Kent Island Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Kent Island

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

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.

Kitchen

Washer

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton MD

A stay at this vacation home places you in the heart of Crofton, within a 5-minute drive of Walden Golf Club and Regal Waugh Chapel.

Kitchen

Washer

Private Pool & Stunning Bay Views on Kent Island

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

Pool

Kitchen

Charming Annapolis WaterVIEW Home

Annapolis MD

$714 nightly

$814 total

Jun 29 - Jun 30

Total with taxes and fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Hot Tub

Kitchen

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

Washer

Dryer

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD

With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.

Kitchen

Washer

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Stevensville MD

When you stay at this vacation home in Stevensville, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Cute, Cozy 2-bedroom house in near Annapolis with water access

Crownsville MD

$205 nightly

$233 total

Jun 22 - Jun 23

Total with taxes and fees

With a stay at this vacation home in Crownsville (Herald Harbor), you'll be a 4-minute drive from Joyces Marina and 9 minutes from Eisenhower Golf Course.

Kitchen

Washer

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$418 nightly

$477 total

Jun 17 - Jun 18

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 12 minutes from Sandy Point State Park.

Kitchen

Washer

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

Annapolis MD

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be a 2-minute drive from Chesapeake Bay and 6 minutes from Sandy Point State Park.

Pool

Kitchen

Lower Level Loft - Adorable Studio Apt. Near BWI

Millersville MD

$97 nightly

$111 total

Jul 14 - Jul 15

Total with taxes and fees

With a stay at this vacation home in Millersville (South Gate), you'll be within a 15-minute drive of Arundel Mills Mall and Maryland Live Casino.

Kitchen

Washer

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 15 minutes from Chesapeake Bay.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Kent Island

View all properties

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.