Holiday Rentals in Pleasant Point

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Holiday Rentals in Pleasant Point

Trade Winds on the Bay
Water view

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (259)
"Great view "
Trade Winds on the Bay
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Fridge, microwave, oven, stovetop

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
8.8 out of 10, Excellent, (11)
"Very peaceful !"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Property grounds

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (103)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (145)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Outdoor dining

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (38)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Morning sun, coffee in hand, a good book and so much more...
Property grounds

Morning sun, coffee in hand, a good book and so much more...

9.8 out of 10, Exceptional, (82)
"Really enjoyed being on the lake and so close to town."
Morning sun, coffee in hand, a good book and so much more...
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Outdoor dining

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

9.4 out of 10, Exceptional, (25)
"Perfect base for exploring the mid-coast region. "
The price is €494
includes taxes & fees
12 Sept - 13 Sept
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Make Shimmering River Retreat your Maine Coastal getaway!
Fridge, microwave, oven, stovetop

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (37)
"It was a very nice place for a family vacation. There was plenty of room for all of us (10).Yard and inside games provided along with kayaks for the river and a pool."
Make Shimmering River Retreat your Maine Coastal getaway!
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Terrace/patio

Newly Renovated Cozy Cove Cabin at White Anchor Inn

8.0 out of 10, Very good, (3)
"As advertised, comfy bed cozy cabin. Would stay again "
The price is €156
includes taxes & fees
21 Sept - 22 Sept
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Comfortable, Close to Town Home, with Oceanview.
Interior

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (76)
"We had a great stay while in town for a family event. We were ecstatic to be able to take our family dog with us on the trip. The view from the back deck was incredible and close to many local parks for hiking."
The price is €334
includes taxes & fees
12 Sept - 13 Sept
Comfortable, Close to Town Home, with Oceanview.
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Exterior detail

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (87)
"My husband and I just retired and enjoyed this place immensely! Especially the fireplace and the quiet space."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Property grounds

Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

10.0 out of 10, Exceptional, (132)
"Property was perfect for a stay of two. Morning coffee was enjoyed with a beautiful view of the water and comfy patio chairs. Second story bedroom loft had a wall of windows to showcase the ocean view. It was noted that the property owners put thought into every amenity. "
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.
Renovated home with water views, dock access, - dogs okay
Fridge, microwave, oven, stovetop

Renovated home with water views, dock access, - dogs okay

6.6 out of 10, (8)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, - dogs okay
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Interior

Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

10.0 out of 10, Exceptional, (94)
"Beautiful home and scenery, hosts were communicative. "
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Terrace/patio

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

6.0 out of 10, (2)
"Nice place to stay for a quick trip to the area! Would stay there again. "
The price is €134
includes taxes & fees
29 Sept - 30 Sept
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
On the beach, sun-loungers

Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views

10.0 out of 10, Exceptional, (123)
"We had a lovely time staying at your wonderfully cozy and charming property - thank you for a great experience!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Interior

Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway

9.8 out of 10, Exceptional, (66)
"Beautiful and very cozy stay close to everything you’d want to do, hike, explore, enjoy. Whirlpool jets in the tub was great after a long hike and we loved stargazing on the terrace. "
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
On the beach, sun-loungers

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

10.0 out of 10, Exceptional, (123)
"This property was more than we could have asked for. The view was spectacular the hosts were great and we had more amenities than we could have asked for."
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Fridge, microwave, oven, stovetop

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (92)
"We enjoyed the view from this home and the location very much. Easy walkability to town and having Dunston’s right down the street was a fun perk. The communal spaces are small but cozy. The weather was rainy while we were there so we spent a lot of time nestled up reading and enjoying the view. My only complaint was there was no coffee provided—pretty small gripe and easily remedied!"
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
Property grounds

Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock

10.0 out of 10, Exceptional, (78)
"Another great stay"
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock
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

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, apart-hotels, 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 €134 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.

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.