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Top Holiday Rentals in Pleasant Point

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (246)
"Location is amazing."
The price is £165
includes taxes & fees
18 Aug - 19 Aug
Trade Winds on the Bay

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

2.0 star property
9.4 out of 10, Exceptional, (9)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

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

The price is £152
includes taxes & fees
17 Aug - 18 Aug
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

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

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (75)
"Fantastic location, owners were nearby and easy to communicate with for any questions. Perfect views and cozy apartment for our family of 3. Would definitely stay here again!"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Newly Renovated Cozy Cove Cabin at White Anchor Inn

The price is £176
includes taxes & fees
31 Aug - 1 Sept
Newly Renovated Cozy Cove Cabin at White Anchor Inn

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

10.0 out of 10, Exceptional, (100)
"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

Dog-friendly bay view home - water views, dock access

6.6 out of 10, (7)
"Nice and quiet. Beautiful view of the water"
Dog-friendly bay view home - water views, dock access

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

10.0 out of 10, Exceptional, (127)
"This was by far one of the best places we have ever stayed , it was so well decorated and stocked with anything you would need. Spotlessly clean and really felt like home. If I ever get back to Maine it will be my go to place to stay"
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (74)
"Clean"
The price is £308
includes taxes & fees
1 Sept - 2 Sept
Comfortable, Close to Town Home, with Oceanview.

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

10.0 out of 10, Exceptional, (119)
"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

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

10.0 out of 10, Exceptional, (92)
"Beautiful home and scenery, hosts were communicative. "
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.6 out of 10, Exceptional, (30)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

Elegant riverside retreat with breathtaking views and modern comforts

Elegant riverside retreat with breathtaking views and modern comforts

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

9.8 out of 10, Exceptional, (119)
"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

Camp #2 - A "Pleasure" with 1G Wifi

9.6 out of 10, Exceptional, (12)
"Beautiful property, friendly owners, really cute camp sites and trailers, all in terrific shape. It blended the outdoors more into our trip, we played corn hole, had a couple bonfires, thoroughly enjoyed ourselves."
Camp #2 - A "Pleasure" with 1G Wifi

Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

10.0 out of 10, Exceptional, (2)
"We loved how spacious and accommodating this home was, as well as it's great proximity to downtown Boothbay Harbor."
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort

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 £566
includes taxes & fees
30 Aug - 31 Aug
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

2.0 star property
9.0 out of 10, Wonderful, (102)
"The place was very clean. Right on the water. Spectacular views. Sunrise in the morning. A great experience. A lovely get away. Want to go back again"
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"My husband and our 1 year old daughter had a wonderful stay. The home is close to everything and has everything you may need. Would love to stay again. "
A Charming Waterfront Cottage with Touches of Elegance
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

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?

Comfortable, Close to Town Home, with Oceanview.: This holiday home rental outside of Pleasant Point offers a patio, a private garden and a BBQ 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 that you can cook with friends or family.

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 Maine Coastal Islands National Wildlife Refuge. In the wider area, you’ll find Marshall Point Lighthouse and St. George River.

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.