Pleasant Point Vacation Rentals

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Our top choices for Pleasant Point vacation rentals

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (394 reviews)
"Clean room and friendly staff "
United States
John
The price is CA $136
CA $148 total
includes taxes & fees
May 31 - Jun 1
Trade Winds on the Bay

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is CA $168
CA $556 total
includes taxes & fees
Jun 1 - Jun 2
Rustic Retreat Across From Lake; Family Friendly!

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is CA $159
CA $360 total
includes taxes & fees
May 28 - May 29
2 Bedroom Close to Town Home

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 stay and host was very responsive with a forgotten item. "
United States
Yvonne T.
The price is CA $175
CA $378 total
includes taxes & fees
May 31 - Jun 1
Peaceful, Centrally Located Home with Seasonal River Views

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (3 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $124
CA $304 total
includes taxes & fees
May 28 - May 29
Cheerful Cottage with Loft 9

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (6 reviews)
"My best friend and I had a great time. Thank you for such a cute cottage so close to the beach. It was very relaxing. "
United States
Jessica F.
The price is CA $190
CA $406 total
includes taxes & fees
May 28 - May 29
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

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, (21 reviews)
"I wish we had more time to spend here! The cabin was well stocked and the location was out of the way, but close enough to sites and eateries "
United States
Sarah D.
The price is CA $288
CA $498 total
includes taxes & fees
Jun 16 - Jun 17
Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (23 reviews)
"We will return next year! Love these little cottages. There is no better location for day tripping. Cottages are well equipped and very comfortable."
United States
Lee R.
The price is CA $149
CA $336 total
includes taxes & fees
May 28 - May 29
Spacious 1 Bedroom Close to Everything 4

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (1 review)
The price is CA $215
CA $397 total
includes taxes & fees
Jun 8 - Jun 9
Romantic Coastal Escape near Harbor

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great central location"
United States
Bruce O.
The price is CA $157
CA $346 total
includes taxes & fees
Jun 8 - Jun 9
Spacious 1 Bedroom Cottage Close to Everything 3

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, (29 reviews)
"Very cute house that was fully equipped for our stay. Great location for touring around Maine to see the sights. Communication was excellent with the host and we would definitely stay here again!"
United States
Elisabeth C.
The price is CA $211
CA $522 total
includes taxes & fees
Jun 3 - Jun 4
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (45 reviews)
"Super clean… great location… fabulous hosts… total pleasure to stay there…"
United States
James B.
The price is CA $300
CA $716 total
includes taxes & fees
May 29 - May 30
In-town, coastal + relaxing in Rockland

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 CA $380
CA $535 total
includes taxes & fees
May 30 - May 31
Dome 1 - Luxury Dome at Come Spring Farm

Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.4 out of 10, Very good, (6 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is CA $214
CA $319 total
includes taxes & fees
Jun 2 - Jun 3
Newly Renovated Cozy Cove Cabin at White Anchor Inn

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
The price is CA $258
CA $458 total
includes taxes & fees
May 28 - May 29
Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (89 reviews)
"Overall a wonderful place for girls weekend. Close proximity to the lighthouses we wanted to see and to Rockland. Clean, beautiful view and easy check in. Host was very responsive with all contacts with questions. "
United States
Anne
The price is CA $311
CA $573 total
includes taxes & fees
May 28 - May 29
Comfortable, Close to Town Home, with Oceanview.

Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
10.0 out of 10, Exceptional, (2 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is CA $90
CA $188 total
includes taxes & fees
Jun 21 - Jun 22
Come Spring Farm Airstream , Lake & farm animals

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is CA $276
CA $392 total
includes taxes & fees
Jun 4 - Jun 5
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (2 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
The price is CA $134
CA $304 total
includes taxes & fees
May 28 - May 29
Tiny Cottage Near Everything 10

ComfyDome Hill-Side Glamping

ComfyDome Hill-Side Glamping
Jefferson
10.0 out of 10, Exceptional, (6 reviews)
"Fun experience!"
United States
Fred R.
The price is CA $224
CA $274 total
includes taxes & fees
Jun 12 - Jun 13
ComfyDome Hill-Side Glamping
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

Find out more about Pleasant Point

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pleasant Point. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: Visitors like this Pleasant Point vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 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 Maine Coastal Islands National Wildlife Refuge.

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.