star property
Rockland
8.4 out of 10, Very good, (321)
"Very nice place to stay. Staff helpful and friendly."
Canada
Dan
Trade Winds on the Bay
Microwave, oven, stovetop, dishwasher
Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston
10.0 out of 10, Exceptional, (1)
"We had a wonderful weeklong stay while visiting family and friends in the area. We had everything we needed, and even started saying "we're going home" when leaving family.We never waited longer than 10 minutes for a reply from Jason. Everything was new, efficient, clean, and comfortable. Situated close to route 1 was especially convenient. The bedrooms on the back of the unit were cozy and quiet for sleeping. Morning coffee on the deck in the chairs was a delight.We will definitely stay again,...
United States
Lauren A.
The price is HK$747
HK$1,637 total
includes taxes & fees
2 Jan - 3 Jan 2026
Bright 2-Bedroom Apartment Near Downtown Thomaston
Fridge, microwave, oven, stovetop
Firstmate by Rocky Coast Rentals

Firstmate by Rocky Coast Rentals

Boothbay Harbor
10.0 out of 10, Exceptional, (4)
"The house was perfect and the floor fans were great for sleepers that need white noise. "
United States
Josh L.
The price is HK$1,430
HK$3,998 total
includes taxes & fees
7 Dec - 8 Dec
Firstmate by Rocky Coast Rentals
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)
"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 HK$770
HK$2,172 total
includes taxes & fees
8 Dec - 9 Dec
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Terrace/patio
Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach

Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"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 HK$2,101
HK$4,479 total
includes taxes & fees
14 Dec - 15 Dec
Laughton House @ Pemaquid Beach
Marina
Rustic-Luxe Escape Near Town w/ Water Access, Kayaks, Games, Fire Pit & Peloton!

Rustic-Luxe Escape Near Town w/ Water Access, Kayaks, Games, Fire Pit & Peloton!

Friendship
10.0 out of 10, Exceptional, (4)
"This was a great old house with modern appliances. We enjoyed our stay and the peacefulness of the property. The host, Mia was thoughtful and very responsive when we had any questions. Thank you!"
United States
Jeff S.
The price is HK$2,179
HK$6,346 total
includes taxes & fees
7 Dec - 8 Dec
Rustic-Luxe Escape Near Town w/ Water Access, Kayaks, Games, Fire Pit & Peloton!
Microwave, oven, stovetop, dishwasher
Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor

2.0 star property
Rockport
The price is HK$616
HK$1,495 total
includes taxes & fees
17 Dec - 18 Dec
Romantic Coastal Escape near Harbor
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is HK$1,451
HK$3,710 total
includes taxes & fees
7 Dec - 8 Dec
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro
9.8 out of 10, Exceptional, (43)
"House was very clean and beautiful the beach and fishing are were lovely as well very nicecstay"
United States
Lori R.
The price is HK$1,044
HK$2,275 total
includes taxes & fees
9 Dec - 10 Dec
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Interior
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
9.6 out of 10, Exceptional, (84)
"This our second year and this property continues to be excellent. The proper is clean and comfortable and convenient to town or the each. The view from the porch is always stunning. The owner is very easy to work with. "
United States
Amy F.
The price is HK$1,226
HK$2,507 total
includes taxes & fees
7 Dec - 8 Dec
Comfortable, Close to Town Home, with Oceanview.
Fridge, microwave, oven, stovetop
Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views

Thomaston
9.4 out of 10, Exceptional, (29)
"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 HK$973
HK$2,138 total
includes taxes & fees
14 Dec - 15 Dec
Peaceful, Centrally Located Home with Seasonal River Views
Beach
Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub

Walpole
10.0 out of 10, Exceptional, (2)
"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 HK$2,311
HK$5,301 total
includes taxes & fees
7 Dec - 8 Dec
Pemaquid Escape | Curated Comfort + Hot Tub
Fridge, microwave, oven, stovetop
Charming Sheepscot Overlook Cottage

Charming Sheepscot Overlook Cottage

Edgecomb
10.0 out of 10, Exceptional, (10)
"Great location, great view, great house, great time"
United States
Carol P.
The price is HK$5,058
HK$8,933 total
includes taxes & fees
11 Dec - 12 Dec
Charming Sheepscot Overlook Cottage
TV
2 Bedroom Close to Town Home

2 Bedroom Close to Town Home

Thomaston
9.0 out of 10, Wonderful, (45)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is HK$805
HK$1,930 total
includes taxes & fees
14 Dec - 15 Dec
2 Bedroom Close to Town Home
1 bedroom, iron/ironing board, free WiFi
Solitude @ The Offshore House

Solitude @ The Offshore House

Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is HK$1,226
HK$2,342 total
includes taxes & fees
9 Dec - 10 Dec
Solitude @ The Offshore House
Outdoor dining
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

East Boothbay
10.0 out of 10, Exceptional, (46)
"Quiet and peaceful. Location was close to everything we had on our agenda. We highly recommend this as great place to stay!"
United States
Malinda E.
The price is HK$1,604
HK$3,903 total
includes taxes & fees
7 Dec - 8 Dec
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
Smart TV, books
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!

Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!

Boothbay Harbor
10.0 out of 10, Exceptional, (7)
"The property is beautiful and within walking distance to the main town area. The house has plenty of space for my family of 10 and the host went above and beyond with amenities."
United States
Leang C.
The price is HK$5,058
HK$6,650 total
includes taxes & fees
11 Dec - 12 Dec
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!
1 bedroom, iron/ironing board, WiFi, bed sheets
Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

2.0 star property
Newcastle
The price is HK$1,033
HK$1,296 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful Intown Studio ~ Walk to Shops & Dining
Outdoor dining
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

East Boothbay
10.0 out of 10, Exceptional, (20)
"Beautiful place, had everything we needed!"
United States
Kathy H.
The price is HK$1,604
HK$3,928 total
includes taxes & fees
16 Dec - 17 Dec
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Smart TV
Shipwright @ The Offshore House

Shipwright @ The Offshore House

Boothbay
9.4 out of 10, Exceptional, (13)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
The price is HK$1,226
HK$2,342 total
includes taxes & fees
9 Dec - 10 Dec
Shipwright @ The Offshore House
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
"The room was clean, I had trouble with the TV and the desk clerk was extremely helpful. He even came to our room and then he asked us if it was okay for him to enter the room to check out the TV. Definitely will be back.. "
Michael 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:

  • View our selection of featured holiday rentals in Pleasant Point
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  • Enter your travel dates to view the best deals on holiday rentals in Pleasant Point while they last

Look no further and take a look at our great range of rental properties in Pleasant Point!

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?

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.: This holiday home rental outside of Pleasant Point is located by the ocean, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Pleasant Point?

Choose from 8 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 La Verna Preserve. In the wider area, you’ll find Marshall Point Lighthouse and St. George River.

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.