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In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
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Cottages in South Portland

Our top choices for South Portland cottages

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, (48)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
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, (7)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Exterior

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (60)
"My stay at the cottage was exactly what I needed, it’s an updated beachy vibe and excellent use of every space including some rainy day puzzles and books! The small fenced in yard was perfect for the furry family members, and you cant beat the location, such a close walk to the beach, and just far enough away from the busy OOB hustle! Would definitely stay again! "
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
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
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Lakefront Cottage - private dock, large decks, large fire pit
Outdoor dining

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

9.2 out of 10, Wonderful, (25)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
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, (23)
"My family and I thoroughly enjoyed our time here!"
Fall Getaway 2025! Sunny, Cozy, & Clean - Goose Rocks Beach, Kennebunkport
Lakefront Traditional 4-bedroom cottage in Frye Island
Exterior

Lakefront Traditional 4-bedroom cottage in Frye Island

2.0 star property
10.0 out of 10, Exceptional, (3)
"Our family of four (with older kids) had a peaceful and memorable stay at this cozy lakefront cottage. The setting is stunning—perfect for disconnecting and enjoying nature. The cottage is right on the water with a dock (no beach, but several are nearby), and we loved kayaking and watching sunsets from the deck.Some rooms are a bit tight, and Frye Island’s ferry access and dirt roads can be inconvenient—but if you’re looking for quiet, beauty, and simplicity, it’s worth it. The owner was...
Lakefront Traditional 4-bedroom cottage in Frye Island
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, (36)
"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"
Large 2BD cottage 10 min to Pier & Beach Pets ok
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

9.4 out of 10, Exceptional, (9)
"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
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, (88)
"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
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)
"Clean, cute cottage for four on a steep waterfront lot with a beautiful vista. Nice kitchen for exended stay. Great fireplace."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
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, (5)
Coastal Charm 2 Bedroom Beach Cottage ~Just Steps to the Beach in Kinney Shores~
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Terrace/patio

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.8 out of 10, Excellent, (21)
"Very beautiful and easy to communicate with the property management "
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Luxurious Beachfront New England Cottage
Property grounds

Luxurious Beachfront New England Cottage

10.0 out of 10, Exceptional, (6)
"This house was gorgeous and we highly enjoyed our stay. We will be back!!"
Luxurious Beachfront New England Cottage
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Exterior

Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool

10.0 out of 10, Exceptional, (4)
"It was a great stay. The house is in wonderful condition. The hosts were very helpful and our stay was relaxing and enjoyable. "
The price is SAR 1,482
SAR 2,547 total
includes taxes & fees
23 Oct - 24 Oct
Brand new charming cottage next to the pristine sandy beaches of Biddeford Pool
Oceanfront Escape: Deck & Granite Steps to Shore
Property grounds

Oceanfront Escape: Deck & Granite Steps to Shore

9.4 out of 10, Exceptional, (3)
"Everything was beautiful and we loved our stay!"
Oceanfront Escape: Deck & Granite Steps to Shore
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.
Updated Long Island Maine Cottage
Exterior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
2 bedroom cottage
Smart TV

2 bedroom cottage

8.8 out of 10, Excellent, (8)
"quiet, clean, short walk to beach"
2 bedroom cottage
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"the property is very nice, the garden wonderful, the staff very friendly and helpful, the morning coffee area excellent, the rooms very comfortable."
Kerri 2-night trip
Posted 2 days ago
Portland Harbor Hotel

Frequently asked questions

How much do cottages in South Portland cost?
Rates for cottages in South Portland range between SAR 2,547 and SAR 2,547 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.
How can I find cheap cottages in South Portland?
The best way to get cheap cottages in South Portland is with Expedia's useful filter tool. Narrow your search by amenities, star rating and budget to grab excellent rates with only a few clicks.