Book Holiday Homes in Chester
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Chester

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Historic Row Home 1 Block from Gate 1 at USNA!

Charming Historic Annapolis Home With Two Off-street Parking Places!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Million Dollar View of the Chesapeake Bay

Large 2 bedroom house with private parking in a nice neighborhood

Walk to Everything House
Chester Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.
Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chester Holiday Homes essential information
Accommodation | 697 Holiday Homes |
|---|---|
Lowest Price | AU$146 |
Highest Price | AU$1,119 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Historic Row Home 1 Block from Gate 1 at USNA!, Charming Historic Annapolis Home With Two Off-street Parking Places!, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !, Million Dollar View of the Chesapeake Bay, Large 2 bedroom house with private parking in a nice neighborhood, Walk to Everything House |
Top trending hotels in Chester

Historic Inns of Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Sonesta ES Suites Annapolis

DoubleTree by Hilton Hotel Annapolis
More ways to explore Chester
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
