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Pleasant Point Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Pleasant Point holiday rentals

Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (417 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
The price is HK$1,391
HK$1,516 total
includes taxes & fees
28 Jun - 29 Jun
Trade Winds on the Bay
Terrace/patio

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.6 out of 10, Good, (9 reviews)
"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "
United States
Nichole W.
The price is HK$1,023
HK$1,568 total
includes taxes & fees
25 Jun - 26 Jun
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Interior

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 HK$957
HK$3,160 total
includes taxes & fees
26 Jun - 27 Jun
Rustic Retreat Across From Lake; Family Friendly!
Property grounds

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.6 out of 10, Exceptional, (4 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.
The price is HK$1,137
HK$2,153 total
includes taxes & fees
29 Jun - 30 Jun
Bright 2-Bedroom Apartment Near Downtown Thomaston
Beach nearby

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 HK$1,121
HK$2,179 total
includes taxes & fees
25 Jun - 26 Jun
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
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 HK$2,540
HK$4,341 total
includes taxes & fees
22 Jul - 23 Jul
Oceanfront Maine Cottage, Private Shoreline, Sunset Views, Near Lighthouse.
Fridge, microwave, stovetop, coffee/tea maker

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
The price is HK$1,035
HK$2,155 total
includes taxes & fees
25 Jun - 26 Jun
Spacious 1 Bedroom Cottage Close to Everything 5
TV, offices

Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is HK$1,098
HK$4,547 total
includes taxes & fees
25 Jun - 26 Jun
Fully Updated Airy Historic Home in West Rockport
Beach nearby

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)
"Great beach cottage !"
United States
Gwen M.
The price is HK$1,164
HK$2,423 total
includes taxes & fees
1 Jul - 2 Jul
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
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 HK$2,078
HK$4,051 total
includes taxes & fees
22 Jul - 23 Jul
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
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 HK$1,372
HK$2,640 total
includes taxes & fees
29 Jun - 30 Jun
Peaceful, Centrally Located Home with Seasonal River Views
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 HK$953
HK$1,406 total
includes taxes & fees
25 Jun - 26 Jun
Simplicity-Just what you need! STR24-20
Exterior

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views

Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Camden
The price is HK$1,588
HK$2,645 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Waterfront Guesthouse Getaway in Camden with Mountain Views
Outdoor dining

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 HK$957
HK$1,966 total
includes taxes & fees
6 Jul - 7 Jul
Tiny Cottage Near Everything 10
Living area

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 HK$1,121
HK$2,179 total
includes taxes & fees
25 Jun - 26 Jun
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
2 bedrooms, iron/ironing board, bed sheets

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 HK$902
HK$1,984 total
includes taxes & fees
29 Jun - 30 Jun
Cheerful Cottage with Loft 9
Exterior

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 HK$1,027
HK$2,146 total
includes taxes & fees
29 Jun - 30 Jun
Spacious 1 Bedroom Cottage Close to Everything 3
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 HK$1,294
HK$1,980 total
includes taxes & fees
25 Jun - 26 Jun
Dome 1 - Luxury Dome at Come Spring Farm
Interior

Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
The price is HK$1,380
HK$4,409 total
includes taxes & fees
7 Jul - 8 Jul
Quiet & Lovely Lakefront Cottage for Families!
Interior

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (43 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is HK$1,757
HK$3,171 total
includes taxes & fees
1 Jul - 2 Jul
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
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

Harborline Hotel

Harborline Hotel

8/10 Good
"Nice location"
Leigh 1-night trip
Posted 1 hour ago
Harborline Hotel

Find out more about Pleasant Point

Search for holiday rentals in Pleasant Point on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasant Point using one of the methods below:

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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 9 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 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.