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Pleasant Point Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Pleasant Point vacation rentals

House, 1 Queen Bed (Beehive Cottage) | Living area

1. Bee Hive Cottage, Romantic Maine Waterfront Cottag

Bee Hive Cottage, Romantic Maine Waterfront Cottag
2.0 star property
Cushing
$812 nightly
The price is $884
Aug 8 - Aug 9
Total with taxes and fees
Bee Hive Cottage, Romantic Maine Waterfront Cottag
Interior

2. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.0 out of 10, Very Good, (4 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
$303 nightly
The price is $330
Aug 19 - Aug 20
Total with taxes and fees
Come Spring Farm Airstream , Lake & farm animals
1 bedroom, WiFi

3. ComfyDome Pond-Side Glamping

ComfyDome Pond-Side Glamping
Jefferson
10.0 out of 10, Exceptional, (6 reviews)
"A lovely stay - Seth was very kind and attentive, and our starry night sky was beyond compare. We will come again! "
United States
Fiona S.
$186 nightly
The price is $203
Aug 21 - Aug 22
Total with taxes and fees
ComfyDome Pond-Side Glamping
Outdoor dining

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

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
$167 nightly
The price is $182
Aug 30 - Aug 31
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
1 bedroom, WiFi (free), bed sheets

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

Simplicity-Just what you need! STR24-20
Rockland
9.6 out of 10, Exceptional, (28 reviews)
"Very clean and allows for easy access around the area! "
United States
Sarah V.
$152 nightly
The price is $166
Sep 6 - Sep 7
Total with taxes and fees
Simplicity-Just what you need! STR24-20
Terrace/patio

6. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
$666 nightly
The price is $726
Sep 6 - Sep 7
Total with taxes and fees
Luxury Yurt at Seaside Farm in Friendship
Lobby sitting area

7. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (444 reviews)
"Great stay, great location."
United States
Jerold
$210 nightly
The price is $229
Aug 9 - Aug 10
Total with taxes and fees
Trade Winds on the Bay
Beach nearby

8. Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
$354 nightly
The price is $386
Sep 1 - Sep 2
Total with taxes and fees
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Property grounds

9. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.8 out of 10, Exceptional, (7 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.
$252 nightly
The price is $275
Sep 1 - Sep 2
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
House (3 Bedrooms) | Front of property

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

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
$450 nightly
The price is $491
Aug 9 - Aug 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Smart TV

11. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (35 reviews)
"Great Stay!"
United States
Pastor Heidi G.
$317 nightly
The price is $346
Sep 1 - Sep 2
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Terrace/patio

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
$183 nightly
The price is $199
Aug 10 - Aug 11
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Smart TV

13. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (51 reviews)
"We enjoyed staying at this site but we had difficulty with the address. I would recommend putting the number 67 on the outside of the mud room door, which would make it much easier to find the location A member of our party had difficulty sleeping on the pull out couch and recommended a thicker mattress. We also smelled cigarettes upon entry into the building but once the door was open for a short time the smell went away. I would definitely stay at this site again when I the area."
United States
April
$303 nightly
The price is $330
Sep 1 - Sep 2
Total with taxes and fees
2 Bedroom Close to Town Home
Coffee/tea maker, fridge, microwave, stovetop

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

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"We had a lovely time in Maine and enjoyed the farm house for our downtime and sleeping. It was exactly what we were looking for and would 100% stay here again and recommend it to others. Thank you!"
United States
Carrie Plympton F.
$458 nightly
The price is $499
Aug 9 - Aug 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Coffee/tea maker, fridge, microwave, stovetop

15. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$261 nightly
The price is $276
Sep 1 - Sep 2
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Outdoor dining

16. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.0 out of 10, Very Good, (3 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
$256 nightly
The price is $259
Sep 1 - Sep 2
Total with taxes and fees
Tiny Cottage Near Everything 10
Coffee/tea maker, fridge, microwave, oven

17. 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, (38 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
$446 nightly
The price is $486
Aug 31 - Sep 1
Total with taxes and fees
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Property grounds

18. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (67 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.
$520 nightly
The price is $567
Aug 19 - Aug 20
Total with taxes and fees
Oceanview Bungalow Style Home in Owls Head
Living area

19. Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Pemaquid Beach
9.2 out of 10, Wonderful, (5 reviews)
"Loved our stay"
United States
Jeanne
$354 nightly
The price is $386
Sep 1 - Sep 2
Total with taxes and fees
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Interior

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (95 reviews)
"Great location close to town"
United States
Rich W.
$412 nightly
The price is $449
Aug 18 - Aug 19
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
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

Tugboat Inn

Tugboat Inn

8/10 Good
"/"
Michael 4-night trip
Posted 1 hour ago
Tugboat Inn

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 $199 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.

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?

Comfortable, Close to Town Home, with Oceanview.: You might want to consider this vacation rental near Pleasant Point, which offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable 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.

How many vacation rentals will I find in Pleasant Point?

Choose from 9 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.