Search South Portland Cottage Rentals from CA $241

    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
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select South Portland Cottages

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Exterior

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (39)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Property grounds

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.6 out of 10, Exceptional, (49)
"We had a wonderful time at this house! It’s perfectly situated by the beach, just a stone’s throw away from the charming village of Biddeford Pool. You can even grab some fresh, steamed lobster at the grocery store there. The house offers breathtaking views of the sunset and the bay, and there’s plenty of great outdoor space for relaxation. Parking is also a breeze. The host is incredibly friendly and responsive, making our stay even more enjoyable. We even had a travel massage for our...
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Exterior

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.6 out of 10, Exceptional, (4)
"This was a gem, and the location was perfect for what we need. Very charming and such a comfortable bed"
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
WATERFRONT ON PETTENGILL POND
Exterior

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Little Miss Cottages
Exterior

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
The Great Escape - Picturesque Sebago Lake
Terrace/patio

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (50)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (33)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is CA $241
CA $425 total
includes taxes & fees
Sep 1 - Sep 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
Charming cottage w/ loft on 3 acres of secluded marsh and 7 minute walk to beach
Property grounds

Charming cottage w/ loft on 3 acres of secluded marsh and 7 minute walk to beach

9.0 out of 10, Wonderful, (2)
"The house is in a great location and was perfect for our family of three, though there were two extra twin beds in the loft that we didn’t even use so a larger family may enjoy it as well. The view from the back porch is beautiful, especially at sunrise and sunset. The walk to the beach is very easy if you don’t have a lot to haul, and the two beach chairs they have at the house are nice and light. Highly recommend checking out Cape Pier Chowder House and Ultramar which are only a few minutes...
Charming cottage w/ loft on 3 acres of secluded marsh and 7 minute walk to beach
Summer 2025! Goose Rocks Beach, Kennebunkport
Exterior

Summer 2025! Goose Rocks Beach, Kennebunkport

9.8 out of 10, Exceptional, (18)
"My family and I thoroughly enjoyed our time here!"
Summer 2025! Goose Rocks Beach, Kennebunkport
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Exterior

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (45)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Quaint Cottage Just Steps From The Beach And The Saco River
Exterior

Quaint Cottage Just Steps From The Beach And The Saco River

9.8 out of 10, Exceptional, (16)
"We had a very nice, clean and comfortable stay!"
Quaint Cottage Just Steps From The Beach And The Saco River
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
Property grounds

Waterfront Lake Arrowhead Home w/ Kayaks & Grill!

9.4 out of 10, Exceptional, (22)
"We enjoyed our stay. It was comfy cozy."
Waterfront Lake Arrowhead Home w/ Kayaks & Grill!
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Outdoor dining

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

10.0 out of 10, Exceptional, (12)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Property grounds

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
A Quiet Cottage close to beaches, Kennebunkport and Kennebunk. Polly’s Place.
Exterior

A Quiet Cottage close to beaches, Kennebunkport and Kennebunk. Polly’s Place.

10.0 out of 10, Exceptional, (30)
"The house was much nicer than we expected. We will be back!!"
A Quiet Cottage close to beaches, Kennebunkport and Kennebunk. Polly’s Place.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Portland Hotel Reviews

Quality Inn & Suites

Quality Inn & Suites

10/10 Excellent
"The hotel was clean, quiet and felt comfortable. The rooms are equipped with clothes iron, hair dryer and coffee pot. They provide cllean towels and toiletries. "
Melissa 1-night trip
Posted 21 hours ago
Quality Inn & Suites