South Portland Cottages

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Cottages in South Portland

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

Old Orchard Beach ME

$330 nightly

$360 total

Sep 22 - Sep 23

Total with taxes and fees

With a stay at this cottage in Old Orchard Beach, you'll be within a 5-minute drive of Old Orchard Beach and Old Orchard Beach Pier.

Kitchen

Washer

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

Gray ME

Located in Gray, this cottage is on the waterfront, a 1-minute drive from Little Sebago Lake and 9 minutes from Maine Wildlife Park.

Kitchen

Free WiFi

Delightful 3-bedroom cottage in charming Biddeford Pool/Fortunes Rocks Maine.

Biddeford ME

When you stay at this cottage in Biddeford, you'll be on the waterfront, within a 5-minute drive of Fortunes Rock Beach and Saint Brendan's Chapel.

Kitchen

Pet friendly

Kinney Shores Beach Cottage•AC•New•Renovated•Steps to 7 Mile Sandy Beach•Parking

Saco ME

With a stay at this cottage in Saco (Kinney Shores), you'll be within a 5-minute drive of Old Orchard Beach and Old Orchard Beach Pier.

Kitchen

Washer

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Old Orchard Beach ME

With a stay at this cottage in Old Orchard Beach, you'll be on the beach, steps from Old Orchard Beach and a 2-minute drive from Old Orchard Beach Pier.

Hot Tub

Kitchen

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

WINDHAM ME

Located in Windham, this cottage is on the waterfront, within a 15-minute drive of Mercy Primary Care and Forest Lake.

Kitchen

Pet friendly

Cottage by the Sea #3 by Bayley Vacation Rentals

Old Orchard Beach ME

Located in Old Orchard Beach (Surfside), this cottage is steps from Old Orchard Beach and a 2-minute drive from Old Orchard Beach Pier.

Kitchen

Washer

Cozy Cottage with stunning views of Stover's Cove.

Harpswell ME

With a stay at this cottage in Harpswell, you'll be steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.

Washer

Dryer

2-bedroom cottage steps from the beach in Old Orchard Beach with AC & an office

Old Orchard Beach ME

With a stay at this cottage in Old Orchard Beach, you'll be steps from Old Orchard Beach and a 2-minute drive from Old Orchard Beach Pier.

Kitchen

Free WiFi

Fall 2026! Charming Cottage—Goose Rocks Beach, Kennebunkport

Kennebunkport ME

With a stay at this cottage in Kennebunkport (Goose Rocks Beach), you'll be within a 15-minute drive of Dock Square and Goose Rocks Beach.

Kitchen

Washer

THIS IS THE PLACE - Intimate cottage with oceanfront views and AC!

Harpswell ME

When you stay at this cottage in Bailey Island, you'll be on the beach, within a 5-minute walk of Casco Bay and Mackerel Cove.

Kitchen

Pet friendly

Quiet Cottage surrounded by beaches, restaurants, hiking, shops & Kennebunkport

Arundel ME

With a stay at this cottage, you'll be centrally located in Kennebunkport, within a 10-minute drive of Dock Square and Arundel Barn Playhouse.

Kitchen

Washer

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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.