Search Cottages in Pleasant Point

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 26 Cottages in Pleasant Point with updated reviews, rates, and availability.

Historic Waldoboro House Near Lakes, Boating, Etc!
Interior

Historic Waldoboro House Near Lakes, Boating, Etc!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
Historic Waldoboro House Near Lakes, Boating, Etc!
'sprucewold' Boothbay Harbor Cottage w/ Deck
Exterior

'sprucewold' Boothbay Harbor Cottage w/ Deck

3.0 star property
'sprucewold' Boothbay Harbor Cottage w/ Deck
Charming East Boothbay Cottage w/ Large Yard!
TV, books

Charming East Boothbay Cottage w/ Large Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Really nice place to stay to visit Boothbay Region"
Charming East Boothbay Cottage w/ Large Yard!
3 Mi to Boothbay Harbor: Coastal Colorful Home!
Interior

3 Mi to Boothbay Harbor: Coastal Colorful Home!

3.0 star property
3 Mi to Boothbay Harbor: Coastal Colorful Home!
Deck w/ Water Views: Quiet East Boothbay Retreat!
Interior

Deck w/ Water Views: Quiet East Boothbay Retreat!

3.0 star property
Deck w/ Water Views: Quiet East Boothbay Retreat!
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

3.0 star property
Updated Tiny House: Walk to Wiscasset Village
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
Exterior

Boothbay Harbor Cabin w/ Spacious Deck & Yard!

3.0 star property
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
Rustic Retreat Across From Lake; Family Friendly!
Cottage (2 Bedrooms) | Interior

Rustic Retreat Across From Lake; Family Friendly!

3.0 star property
8.0 out of 10, Very Good, (1)
"I liked that it was by the lake quiet and secluded. "
Rustic Retreat Across From Lake; Family Friendly!
Pauls Cottage in Tenants Harbor, 1 Min to Shore
Terrace/patio

Pauls Cottage in Tenants Harbor, 1 Min to Shore

3.0 star property
Pauls Cottage in Tenants Harbor, 1 Min to Shore
Charming Owls Head Retreat: 2 Mi to Rockland Coast
Exterior

Charming Owls Head Retreat: 2 Mi to Rockland Coast

3.0 star property
Charming Owls Head Retreat: 2 Mi to Rockland Coast
On-site Pond: Spacious Family Home in Jefferson!
Interior

On-site Pond: Spacious Family Home in Jefferson!

3.0 star property
On-site Pond: Spacious Family Home in Jefferson!
Historic Friendship Boat House Near Back River!
Interior

Historic Friendship Boat House Near Back River!

3.0 star property
Historic Friendship Boat House Near Back River!
Quiet & Lovely Lakefront Cottage for Families!
Microwave, oven, stovetop, cookware/dishes/utensils

Quiet & Lovely Lakefront Cottage for Families!

3.0 star property
Quiet & Lovely Lakefront Cottage for Families!
Owls Head Getaway: Private Decks w/ Ocean View!
Interior

Owls Head Getaway: Private Decks w/ Ocean View!

3.0 star property
Owls Head Getaway: Private Decks w/ Ocean View!
Rockland Home w/ Deck 5 Mins to Historic Downtown!
Terrace/patio

Rockland Home w/ Deck 5 Mins to Historic Downtown!

3.0 star property
Rockland Home w/ Deck 5 Mins to Historic Downtown!
Lovely Waterfront Owls Head Home w/ Own Beach
House (3 Bedrooms) | Interior

Lovely Waterfront Owls Head Home w/ Own Beach

3.0 star property
Lovely Waterfront Owls Head Home w/ Own Beach
Charming Cottage w/ Patio, Walk to Boothbay Harbor
Terrace/patio

Charming Cottage w/ Patio, Walk to Boothbay Harbor

3.0 star property
Charming Cottage w/ Patio, Walk to Boothbay Harbor
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
2 bedrooms, laptop workspace, iron/ironing board, bed sheets

Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

3.0 star property
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
4 Mi to Boothbay Harbor: Quiet Retreat w/ Deck
Interior

4 Mi to Boothbay Harbor: Quiet Retreat w/ Deck

3.0 star property
4 Mi to Boothbay Harbor: Quiet Retreat w/ Deck
Boothbay Harbor Beach House By Park & Restaurants!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Boothbay Harbor Beach House By Park & Restaurants!

3.0 star property
Boothbay Harbor Beach House By Park & Restaurants!
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.
Don't see what you're looking for?
See all available properties in Pleasant Point
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pleasant Point

Trade Winds on the Bay
Premier Double Room, 2 Double Beds, Balcony, Harbor View | Free WiFi, bed sheets

Trade Winds on the Bay

4.0 star property
8.2 out of 10, Very Good, (207)
"I liked that it was centrally located."
The price is NT$3,937
NT$4,291 total
includes taxes & fees
Apr 27 - Apr 28
Trade Winds on the Bay
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.