Book Holiday Homes in New Windsor

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 New Windsor

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*

Frederick
The price is AU$419 per night from 3 Apr to 4 Apr
AU$419
includes taxes & fees
3 Apr - 4 Apr
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 5 minutes by foot from City of Frederick Dog ...
*Luxury Condo In Downtown Frederick*
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Frederick
The price is AU$499 per night from 6 Apr to 7 Apr
AU$499
includes taxes & fees
6 Apr - 7 Apr
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 5 minutes by foot from National Museum of Civil War ...
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

Frederick
A stay at this vacation home places you in the heart of Frederick, within a 15-minute walk of Carroll Creek Linear Park and Roads and Rails Museum.
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Save an average of 15% on thousands of hotels when you're signed in
“The Train Depot” 2nd oldest in the US

“The Train Depot” 2nd oldest in the US

Frederick
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 4 minutes by foot from National Museum of Civil War ...
“The Train Depot” 2nd oldest in the US
Applewood Landing Sum

Applewood Landing Sum

Gettysburg
The price is AU$1,102 per night from 8 Apr to 9 Apr
AU$1,102
includes taxes & fees
8 Apr - 9 Apr
Located in Gettysburg, this vacation home is in a rural location, within a 10-minute drive of Gettysburg National Military Park and Lincoln's Lost Treasure.
Applewood Landing Sum
The GRACE Villa - a homey affair!

The GRACE Villa - a homey affair!

Reisterstown
Located in Reisterstown, this vacation home is a 4-minute drive from BARC Park and 5 minutes from Foundry Row.
The GRACE Villa - a homey affair!
Gorgeous 1840 Log Cabin- Downtown

Gorgeous 1840 Log Cabin- Downtown

Frederick
With a stay at this vacation home, you'll be centrally located in Frederick, just a 4-minute walk from Frederick Memorial Hospital and 9 minutes by foot from ...
Gorgeous 1840 Log Cabin- Downtown
New townhouse

New townhouse

Frederick
With a stay at this vacation home in Frederick, you'll be within a 5-minute drive of Carroll Creek Linear Park and Roads and Rails Museum.
New townhouse
Manor on the 7th Luxury minutes away from History

Manor on the 7th Luxury minutes away from History

Gettysburg
Located in Gettysburg, this vacation home is in a rural location, within a 15-minute drive of Taneytown Memorial Park and Little Round Top.
Manor on the 7th Luxury minutes away from History
Don't see what you're looking for?
See all available properties in New Windsor
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.

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

Holiday houses in New Windsor 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 New Windsor 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 New Windsor adventures, obvs.

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

New Windsor Holiday Homes essential information

Accommodation
99 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$1,102
Popular accommodation
*Luxury Condo In Downtown Frederick*, RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome
, “The Train Depot” 2nd oldest in the US, Applewood Landing Sum, The GRACE Villa - a homey affair!, Gorgeous 1840 Log Cabin- Downtown, New townhouse, Manor on the 7th Luxury minutes away from History

Top trending hotels in New Windsor

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

3 out of 5
4730 Painters Mill Rd, Owings Mills, MD
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 13 Apr to 14 Apr
AU$186
includes taxes & fees
13 Apr - 14 Apr
Located in Owings Mills, Hyatt Place Baltimore/Owings Mills is in the business district, a 2-minute drive from Foundry Row and 6 minutes from Under Armour Performance ...
Hyatt Place Baltimore/Owings Mills
Inn at Cemetery Hill

Inn at Cemetery Hill

2 out of 5
613 Baltimore St, Gettysburg, PA
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 16 Apr to 17 Apr
AU$265
includes taxes & fees
16 Apr - 17 Apr
Located in Gettysburg (Gettysburg Historic District), Inn at Cemetery Hill is within a 10-minute walk of Gettysburg Battlefield Museum and Gettysburg National ...
Inn at Cemetery Hill
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is AU$137 per night from 17 Apr to 18 Apr
AU$137
includes taxes & fees
17 Apr - 18 Apr
A stay at Country Inn & Suites by Radisson, Frederick, MD places you in the heart of Frederick, just a 5-minute walk from Francis Scott Key Mall and within a ...
Country Inn & Suites by Radisson, Frederick, MD
Save an average of 15% on thousands of hotels when you're signed in
Comfort Suites Near Gettysburg Battlefield Visitor Center

Comfort Suites Near Gettysburg Battlefield Visitor Center

2.5 out of 5
945 Baltimore Pike, Gettysburg, PA
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 20 Apr to 21 Apr
AU$159
includes taxes & fees
20 Apr - 21 Apr
A stay at Comfort Suites Near Gettysburg Battlefield Visitor Center places you in the heart of Gettysburg, within a 10-minute walk of Gettysburg Battlefield ...
Comfort Suites Near Gettysburg Battlefield Visitor Center
Don't see what you're looking for?
See all available properties in New Windsor
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.