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Pleasant Point Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Pleasant Point vacation rentals

Lobby sitting area

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (493 reviews)
"Its a place to stay."
United States
Todd
$82 nightly
The price is $89
Oct 20 - Oct 21
Total with taxes and fees
Trade Winds on the Bay
Terrace/patio

2. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
$631 nightly
The price is $687
Sep 27 - Sep 28
Total with taxes and fees
Luxury Yurt at Seaside Farm in Friendship
Smart TV

3. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (54 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
$266 nightly
The price is $290
Oct 21 - Oct 22
Total with taxes and fees
2 Bedroom Close to Town Home
1 bedroom, WiFi (free), bed sheets

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (34 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
$150 nightly
The price is $164
Oct 8 - Oct 9
Total with taxes and fees
Simplicity-Just what you need! STR24-20
Property grounds

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (13 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
$241 nightly
The price is $263
Oct 22 - Oct 23
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
Interior

6. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (49 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
$369 nightly
The price is $402
Sep 22 - Sep 23
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Exterior

7. The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
$1,178 nightly
The price is $1,284
Oct 4 - Oct 5
Total with taxes and fees
The Entire Waldoboro Inn
Outdoor dining

8. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.6 out of 10, Excellent, (4 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
$215 nightly
The price is $217
Sep 22 - Sep 23
Total with taxes and fees
Tiny Cottage Near Everything 10
Outdoor dining

9. 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
$164 nightly
The price is $179
Sep 22 - Sep 23
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Smart TV

10. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
$279 nightly
The price is $304
Oct 20 - Oct 21
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
Beach

11. Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (5 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
$658 nightly
The price is $717
Sep 22 - Sep 23
Total with taxes and fees
Pemaquid Escape | Curated Comfort + Hot Tub
Coffee/tea maker, fridge, microwave, stovetop

12. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$233 nightly
The price is $245
Sep 22 - Sep 23
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Coffee/tea maker, fridge, microwave, oven

13. 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, (42 reviews)
"Wonderful place at a great price!"
United States
Stephen H.
$412 nightly
The price is $449
Oct 20 - Oct 21
Total with taxes and fees
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Property grounds

14. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (75 reviews)
"We really enjoyed staying at this house! It was in a good location and was cute and cozy!"
United States
Victoria S.
$546 nightly
The price is $595
Sep 27 - Sep 28
Total with taxes and fees
Oceanview Bungalow Style Home in Owls Head
Terrace/patio

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
8.0 out of 10, Very good, (14 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
$184 nightly
The price is $200
Sep 22 - Sep 23
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Exterior

16. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
$269 nightly
The price is $285
Sep 28 - Sep 29
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
Dining

17. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (11 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
$165 nightly
The price is $180
Sep 22 - Sep 23
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
Interior

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (98 reviews)
"Great location close to town"
United States
Rich W.
$381 nightly
The price is $415
Oct 13 - Oct 14
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
Cottage (2 Bedrooms) | Interior

19. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
$346 nightly
The price is $377
Sep 23 - Sep 24
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
Marina

20. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful house with a beautiful location!"
United States
Angel H.
$434 nightly
The price is $473
Sep 23 - Sep 24
Total with taxes and fees
Harbor/🦞 Pound Access & Views from Large Deck
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

10/10 Excellent
"Great location!! Easy to walk to wherever you want to go"
Kim 1-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 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?

Oceanview Bungalow Style Home in Owls Head: You might want to consider this vacation home rental near Pleasant Point, which is located by the ocean and has a balcony, a terrace, and air-conditioning 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. You can relax into your vacation with a garden and a selection of games.

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 Owls Head Transportation Museum.

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.