South Portland Cottages

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Featured Cottages in South Portland

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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.

South Portland Cottage Accommodation

You’re on the go every day, working hard and making that cash. But if you haven’t taken a holiday in months, it’s time to rethink your life choices. It’s time for you to look into South Portland holiday cottages and take a day off—or ten days. Because once you’re all settled in, you won’t want to leave.

Words like charming, adorable, and delightful probably come to mind when you think of country cottages, set in lovely little towns the world over. The same applies to beach cottages—just replace the rolling hills with lapping waves. And while South Portland cottages can’t be in every setting at once, you’ll find that the stunning scenery here is better than all the others combined. Cottages are the perfect retreat from everyday life, with serene surroundings both inside and out and that relaxed vibe that can come only from knowing everything is taken care of. South Portland has an equally charming vibe, and that’s why so many travellers love it.

“Don’t worry, be happy” should be your motto on your next holiday. Well, friend, in South Portland, that’s not just the motto of visitors; the locals are living that theme every day. So take a break from that presentation you’re working on and make a different graph instead—of Wotif’s low prices on over South Portland cottage accommodation options. It’s about time you got to kick back, and we don’t mean putting your feet up at your desk.

South Portland Cottages essential information

Accommodation
305 Cottages
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Popular accommodation
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access, Charming cottage w/ loft on 3 acres of secluded marsh and 7 minute walk to beach, WATERFRONT ON PETTENGILL POND, Summer 2025! Goose Rocks Beach, Kennebunkport, Private Contemporary Artist's Tree House on two acres with perennial gardens. , The Great Escape - Picturesque Sebago Lake, Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout, Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island., The Outlet House, Comfortable Cottage, Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!, Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5, 2 bedroom cottage

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