Chesapeake Bay 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
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Cottages in Chesapeake Bay

Key West Cottages

NEW PET FRIENDLY LISTING ALERT!!

Lovely backyard cottage with easy access to metro, shops, dining!

Family and Pet-Friendly, Waterfront with Pier

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Cozy Little Cottage on chincoteague island va.

Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Chesapeake Bay 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 Bay 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 Bay 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 Bay 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 Bay, 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 Bay 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 Bay Cottages essential information
Accommodation | 80 Cottages |
---|---|
Lowest Price | NZ$185 |
Highest Price | NZ$324 |
Popular accommodation | Key West Cottages, NEW PET FRIENDLY LISTING ALERT!!, Lovely backyard cottage with easy access to metro, shops, dining!, Family and Pet-Friendly, Waterfront with Pier, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6, 1BR Waterfront cottage with a view of the wild Chincoteague ponies!, 2BR Waterfront Cottage with the Most Spectacular View of lighthouse!, Cozy Little Cottage on chincoteague island va., Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies! , Cozy Mother-in-Law Suite |
Top trending hotels in Chesapeake Bay

Washington Plaza Hotel
Top cities with Cottages
More Cottages
More accommodations in Chesapeake Bay
More destinations for you
- Hotels in Chicago
- Hotels in Groveland
- Hotels in San Francisco
- Hotels in Pullman
- Hotels in Maui
- Hotels in Anaheim
- Hotels in Florida Keys
- Hotels in Boston
- Hotels in Venice
- Florida Keys All Inclusive Hotels
- Hotels in Oahu
- Hotels in Pocono Mountains
- Hotels in Royal Oak
- Hotels in Washington
- Hotels in New York
- Hotels in Nashville
- Hotels in Christmas
- Hotels in Honolulu
- Hotels in Orlando
- Hotels in Las Vegas
- New York Apartment Hotels
- Hotels in San Diego
- Hotels in Los Angeles
- Hotels in Houston
^Eligibility requirements and conditions apply