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Our top choices for New Windsor vacation homes

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Westminster
9.0 out of 10, Wonderful, (2)
"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.
The price is AEDĀ 463
AEDĀ 1,230 total
includes taxes & fees
12 Dec - 13 Dec
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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.
The price is AEDĀ 408
AEDĀ 1,016 total
includes taxes & fees
14 Dec - 15 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (71)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is AEDĀ 375
AEDĀ 954 total
includes taxes & fees
14 Dec - 15 Dec
*Luxury Condo In Downtown Frederick*

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

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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.
The price is AEDĀ 404
AEDĀ 966 total
includes taxes & fees
4 Jan - 5 January 2026
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
The price is AEDĀ 367
AEDĀ 545 total
includes taxes & fees
20 Dec - 21 Dec
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

New townhouse

New townhouse
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.
The price is AEDĀ 555
AEDĀ 1,305 total
includes taxes & fees
15 Dec - 16 Dec
New townhouse

Historic Bucher House with central location to Gettysburg and Lancaster Amish

Historic Bucher House with central location to Gettysburg and Lancaster Amish
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.
The price is AEDĀ 988
AEDĀ 1,233 total
includes taxes & fees
14 Dec - 15 Dec
Historic Bucher House with central location to Gettysburg and Lancaster Amish

Applewood Landing

Applewood Landing
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
The price is AEDĀ 643
AEDĀ 3,103 total
includes taxes & fees
16 Dec - 17 Dec
Applewood Landing

Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes
Ijamsville
10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
The price is AEDĀ 918
AEDĀ 1,331 total
includes taxes & fees
3 Jan - 4 January 2026
Cozy Peaceful Basement Cabin Vibes

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
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.
The price is AEDĀ 782
AEDĀ 1,697 total
includes taxes & fees
11 Jan - 12 January 2026
Newly constructed 6 bedroom home

Experience Elevated Comfort: Luxe Breeze Townhouse.

Experience Elevated Comfort: Luxe Breeze Townhouse.
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.
The price is AEDĀ 698
AEDĀ 2,083 total
includes taxes & fees
5 Jan - 6 January 2026
Experience Elevated Comfort: Luxe Breeze Townhouse.

Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby

Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
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.
The price is AEDĀ 507
AEDĀ 1,265 total
includes taxes & fees
16 Dec - 17 Dec
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (14)
"Beautiful home with all desired ammenaties and very professional owners"
United States
Lawrence S.
The price is AEDĀ 786
AEDĀ 1,331 total
includes taxes & fees
26 Dec - 27 Dec
Chic, pets, walk to downtown

Countryside Manor |Porch, Firepit & Playset

Countryside Manor |Porch, Firepit & Playset
2.0 star property
Littlestown
9.8 out of 10, Exceptional, (9)
"Lovely well equipped house. Very quiet area. Enjoyed the corn hole and fire pit. Highly recommend this house. Perfect for our Gettysburg Battlefield trip. "
United States
Sharon M.
The price is AEDĀ 1,043
AEDĀ 2,630 total
includes taxes & fees
1 Jan - 2 January 2026
Countryside Manor |Porch, Firepit & Playset

Secret' Desires-Adult Only

Secret' Desires-Adult Only
2.0 star property
Gaithersburg
The price is AEDĀ 918
AEDĀ 1,913 total
includes taxes & fees
11 Jan - 12 January 2026
Secret' Desires-Adult Only

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

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (49)
"Very nice home. Cozy and comfortable ."
United States
Angel C.
The price is AEDĀ 975
AEDĀ 1,684 total
includes taxes & fees
14 Dec - 15 Dec
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Modern Suite with Private Bath – Stylish & Comfy

Modern Suite with Private Bath – Stylish & Comfy
Frederick
The price is AEDĀ 514
AEDĀ 623 total
includes taxes & fees
16 Dec - 17 Dec
Modern Suite with Private Bath – Stylish & Comfy

Charming 3-bedroom house in the heart of town right off I-70

Charming 3-bedroom house in the heart of town right off I-70
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.
The price is AEDĀ 922
AEDĀ 1,873 total
includes taxes & fees
26 Dec - 27 Dec
Charming 3-bedroom house in the heart of town right off I-70

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
2.0 star property
Gaithersburg
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.
The price is AEDĀ 1,322
AEDĀ 3,295 total
includes taxes & fees
14 Dec - 15 Dec
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

Charming 4-bedroom house with WiFi and AC in historic Gettysburg

Charming 4-bedroom house with WiFi and AC in historic Gettysburg
Gettysburg
10.0 out of 10, Exceptional, (3)
"Very clean home, quiet neighborhood, and close to town. The blueberry muffins were an added delight"
United States
Gail D.
The price is AEDĀ 1,285
AEDĀ 1,970 total
includes taxes & fees
14 Dec - 15 Dec
Charming 4-bedroom house with WiFi and AC in historic Gettysburg
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