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Check prices for these dates

Tonight
26 Jun - 27 Jun
Tomorrow
27 Jun - 28 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Holiday Rentals in New Windsor

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Exterior

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (104)
"Cozy cabin, wonderful hosts, great location near the AT. Probably the most thoughtful host we’ve had, they’ve thought of everything from breakfast treats and extra linens, even dog treats."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Manor on the 7th Luxury minutes away from History
Pool

Manor on the 7th Luxury minutes away from History

10.0 out of 10, Exceptional, (13)
"The house, property, and overall experience were top notch. Highly recommend. "
Manor on the 7th Luxury minutes away from History
“The Train Depot” 2nd oldest in the US
Exterior

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (81)
"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "
“The Train Depot” 2nd oldest in the US
Birch Cabin at Hunting Creek Hideaway
1 bedroom, bed sheets

Birch Cabin at Hunting Creek Hideaway

9.4 out of 10, Exceptional, (3)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is £112
includes taxes & fees
9 Jul - 10 Jul
Birch Cabin at Hunting Creek Hideaway
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

9.4 out of 10, Exceptional, (109)
"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"
The price is £220
includes taxes & fees
1 Jul - 2 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
*Modern Condo In Downtown Frederick*
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (60)
"Great stay "
The price is £199
includes taxes & fees
29 Jun - 30 Jun
*Modern Condo In Downtown Frederick*
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Miscellaneous

A newly renovated, pet-friendly Penthouse condo with private rooftop deck.

9.6 out of 10, Exceptional, (44)
"Great location to Old Town. "
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
*Luxury Condo In Downtown Frederick*
Smart TV

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (62)
"The condo is quite spacious, more than expected. We enjoyed the modern touches and private parking is a big plus in downtown Frederick. So close to Carroll Creek and Market St. The hosts are responsive. We highly recommend staying at Gideon Getaways! "
The price is £251
includes taxes & fees
30 Jun - 1 Jul
*Luxury Condo In Downtown Frederick*
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

10.0 out of 10, Exceptional, (1)
"We truly loved this little cottage and was perfect for our stay while visiting family and friends. We took several walks in the area, enjoyed the quiet and the adorable space. The beds were very comfortable. The cottage was very clean and nicely remodeled. We will hopefully be able to rent here again at our next visit! Owner was very responsive and helpful as well. Only was missing a blowdryer, but I improvised! "
The price is £150
includes taxes & fees
2 Jul - 3 Jul
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Gorgeous 1840 Log Cabin- Downtown
Fridge, microwave, oven, stovetop

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (134)
"The location is perfect to all that downtown Frederick has to offer. The house is charming and the beds are very comfortable. The host responds very quickly to any questions."
Gorgeous 1840 Log Cabin- Downtown
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fridge, microwave, oven, stovetop

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (46)
"Awesome place."
The price is £318
includes taxes & fees
1 Jul - 2 Jul
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Smart TV

Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (10)
"A nice quiet place to get away for a few days and visit the Gettysburg Museum and battle fields "
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Cozy Guesthouse in Woodstock, MD
Property grounds

Cozy Guesthouse in Woodstock, MD

2.0 out of 10, (1)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
The price is £155
includes taxes & fees
27 Jun - 28 Jun
Cozy Guesthouse in Woodstock, MD
Quiet Apartment in Coolest Small Town in America!
Exterior

Quiet Apartment in Coolest Small Town in America!

9.4 out of 10, Exceptional, (45)
"We enjoyed our stay!"
Quiet Apartment in Coolest Small Town in America!
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (71)
"Location was great! Felt safe and check in was really easy."
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Welcome to our serene Horse Farm, a getaway to nature outside of Washington, DC.
Miscellaneous

Welcome to our serene Horse Farm, a getaway to nature outside of Washington, DC.

10.0 out of 10, Exceptional, (6)
Welcome to our serene Horse Farm, a getaway to nature outside of Washington, DC.
The GRACE Villa - a homey affair!
Interior

The GRACE Villa - a homey affair!

9.0 out of 10, Wonderful, (16)
"2nd year staying at this property for our conference. It was just as great ascthe last time. This is our go to place when we are in the area."
The GRACE Villa - a homey affair!
3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg
Fridge, microwave, oven, stovetop

3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg

10.0 out of 10, Exceptional, (300)
"We've stayed here multiple times and always have a great time. Very close to Liberty for skiing. Always good communication with the owner and the cabin is cozy and well-stocked. Highly recommend!"
3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Property grounds

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

10.0 out of 10, Exceptional, (139)
"Very well decorated. The owners were very attentive and kind. Left a candle with wine in the bedrooms. Very well set up and beautiful!!"
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Cozy out of the way studio retreat with AC and WiFi in charming Westminster
Property grounds

Cozy out of the way studio retreat with AC and WiFi in charming Westminster

10.0 out of 10, Exceptional, (4)
"Great instructions, kind host, great stay!"
The price is £119
includes taxes & fees
30 Jun - 1 Jul
Cozy out of the way studio retreat with AC and WiFi in charming Westminster
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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Frequently asked questions

Can I find holiday rentals in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more secluded option if you're looking for a relaxing stay. New Windsor is known for its shopping and wineries. Make sure you have time to check out the restaurants and university setting during your trip.

What are some of the best holiday rentals that New Windsor has to offer?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This holiday home rental outside of New Windsor is located in the city centre, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in New Windsor?

While exploring the area, visit family-friendly sights like Adventure Park USA, or get outside and enjoy nature at Union Mills Homestead Park. In the wider area, you’ll find Old Westminster Winery and Elk Run Vineyards.

What’s a holiday rental in New Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in New Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for small groups.