Book Holiday Homes in Chester

Featured Holiday Homes in Chester

Dollhouse in Central Historic St Michaels

St Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and ...

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PERFECT LOCATION in the heart of history

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.

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

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 14 minutes from Chesapeake Bay.

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The Blue Crab Beach House - Free beach passes

North Beach MD

When you stay at this vacation home in North Beach, you'll be by the sea, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.

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"La Licorne" Waterfront Beach Cottage

North Beach MD

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

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Private Cottage on gated estate

Annapolis MD

With a stay at this vacation home in Annapolis, you'll be within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

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Charming Annapolis WaterVIEW Home

Annapolis MD

AU$828

26 May - 27 May

includes taxes & fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Annapolis MD

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 Chesapeake Bay ...

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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

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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 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	654 Holiday Homes
Lowest Price	AU$179
Highest Price	AU$828
Popular accommodation	Dollhouse in Central Historic St Michaels, PERFECT LOCATION in the heart of history, Charming Historic Annapolis Home With Two Off-street Parking Places!, The Blue Crab Beach House - Free beach passes , "La Licorne" Waterfront Beach Cottage, Private Cottage on gated estate, Charming Annapolis WaterVIEW Home, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Top trending hotels in Chester

Waterfront Sunset Bayview: sleeps 6

Chester MD

With a stay at this vacation home in Chester, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Exploration Center.

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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD

With a stay at this vacation home in Chester, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Exploration Center.

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DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

AU$179

24 May - 25 May

includes taxes & fees

When you stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 15-minute drive of U.S. Naval Academy and Chesapeake ...

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Historic Inns of Annapolis

58 State Circle Annapolis MD

Fully refundableReserve now, pay when you stay

AU$241

25 May - 26 May

includes taxes & fees

With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.

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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.

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