Chester Vacation Rentals
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Vacation Rentals in Chester
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis MD
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
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
$518 nightly
The price is $591 total per night
$591 total
Jun 14 - Jun 15
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
$204 nightly
The price is $232 total per night
$232 total
Jun 14 - Jun 15
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.
Cozy 2br home w/ parking in downtown Annapolis
Annapolis MD
$416 nightly
The price is $474 total per night
$474 total
Jun 17 - Jun 18
Total with taxes and fees
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of Annapolis City Dock and U.S. Naval Academy.
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
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Annapolis MD
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of Annapolis City Dock and U.S. Naval Academy.
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.
Chester Vacation Rentals essential information
Accommodation | 648 Vacation Rentals |
|---|---|
Lowest Price | $232 |
Highest Price | $591 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Private Pool & Stunning Bay Views on Kent Island, Charming Annapolis WaterVIEW Home, Grace Cottage, St Michaels Walk to everything!, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly, Cute, Cozy 2-bedroom house in near Annapolis with water access, Cozy 2br home w/ parking in downtown Annapolis, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Charming Historic Annapolis Home With Two Off-street Parking Places!, Eastport Cottage .5 mi from Downtown Annapolis |