Search Vacation Homes in New Windsor

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Vacation Homes in New Windsor

Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Vacation Home in Frederick

10.0 out of 10, Exceptional, (34)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
$236 nightly
The price is $250
Dec 3 - Dec 4
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Smart TV
*Luxury Condo In Downtown Frederick*

Vacation Home in Downtown Frederick

9.0 out of 10, Wonderful, (69)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
$245 nightly
The price is $260
Dec 3 - Dec 4
Total with taxes and fees
*Luxury Condo In Downtown Frederick*
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Vacation Home in Downtown Frederick

9.4 out of 10, Exceptional, (119)
"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "
United States
Natalie C.
$273 nightly
The price is $289
Dec 3 - Dec 4
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Interior
New townhouse

Vacation Home in Frederick

9.4 out of 10, Exceptional, (9)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
$340 nightly
The price is $361
Dec 3 - Dec 4
Total with taxes and fees
New townhouse
Interior
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Vacation Home in Woodbine

$140 nightly
The price is $148
Dec 3 - Dec 4
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Outdoor spa tub
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

Vacation Home in Westminster

8.0 out of 10, Very Good, (1)
"The stay was nice and as advertised. It was a little noisy at night with the split house and close neighbors, but it was a nice place. "
United States
Payson D.
$316 nightly
The price is $335
Dec 3 - Dec 4
Total with taxes and fees
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Fridge, microwave, oven, stovetop
Historic Bucher House with central location to Gettysburg and Lancaster Amish

Vacation Home in Hanover

9.8 out of 10, Exceptional, (68)
"The house is very nice. Fun walking around and exploring the history in the house. I now want to install a shuffleboard court at my own home!"
United States
Adam P.
$308 nightly
The price is $340
Dec 3 - Dec 4
Total with taxes and fees
Historic Bucher House with central location to Gettysburg and Lancaster Amish
Pool
Applewood Landing

Vacation Home in Gettysburg

10.0 out of 10, Exceptional, (6)
"Perfect home for our family of 14 celebrating my mom’s 80th! Spacious kitchen with two dishwashers, great pool area, and plenty of room to gather. Loved the sunsets, outdoor amenities, and convenient location. Hosts were wonderful and responsive—highly recommend!"
United States
Anonymous traveler
$814 nightly
The price is $863
Dec 9 - Dec 10
Total with taxes and fees
Applewood Landing
Fridge, microwave, oven, stovetop
Newly constructed 6 bedroom home

Vacation Home in Frederick

10.0 out of 10, Exceptional, (14)
"This is our second time staying here and we really love how easily we all fit in. It's clean, family friendly, and have lots of space."
United States
Bonnie S.
$438 nightly
The price is $464
Dec 3 - Dec 4
Total with taxes and fees
Newly constructed 6 bedroom home
Fridge, microwave, oven, stovetop
Experience Elevated Comfort: Luxe Breeze Townhouse.

Vacation Home in Owings Mills

9.6 out of 10, Exceptional, (4)
"Awesome stay and great location. Very quiet neighborhood, made the stay comfortable and relaxing. Very spacious and modern. "
United States
Jesse H.
$497 nightly
The price is $574
Jan 1 - Jan 2, 2026
Total with taxes and fees
Experience Elevated Comfort: Luxe Breeze Townhouse.
Fridge, microwave, oven, stovetop
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby

Vacation Home in Frederick

8.0 out of 10, Very Good, (1)
"This was a great location for two families coming together for a wedding. The beds were comfortable, and the house was conveniently located within walking distance of a shopping plaza and close to the expressway on-ramp. The owner was quick to respond and helpful in answering any questions we had.Overall, the house met all our needs and provided a comfortable stay. It could use a few minor updates—like fresh paint on the scuffed walls—and some additional seating since it sleeps nine people....
United States
Heather P.
$328 nightly
The price is $348
Dec 7 - Dec 8
Total with taxes and fees
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
Fridge, microwave, oven, stovetop
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Vacation Home in Fairfield

9.8 out of 10, Exceptional, (49)
"Very nice home. Cozy and comfortable ."
United States
Angel C.
$416 nightly
The price is $459
Dec 3 - Dec 4
Total with taxes and fees
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fridge, microwave, oven, stovetop
Modern Suite with Private Bath – Stylish & Comfy

Vacation Home in Frederick

$160 nightly
The price is $170
Dec 3 - Dec 4
Total with taxes and fees
Modern Suite with Private Bath – Stylish & Comfy
Terrace/patio
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

Vacation Home in Gaithersburg

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property is, without question, one of the finest vacation rentals I have ever experienced. I was searching for a family-friendly space suitable for hosting a dinner, and this home exceeded all expectations. The photos do not fully capture its beauty. Ms. Mohammed was an exceptional host—responsive, professional, and clearly dedicated to maintaining a high standard of hospitality.Backyard: The outdoor area is stunning—featuring a firepit, grill, swing set, zipline, and multiple seating areas...
United States
Asher C.
$794 nightly
The price is $897
Dec 3 - Dec 4
Total with taxes and fees
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Terrace/patio
Charming 3-bedroom house in the heart of town right off I-70

Vacation Home in Mount Airy

9.8 out of 10, Exceptional, (6)
"perfect location in mount airy, walk to restaurants, etc. Great communications with owner and super clean updated home."
United States
Michael H.
$481 nightly
The price is $510
Dec 26 - Dec 27
Total with taxes and fees
Charming 3-bedroom house in the heart of town right off I-70
Fridge, microwave, oven, stovetop
Charming 4-bedroom house with WiFi and AC in historic Gettysburg

Vacation Home in Gettysburg

10.0 out of 10, Exceptional, (2)
"Wonderful first experience with VRBO. Our hosts were very friendly and made our stay comfortable. "
United States
Janis O.
$486 nightly
The price is $536
Dec 4 - Dec 5
Total with taxes and fees
Charming 4-bedroom house with WiFi and AC in historic Gettysburg
Interior
Private Guest House - Please note does NOT sleeps 30

Vacation Home in Reisterstown

6.8 out of 10, (3)
"Providing a better equipped kitchen will improve this listing for future guests."
United States
Jennifer M.
$508 nightly
The price is $587
Dec 31 - Jan 1, 2026
Total with taxes and fees
Private Guest House - Please note does NOT sleeps 30
Microwave, stovetop, dishwasher
The blissful house in Howard County with 3 bedrooms 3 bathrooms.

Vacation Home in Marriottsville

$802 nightly
The price is $850
Dec 3 - Dec 4
Total with taxes and fees
The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Living area
Cozy Guesthouse in Woodstock, MD

Vacation Home in Woodstock

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."
United States
Marie E M.
$201 nightly
The price is $232
Dec 3 - Dec 4
Total with taxes and fees
Cozy Guesthouse in Woodstock, MD
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

Inn at Cemetery Hill

Inn at Cemetery Hill

10/10 Excellent
"Everything was excellent "
Carlina 3-night trip
Posted 1 day ago
Inn at Cemetery Hill

Find out more about New Windsor

New Windsor Vacation Homes information

Number of reviews
376
Accommodation
109 Vacation Homes
Lowest Price
$148
Highest Price
$897

Explore a world of travel with Expedia