New Windsor Vacation Rentals

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Sep 27 - Sep 28
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Sep 28 - Sep 29
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Vacation Rentals in New Windsor

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (120)
"We LOVED our stay at Surrey Cabin! Quaint, clean, quiet, and the property is breathtaking! The bed was super comfortable and we had everything we needed. We will definitely be coming back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Round Top Campground
Cottage, 2 Bedrooms (Loft, No Pets) | WiFi

Round Top Campground

2.0 star property
9.0 out of 10, Wonderful, (21)
"Campground is short drive to many of Gettysburg's tours and museums. It also has structured activities for families/kids. And also hosts food trucks! "
Round Top Campground
Manor on the 7th Luxury minutes away from History
Pool

Manor on the 7th Luxury minutes away from History

9.8 out of 10, Exceptional, (16)
"We had a wonderful stay. The house is just a few minutes from the Gettysburg battlefield. We spent three days touring the battlefield and the house was perfect for relaxing and unwinding at the end of each busy day. "
Manor on the 7th Luxury minutes away from History
Birch Cabin at Hunting Creek Hideaway
Property grounds

Birch Cabin at Hunting Creek Hideaway

9.8 out of 10, Exceptional, (11)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is ￥12,781
￥20,679 total
includes taxes & fees
Oct 5 - Oct 6
Birch Cabin at Hunting Creek Hideaway
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Smart TV

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

9.8 out of 10, Exceptional, (19)
"This is an amazing place to stay its not far away from alot of things but gives you the sense of being in the middle of no where. "
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Fall is right around the corner! Plan your mountain getaway now!
Fridge, microwave, oven, stovetop

Fall is right around the corner! Plan your mountain getaway now!

10.0 out of 10, Exceptional, (306)
"We had a great time.The cabin was very clean and cozy. We loved using the fireplace!"
Fall is right around the corner! Plan your mountain getaway now!
Applewood Landing Sum
Pool

Applewood Landing Sum

10.0 out of 10, Exceptional, (6)
"Family of 9 had a great time at this beautiful home with room to spare! "
The price is ￥35,429
￥138,810 total
includes taxes & fees
Sep 29 - Sep 30
Applewood Landing Sum
*Luxury Condo In Downtown Frederick*
Smart TV

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (67)
"Great time. Everything was perfect and place was just what we needed. "
The price is ￥16,323
￥40,160 total
includes taxes & fees
Sep 29 - Sep 30
*Luxury Condo In Downtown Frederick*
Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick
Property grounds

Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick

9.8 out of 10, Exceptional, (29)
"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "
The price is ￥15,472
￥38,268 total
includes taxes & fees
Sep 29 - Sep 30
Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick
Countryside Manor |Porch, Firepit & Playset
Fridge, microwave, oven, stovetop

Countryside Manor |Porch, Firepit & Playset

2.0 star property
9.8 out of 10, Exceptional, (9)
"Very comfortable stay for our family! "
Countryside Manor |Porch, Firepit & Playset
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Interior

Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen

9.4 out of 10, Exceptional, (38)
"Great time, owner very attentive! Thank you!"
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
“The Train Depot” 2nd oldest in the US
Exterior

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (88)
"Beautiful property within walking distance of downtown "
“The Train Depot” 2nd oldest in the US
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, (48)
"Awesome place."
The price is ￥39,690
￥68,558 total
includes taxes & fees
Sep 28 - Sep 29
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
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, (4)
"Very nice place .Quiet and peaceful"
The price is ￥18,686
￥33,118 total
includes taxes & fees
Oct 2 - Oct 3
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
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, (115)
"Clean and comfortable, quiet and perfectly located, this the perfect place for enjoying downtown "
The price is ￥18,238
￥43,735 total
includes taxes & fees
Oct 6 - Oct 7
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!
Property grounds

4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!

10.0 out of 10, Exceptional, (143)
"We will be back! The guest house was perfect for us! "
4BR Cottage: Pool, Near Downtown, Heated Spa-Open Year Round, On-site Masseuse!
The Jarboe Suite on historic Manor House grounds!
Terrace/patio

The Jarboe Suite on historic Manor House grounds!

10.0 out of 10, Exceptional, (3)
"Has everything one needs. A little trouble with the heating system but the host was quick to respond. Would stay again. "
The Jarboe Suite on historic Manor House grounds!
A View of the Middletown Valley Like No Other
Outdoor dining

A View of the Middletown Valley Like No Other

9.6 out of 10, Exceptional, (23)
"Great location and accommodations. The host (Greg) lives next door and could not have been more responsive and helpful!"
A View of the Middletown Valley Like No Other
Farmhouse on River, 12 Miles to Liberty Mountain
House (5 Bedrooms) | Interior

Farmhouse on River, 12 Miles to Liberty Mountain

2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful property, excellent stay! "
Farmhouse on River, 12 Miles to Liberty Mountain
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!
House (3 Bedrooms) | Interior

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

3.0 star property
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!
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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Top New Windsor Hotel Reviews

Marriott Owings Mills Metro Centre

Marriott Owings Mills Metro Centre

10/10 Excellent
"The room was very clean and spacious. Despite not having a crib, I was able to move a couch over to ensure if my child rolled off the bed, they would not land on the floor. My only two minor issues were the covering over the peep hole on the door not staying up & the additional locks on the doors not working properly. A tad scary as a mother with her child alone, but overall it was a lovely stay & would gladly come back."
Becca 1-night trip
Posted 3 days ago
Marriott Owings Mills Metro Centre

Find out more about New Windsor

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

  • View our selection of featured holiday rentals in New Windsor
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  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

Look no further and take a look at our great range of rental properties in New Windsor!

Frequently asked questions

Can I find vacation rentals in New Windsor?

Yes, we give you a choice of vacation rentals near well known points of interest in New Windsor, or you can go with a more secluded option if you want a relaxing place to 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 vacation home rentals in New Windsor?

Applewood Landing Sum: Visitors like this New Windsor vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with an arcade game room and a 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 larger area, you’ll find Old Westminster Winery and Elk Run Vineyards.

What’s a vacation rental in New Windsor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in New Windsor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.