Default HTG hotel image

Pleasant Point Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Pleasant Point holiday rentals

Exterior

Applecroft Cabin No. 1 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 1 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is NZ$292
includes taxes & fees
8 July - 9 July
Applecroft Cabin No. 1 - Modern off-grid cabin deep in the woods.
Interior

Damariscotta Lakefront Cottage perfect for a relaxing getaway

Damariscotta Lakefront Cottage perfect for a relaxing getaway
Jefferson
The price is NZ$1,248
includes taxes & fees
2 Aug - 3 Aug
Damariscotta Lakefront Cottage perfect for a relaxing getaway
Property grounds

Oceanfront Maine Cottage, Private Shoreline, Sunset Views, Near Lighthouse.

Oceanfront Maine Cottage, Private Shoreline, Sunset Views, Near Lighthouse.
Owls Head
The price is NZ$959
includes taxes & fees
12 July - 13 July
Oceanfront Maine Cottage, Private Shoreline, Sunset Views, Near Lighthouse.
Property grounds

Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (64 reviews)
"Perfect home away from home. Very well stocked kitchen, the beds were very comfy and everything was just overall cozy. Such a serene location. We will definitely stay again next time we come to visit our grandkids. "
United States
Tina B.
The price is NZ$991
includes taxes & fees
13 July - 14 July
Oceanview Bungalow Style Home in Owls Head
Interior

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (93 reviews)
"Yes it was a great place the view was great and it was pet friwndly"
United States
Edward L.
The price is NZ$784
includes taxes & fees
13 July - 14 July
Comfortable, Close to Town Home, with Oceanview.
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (2 reviews)
"My family of four greatly enjoyed our stay at this property. Location was very convenient to explore the mid coast towns of Rockport, Rockland, and Camden and all of their beautiful harbors. Having two bedrooms worked well for us along with the living room and a large open kitchen and full bathroom. The private entrance that leads up to the open top floor was easy to manage and appreciated. The quiet street was frequented by wild turkeys that roamed the yard and crossed the street on two...
United States
Christopher H.
The price is NZ$559
includes taxes & fees
13 July - 14 July
Romantic Coastal Escape near Harbor
Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (426 reviews)
"Everything was great and the location was amazing. Right in the arts district and surrounded by interesting shops, amazing eats and coffee & right on the harbor."
United States
Gerald
Trade Winds on the Bay
1 bedroom, free WiFi, bed sheets

Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (25 reviews)
"Very comfortable, well stocked and quiet."
United States
Lucy F.
The price is NZ$312
includes taxes & fees
8 July - 9 July
Simplicity-Just what you need! STR24-20
Smart TV

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (47 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is NZ$602
includes taxes & fees
8 July - 9 July
2 Bedroom Close to Town Home
Fridge, microwave, oven, stovetop

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (31 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
The price is NZ$835
includes taxes & fees
19 July - 20 July
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.6 out of 10, Exceptional, (5 reviews)
"Host was fast in responding to all questions and concerns. Location was good for being close to all shopping and eating. "
United States
Kim W.
The price is NZ$529
includes taxes & fees
8 July - 9 July
Bright 2-Bedroom Apartment Near Downtown Thomaston
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, (33 reviews)
"Great place at a great price! We look forward to staying there again. "
United States
Stephen H.
The price is NZ$589
includes taxes & fees
8 July - 9 July
Peaceful, Centrally Located Home with Seasonal River Views
Exterior

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Camden
The price is NZ$576
includes taxes & fees
8 July - 9 July
Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Property grounds

Luxury Lakefront Cabin in Hope - Close to Camden & Rockland

Luxury Lakefront Cabin in Hope - Close to Camden & Rockland
Hope
10.0 out of 10, Exceptional, (1 review)
"Jen was very communicative…responding in minutes! The cabin was lovely and very comfortable. Our youngest son spent the afternoon and following morning fishing off the dock and loved the s’more fixings. My husband took out the kayak and just relaxed by reading and taking in the tranquil setting. Our oldest loved hanging in his nook. I took advantage of the washer/dryer but also enjoyed a glass of wine and the old school records. The beds were very comfortable, and the master bedroom was...
United States
Lauren E.
The price is NZ$1,811
includes taxes & fees
19 July - 20 July
Luxury Lakefront Cabin in Hope - Close to Camden & Rockland
Terrace/patio

Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is NZ$1,198
includes taxes & fees
8 July - 9 July
Luxury Yurt at Seaside Farm in Friendship
Interior

Unique ISLAND Living off the grid -Waterfront cottage

Unique ISLAND Living off the grid -Waterfront cottage
Friendship
10.0 out of 10, Exceptional, (27 reviews)
"We love coming here and once again we had a wonderful week! The outside world melts away when you’re on Friendship Long Island."
United States
Cheryl C.
The price is NZ$837
includes taxes & fees
4 Aug - 5 Aug
Unique ISLAND Living off the grid -Waterfront cottage
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (18 reviews)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
The price is NZ$481
includes taxes & fees
9 July - 10 July
Dome 1 - Luxury Dome at Come Spring Farm
WiFi

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.4 out of 10, Very good, (9 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is NZ$484
includes taxes & fees
15 July - 16 July
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Interior

Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
10.0 out of 10, Exceptional, (3 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is NZ$561
includes taxes & fees
26 July - 27 July
Come Spring Farm Airstream , Lake & farm animals
WiFi

Come Spring Farm Glamping Dome 2

Come Spring Farm Glamping Dome 2
Union
5.6 out of 10, (4 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 NZ$460
includes taxes & fees
8 July - 9 July
Come Spring Farm Glamping Dome 2
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

Glen Cove Inn & Suites

Glen Cove Inn & Suites

10/10 Excellent
"The woman at the front desk was such a ray of light, both in the afternoon and in the morning. She was smiling and genuinely pleasant and helpful. The property is well maintained and it looked like they really took pride is keeping it up. The beds were comfortable and the water pressure and temp as they should be. Breakfast was really nice, especially for being listed as continental. There were muffins, bagels, hard boiled eggs, cereal, oatmeal, juices, and a waffle iron. We’d stay again if ever in the area."
Angela 1-night trip
Posted 16 hours ago
Glen Cove Inn & Suites

Find out more about Pleasant Point

Everything you need to know about Pleasant Point holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pleasant Point holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Point holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Point holiday rentals we have selected for you start as low as NZ$305 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pleasant Point rentals

At Expedia, we put the best Pleasant Point holiday 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 holiday.

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. 

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?

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: This holiday home rental outside of Pleasant Point is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Pleasant Point?

Choose from 10 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 Penobscot Marine Museum, or get out into nature at a spot like St. George River. In the wider area, you’ll find Marshall Point Lighthouse and Maine Coastal Islands National Wildlife Refuge.

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.