Pleasant Point Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Vacation Rentals in Pleasant Point

Water view
Trade Winds on the Bay

Aparthotel in Rockland

3.5 star property
8.4 out of 10, Very Good, (319)
"Very nice place to stay. Staff helpful and friendly."
Canada
Dan
$99 nightly
The price is $108
Dec 15 - Dec 16
Total with taxes and fees
Trade Winds on the Bay
Microwave, oven, stovetop, dishwasher
Bright 2-Bedroom Apartment Near Downtown Thomaston

Vacation Home in 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.
$193 nightly
The price is $210
Dec 5 - Dec 6
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
Microwave, oven, stovetop, dishwasher
Romantic Coastal Escape near Harbor

Vacation Home in Rockport

2.0 star property
$176 nightly
The price is $192
Dec 10 - Dec 11
Total with taxes and fees
Romantic Coastal Escape near Harbor
Property grounds
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Apartment in 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.
$255 nightly
The price is $278
Dec 5 - Dec 6
Total with taxes and fees
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Interior
Comfortable, Close to Town Home, with Oceanview.

Vacation Home in 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.
$296 nightly
The price is $322
Dec 5 - Dec 6
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Fridge, microwave, oven, stovetop
Firstmate by Rocky Coast Rentals

Apartment in 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.
$493 nightly
The price is $515
Dec 5 - Dec 6
Total with taxes and fees
Firstmate by Rocky Coast Rentals
1 bedroom, iron/ironing board, WiFi, bed sheets
Peaceful Intown Studio ~ Walk to Shops & Dining

Apartment in Newcastle

2.0 star property
$153 nightly
The price is $167
Dec 7 - Dec 8
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Vacation Home in South Bristol

9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
$437 nightly
The price is $477
Dec 7 - Dec 8
Total with taxes and fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Vacation Home in 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.
$268 nightly
The price is $292
Dec 9 - Dec 10
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
1 bedroom, iron/ironing board, free WiFi
Solitude @ The Offshore House

Condo in 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.
$282 nightly
The price is $299
Dec 5 - Dec 6
Total with taxes and fees
Solitude @ The Offshore House
Outdoor dining
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Apartment in 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.
$460 nightly
The price is $502
Dec 6 - Dec 7
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
TV
2 Bedroom Close to Town Home

Vacation Home in 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.
$228 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
2 Bedroom Close to Town Home
Marina
Rustic-Luxe Escape Near Town w/ Water Access, Kayaks, Games, Fire Pit & Peloton!

Vacation Home in 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.
$786 nightly
The price is $857
Dec 7 - Dec 8
Total with taxes and fees
Rustic-Luxe Escape Near Town w/ Water Access, Kayaks, Games, Fire Pit & Peloton!
Fridge, microwave, oven, stovetop
Peaceful, Centrally Located Home with Seasonal River Views

Vacation Home in 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.
$252 nightly
The price is $275
Dec 5 - Dec 6
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Smart TV
Shipwright @ The Offshore House

Condo in Boothbay

9.4 out of 10, Exceptional, (13)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
$282 nightly
The price is $299
Dec 5 - Dec 6
Total with taxes and fees
Shipwright @ The Offshore House
Beach
Pemaquid Escape | Curated Comfort + Hot Tub

Vacation Home in 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.
$589 nightly
The price is $642
Dec 8 - Dec 9
Total with taxes and fees
Pemaquid Escape | Curated Comfort + Hot Tub
Outdoor dining
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Apartment in East Boothbay

10.0 out of 10, Exceptional, (20)
"Beautiful place, had everything we needed!"
United States
Kathy H.
$461 nightly
The price is $503
Dec 5 - Dec 6
Total with taxes and fees
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Terrace/patio
Laughton House @ Pemaquid Beach

Vacation Home in 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.
$528 nightly
The price is $576
Dec 13 - Dec 14
Total with taxes and fees
Laughton House @ Pemaquid Beach
Terrace/patio
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cabin in Boothbay

7.8 out of 10, Good, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
$183 nightly
The price is $199
Dec 5 - Dec 6
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Exterior
Luxury Yurt at Seaside Farm in Friendship

Vacation Home in Friendship

2.0 star property
$895 nightly
The price is $976
Dec 5 - Dec 6
Total with taxes and fees
Luxury Yurt at Seaside Farm in Friendship
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasant Point Hotel Reviews

The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

10/10 Excellent
"Everything was spotless. The pool and hot tub seemed like they were brand new. The breakfast was amazing (I frankly didn’t believe the reviews that said so, but it’s true!). We will be back!!"
Kirk 1-night trip
Posted 21 hours ago
The Country Inn at Camden Rockport

Find out more about Pleasant Point

Everything you need to know about Pleasant Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Point vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Point vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Point. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasant Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasant Point rentals

At Expedia, we put the best Pleasant Point vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasant Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Point vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.: Visitors like this Pleasant Point vacation home rental. It is located by the ocean and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 La Verna Preserve. In the larger area, you’ll find Marshall Point Lighthouse and St. George River.

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.