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12 Sep - 14 Sep
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Cottages in South Portland

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, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Cozy coastal 2-bedroom cottage, short walk to Goose Rocks Beach.
Property grounds

Cozy coastal 2-bedroom cottage, short walk to Goose Rocks Beach.

10.0 out of 10, Exceptional, (3)
"Beautiful cottage, great pools and a walk to the beach. We really enjoyed our stay. "
Cozy coastal 2-bedroom cottage, short walk to Goose Rocks Beach.
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

9.8 out of 10, Exceptional, (7)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Exterior

Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~

10.0 out of 10, Exceptional, (4)
"Amazing location and trip! Great communication with owner Michelle. Will come again "
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
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, (88)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
The Great Escape - Picturesque Sebago Lake
Terrace/patio

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (53)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Lakefront Cottage - private dock, large decks, large fire pit
Outdoor dining

Lakefront Cottage - private dock, large decks, large fire pit

9.4 out of 10, Exceptional, (24)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Exterior

Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path

9.0 out of 10, Wonderful, (76)
"Loved how close it was to the beach.. very sweet little cottage."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
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, (45)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
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

10.0 out of 10, Exceptional, (1)
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, (31)
"The house was much nicer than we expected. We will be back!!"
A Quiet Cottage close to beaches, Kennebunkport and Kennebunk. Polly’s Place.
Fall Getaway 2025! Sunny, Cozy, & Clean - Goose Rocks Beach, Kennebunkport
Exterior

Fall Getaway 2025! Sunny, Cozy, & Clean - Goose Rocks Beach, Kennebunkport

10.0 out of 10, Exceptional, (21)
"My family and I thoroughly enjoyed our time here!"
Fall Getaway 2025! Sunny, Cozy, & Clean - Goose Rocks Beach, Kennebunkport
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Exterior

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

10.0 out of 10, Exceptional, (53)
"Beautiful views from a charming cottage with kind neighbors. Eclectic styled home which we enjoyed. Would stay again!!"
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Cozy Cottage with stunning views of Stover's Cove.
Exterior

Cozy Cottage with stunning views of Stover's Cove.

9.8 out of 10, Exceptional, (8)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.
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, (35)
"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 AED 459
AED 917 total
includes taxes & fees
8 Sep - 9 Sep
Large 2BD cottage 10 min to Pier & Beach Pets ok
Cute cottage only a 10 min walk to the beach.
Exterior

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (12)
"Our stay was perfect. The house is really cute and well located for going to the beach."
Cute cottage only a 10 min walk to the beach.
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

9.4 out of 10, Exceptional, (86)
"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
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Property grounds

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

9.8 out of 10, Exceptional, (52)
"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
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Terrace/patio

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

9.8 out of 10, Exceptional, (33)
"Have stayed here two times over the years and it’s a great place for small families. We thoroughly enjoyed our recent visit."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
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 South Portland Hotel Reviews

Frequently asked questions

How much do cottages in South Portland cost?
Rates for cottages in South Portland range between and per night. Whatever your budget, you're sure to find the ideal place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in South Portland with Expedia?
We think that a vacay should be hassle-free, so if you're searching for cottages in South Portland at an affordable price, Expedia can help. Stick to the budget and check in to a low-cost option far away from the hustle and bustle, or book a 5-star cottage to really spoil your favorite people.
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