Pleasant Point Holiday Rentals from NZ$254: Search Short-Term Rentals

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Our top choices for Pleasant Point holiday rentals

A spacious room with a dining table, chairs, and a sofa. There are large windows offering a view of the outdoors.

1. Bee Hive Cottage, Romantic Maine Waterfront Cottag

Cushing

includes taxes & fees

20 Sept - 21 Sept

2. Trade Winds on the Bay

Rockland

Lawrence

includes taxes & fees

8 Sept - 9 Sept

A wooden deck with two blue Adirondack chairs, surrounded by white flowers and trees.

3. Luxury Yurt at Seaside Farm in Friendship

Friendship

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a round rug.

4. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Waldoboro

Deborah

includes taxes & fees

9 Sept - 10 Sept

A wooden deck with Adirondack chairs and a grill.

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

Thomaston

Alexis H.

includes taxes & fees

8 Sept - 9 Sept

A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

6. Peaceful, Centrally Located Home with Seasonal River Views

Thomaston

includes taxes & fees

29 Sept - 30 Sept

A room with a large window offering a view of a snowy landscape and a body of water.

7. Comfortable, Close to Town Home, with Oceanview.

Owls Head

Rich W.

includes taxes & fees

8 Sept - 9 Sept

A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

8. 2 Bedroom Close to Town Home

Thomaston

Brianna M.

includes taxes & fees

29 Sept - 30 Sept

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Top Pleasant Point Hotel Reviews

Rockland Harbor Hotel

8/10 Good

"Nice place, clean and easy access to main street dining and shopping. Major complaint was the balcony had a big puddle of water due to the air conditioner leaking and no proper drainage - it was a mess."

Bluebird Ocean Point Inn

10/10 Excellent

"This is a lovely hotel with a wonderful restaurant. We had a gorgeous view of the ocean from our window in our room and also from the dinner table at the restaurant. The people working there were very attentive and helpful. There were some people having a loud party outside, singing and laughing. We closed the window and had a peaceful night. The only thing that wasn't great was the coffee at the restaurant in the morning!! Not a big deal. Had a great stay! Would definitely stay there again!"

Ledges by the Bay

8/10 Good

"A nicely located hotel/motel with a view of the Bay for every room, as far as I know. Reasonable prices, mediocre breakfast; the one thing I really wanted was a screen in the sliding glass door so that I could enjoy the air coming from the bay. It's easy to guess that these oversized screens were broken again and again and management finally gave up. I would still like a solution to that problem."

Topside Inn

10/10 Excellent

"This was by far our best Boothbay experience in over 28 years of vacationing there. Admittedly, this was a splurge we had to save up for, but it was worth every penny. Greg (the general manager) was exceptional in his efforts to welcome every guest and make sure they had what they need to have a wonderful stay. Housekeeping staff were ready to respond with smiles and "hellos." The evening bartender was top notch for her pours and for keeping on top of guests' needs. The morning breakfast crew were beyond compare in their agility in staying on top of clearing dishes and refreshing buffet components. ...And the CHEF! Gourmet breakfasts that are picture-worthy and 5-star in quality and taste. The property itself provides amazing views and comfortable furniture throughout, and it's worth mentioning the hospitality room that provides coffee, tea, sodas and light snacks 24-7. This all sounds too good to be true...but it is. We are already strategizing when/how to get back there. The only "catch" worth mentioning is because this wonderful inn is located on a hill overlooking the harbor, there is (obviously) a hill to drive or walk up to get to it. It is literally a five-minute walk to the downtown harbor area, which is perfect for shopping, sea excursions, and dining options. Getting back up takes a little bit of effort, but it is doable. My husband and I are obese and managed the walk up and down several times daily and have no qualms about returning to do that again"

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$254 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?

3-bdrm house in beautiful Boothbay! A perfect location for relaxing getaways!: This holiday home rental outside of Pleasant Point offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings.

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.

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Check prices for these dates

Our top choices for Pleasant Point holiday rentals

1. Bee Hive Cottage, Romantic Maine Waterfront Cottag

2. Trade Winds on the Bay

3. Luxury Yurt at Seaside Farm in Friendship

4. Near Lakes, Bay & Trails! Historic Waldoboro Gem

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

6. Peaceful, Centrally Located Home with Seasonal River Views

7. Comfortable, Close to Town Home, with Oceanview.

8. 2 Bedroom Close to Town Home

9. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

10. Near Lakes, Bay & Trails! Historic Waldoboro Gem

11. Simplicity-Just what you need! STR24-20

12. Peaceful Intown Studio ~ Walk to Shops & Dining

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

14. Cheerful Cottage with Loft 9

15. Tiny Cottage Near Everything 10

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

17. Spacious 1 Bedroom Close to Everything 4

18. Spacious 1 Bedroom Cottage Close to Everything 3

19. Oceanview Bungalow Style Home in Owls Head

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Find holiday rentals that suit your style

Top Pleasant Point Hotel Reviews

Rockland Harbor Hotel

Trade Winds on the Bay

Bluebird Ocean Point Inn

Tugboat Inn

Fishermans Wharf Inn

Smuggler's Cove Inn

Ledges by the Bay

Glen Cove Inn & Suites

Topside Inn

Find out more about Pleasant Point

Frequently asked questions

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