Book Holiday Homes in Queenstown

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Featured Holiday Homes in Queenstown

PERFECT LOCATION in the heart of history

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.
Opens in a new windowPERFECT LOCATION in the heart of history
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall MD
The price is AU$424 per night from 15 May to 16 May
AU$424
15 May - 16 May
includes taxes & fees
With a stay at this vacation home in Rock Hall, you'll be within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowBAYSIDE BUNGALOW
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

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.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
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Charming Historic Annapolis Home With Two Off-street Parking Places!

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.
Opens in a new windowCharming Historic Annapolis Home With Two Off-street Parking Places!
Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach

Stevensville MD
The price is AU$1,687 per night from 18 May to 19 May
AU$1,687
18 May - 19 May
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowKent Island Luxary Home W/ Pool and walking distance from the beach
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD
The price is AU$420 per night from 17 May to 18 May
AU$420
17 May - 18 May
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowRelax on Kent Island in a 4 Bedroom Home w/Waterview!
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

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.
Opens in a new windowLovely bay views with kayaks, bikes, fire pit, crabbing & more
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

St. Michaels MD
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of St Michaels Nature Trail and Higgins Yacht Yard and Marina.
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

Easton MD
Located in Easton, this vacation home is within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.
Opens in a new window“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
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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.

Queenstown 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 Queenstown vacation homes are the perfect way for you to wing it.

Holiday houses in Queenstown 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 Queenstown 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 Queenstown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Queenstown 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 Queenstown 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.

Queenstown Holiday Homes essential information

Accommodation
594 Holiday Homes
Lowest Price
AU$173
Highest Price
AU$1,687
Popular accommodation
PERFECT LOCATION in the heart of history, BAYSIDE BUNGALOW, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Charming Historic Annapolis Home With Two Off-street Parking Places!, Kent Island Luxary Home W/ Pool and walking distance from the beach, Relax on Kent Island in a 4 Bedroom Home w/Waterview!, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock, “It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

Top trending hotels in Queenstown

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis

Queenstown MD
Located in Queenstown, this farm stay is in a rural location, within a 15-minute drive of Queenstown Premium Outlets and Rufus M and Loraine Hall Todd Performing ...
Opens in a new windowRelax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$230 per night from 8 June to 9 June
AU$230
8 June - 9 June
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.
Opens in a new windowHistoric Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 31 May to 1 June
AU$179
31 May - 1 June
includes taxes & fees
With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta ...
Opens in a new windowDoubleTree by Hilton Hotel Annapolis
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Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is AU$173 per night from 24 May to 25 May
AU$173
24 May - 25 May
includes taxes & fees
Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
Opens in a new windowCrowne Plaza Annapolis by IHG
Don't see what you're looking for?
See all available properties in Queenstown
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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.

Top Picks

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^Subject to availability and chosen travel dates.