Search Chesapeake City Cottages
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Featured Cottages in Chesapeake City

Chesapeake Romantic Waterfront Home with Private Pool

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Hill Top Cottage with Chickens!

Thunder Hill Retreat - Spacious/Deck/Hot tub

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Quarry Landing - Center of Town & River View - 3 Bedroom

A cottage on the shore of the Delaware River
Chesapeake City 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 Chesapeake City 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 Chesapeake City 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. Chesapeake City 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 Chesapeake City, 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 Chesapeake City cottage accommodation options. It’s about time you got to kick back, and we don’t mean putting your feet up at your desk.
Chesapeake City Cottages essential information
Accommodation | 30 Cottages |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Chesapeake Romantic Waterfront Home with Private Pool, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC, Hill Top Cottage with Chickens!, Thunder Hill Retreat - Spacious/Deck/Hot tub, Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland. , Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay, Private Carriage House Retreat on a 33 Acre Historic Working Estate, Quarry Landing - Center of Town & River View - 3 Bedroom, A cottage on the shore of the Delaware River, Waterfront Cottage on the C&D Canal!, 3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor |
More accommodations in Chesapeake City
Best Cottages in 2025
Top trending hotels in Chesapeake City
