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Featured Cottages in Chestertown

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Chesapeake Cottages- 2 Quaint Waterfront Retreats

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Secluded Cozy Cottage in Historic Downtown

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Cozy, unique, historic registered cottage on the Corsica River!

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Chestertown 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 Chestertown 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 Chestertown 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. Chestertown 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 Chestertown, 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 Chestertown cottage accommodation options. It’s about time you got to kick back, and we don’t mean putting your feet up at your desk.
Chestertown Cottages essential information
Accommodation | 62 Cottages |
|---|---|
Lowest Price | AU$111 |
Highest Price | AU$1,333 |
Popular accommodation | Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly, Chesapeake Cottages- 2 Quaint Waterfront Retreats, 5 Mi to Downtown Baltimore: Quiet Home w/ Porch, Secluded Cozy Cottage in Historic Downtown, Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi, Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Cozy, unique, historic registered cottage on the Corsica River!, Rare find! Chic cottage, salt water heated pool May 15-Oct15. , Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Eastern shore beachfront cottage with stunning sunset views!, Eastern Shore beach cottage get-away |
Top trending hotels in Chestertown

Comfort Inn & Suites Chestertown
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