We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in New Windsor

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
48 rentals in New Windsor.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel., holiday rental in New Windsor
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel., holiday rental in New Windsor
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel., holiday rental in New Windsor

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location, holiday rental in New Windsor
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location, holiday rental in New Windsor
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location, holiday rental in New Windsor

Beautiful Cozy 2 br in-law apt, prime Hudson Valley location

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres, holiday rental in New Windsor
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres, holiday rental in New Windsor
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres, holiday rental in New Windsor

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The following properties within 32 kms of New Windsor match all your filters:
Cozy victorian getaway, holiday rental in New Windsor
Cozy victorian getaway, holiday rental in New Windsor
Cozy victorian getaway, holiday rental in New Windsor

Cozy victorian getaway

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Deck View of Hudson River & Mt Beacon - Boho Suite, holiday rental in New Windsor
Deck View of Hudson River & Mt Beacon - Boho Suite, holiday rental in New Windsor
Deck View of Hudson River & Mt Beacon - Boho Suite, holiday rental in New Windsor

Deck View of Hudson River & Mt Beacon - Boho Suite

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Grant - A Tranquil One Bedroom Steps from River, holiday rental in New Windsor
Grant - A Tranquil One Bedroom Steps from River, holiday rental in New Windsor
Grant - A Tranquil One Bedroom Steps from River, holiday rental in New Windsor

Grant - A Tranquil One Bedroom Steps from River

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
#4 Quaint 1 bedroom apartment in Historic Building, holiday rental in New Windsor
#4 Quaint 1 bedroom apartment in Historic Building, holiday rental in New Windsor
#4 Quaint 1 bedroom apartment in Historic Building, holiday rental in New Windsor

#4 Quaint 1 bedroom apartment in Historic Building

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Tiffany Suite: Enclosed Solarium Room + Bedroom + Office/Yoga Room, holiday rental in New Windsor
Tiffany Suite: Enclosed Solarium Room + Bedroom + Office/Yoga Room, holiday rental in New Windsor
Tiffany Suite: Enclosed Solarium Room + Bedroom + Office/Yoga Room, holiday rental in New Windsor

Tiffany Suite: Enclosed Solarium Room + Bedroom + Office/Yoga Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
#2, Quaint Private Apartment in Historic Building, holiday rental in New Windsor
#2, Quaint Private Apartment in Historic Building, holiday rental in New Windsor
#2, Quaint Private Apartment in Historic Building, holiday rental in New Windsor

#2, Quaint Private Apartment in Historic Building

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
#3, 3rd Flr Studio Apartment in Historic Building, holiday rental in New Windsor
#3, 3rd Flr Studio Apartment in Historic Building, holiday rental in New Windsor
#3, 3rd Flr Studio Apartment in Historic Building, holiday rental in New Windsor

#3, 3rd Flr Studio Apartment in Historic Building

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
"GRAND ON THE HUDSON" - Executive Suites/3rd FL, holiday rental in New Windsor
"GRAND ON THE HUDSON" - Executive Suites/3rd FL, holiday rental in New Windsor
"GRAND ON THE HUDSON" - Executive Suites/3rd FL, holiday rental in New Windsor

"GRAND ON THE HUDSON" - Executive Suites/3rd FL

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hudson River Retreat, holiday rental in New Windsor
Hudson River Retreat, holiday rental in New Windsor
Hudson River Retreat, holiday rental in New Windsor

Hudson River Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
#1, Studio Apartment in Historic Building, holiday rental in New Windsor
#1, Studio Apartment in Historic Building, holiday rental in New Windsor
#1, Studio Apartment in Historic Building, holiday rental in New Windsor

#1, Studio Apartment in Historic Building

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beacon Apt w/ Patio + Grill; Walk to Main St!, holiday rental in New Windsor
Beacon Apt w/ Patio + Grill; Walk to Main St!, holiday rental in New Windsor
Beacon Apt w/ Patio + Grill; Walk to Main St!, holiday rental in New Windsor

Beacon Apt w/ Patio + Grill; Walk to Main St!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Scenic 1-bedroom rental in Newburgh, holiday rental in New Windsor
Scenic 1-bedroom rental in Newburgh, holiday rental in New Windsor
Scenic 1-bedroom rental in Newburgh, holiday rental in New Windsor

Scenic 1-bedroom rental in Newburgh

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic Hudson Valley Apartment: River View!, holiday rental in New Windsor
Historic Hudson Valley Apartment: River View!, holiday rental in New Windsor
Historic Hudson Valley Apartment: River View!, holiday rental in New Windsor

Historic Hudson Valley Apartment: River View!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hot Tub Bliss with King Master Bedroom, holiday rental in New Windsor
Hot Tub Bliss with King Master Bedroom, holiday rental in New Windsor
Hot Tub Bliss with King Master Bedroom, holiday rental in New Windsor

Hot Tub Bliss with King Master Bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
A luxurious stay., holiday rental in New Windsor
A luxurious stay., holiday rental in New Windsor
A luxurious stay., holiday rental in New Windsor

A luxurious stay.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Guests state the home is charming. New central air conditioning., holiday rental in New Windsor
Guests state the home is charming. New central air conditioning., holiday rental in New Windsor
Guests state the home is charming. New central air conditioning., holiday rental in New Windsor

Guests state the home is charming. New central air conditioning.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming Hudson River Valley Vacation Rental!, holiday rental in New Windsor
Charming Hudson River Valley Vacation Rental!, holiday rental in New Windsor
Charming Hudson River Valley Vacation Rental!, holiday rental in New Windsor

Charming Hudson River Valley Vacation Rental!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
MidCentury Modern Suite with Hudson River/Mt Beacon Views, holiday rental in New Windsor
MidCentury Modern Suite with Hudson River/Mt Beacon Views, holiday rental in New Windsor
MidCentury Modern Suite with Hudson River/Mt Beacon Views, holiday rental in New Windsor

MidCentury Modern Suite with Hudson River/Mt Beacon Views

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Home Historical District, holiday rental in New Windsor
Beautiful Home Historical District, holiday rental in New Windsor
Beautiful Home Historical District, holiday rental in New Windsor

Beautiful Home Historical District

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Newburgh, New York, Vacation Rental!, holiday rental in New Windsor
Newburgh, New York, Vacation Rental!, holiday rental in New Windsor
Newburgh, New York, Vacation Rental!, holiday rental in New Windsor

Newburgh, New York, Vacation Rental!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Modern 2BR in Staten Island, holiday rental in New Windsor
Modern 2BR in Staten Island, holiday rental in New Windsor
Modern 2BR in Staten Island, holiday rental in New Windsor

Modern 2BR in Staten Island

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic 1800's Cornwall-On-Hudson Cottage!, holiday rental in New Windsor
Historic 1800's Cornwall-On-Hudson Cottage!, holiday rental in New Windsor
Historic 1800's Cornwall-On-Hudson Cottage!, holiday rental in New Windsor

Historic 1800's Cornwall-On-Hudson Cottage!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Bright Cornwall-On-Hudson Vacation Rental!, holiday rental in New Windsor
Bright Cornwall-On-Hudson Vacation Rental!, holiday rental in New Windsor
Bright Cornwall-On-Hudson Vacation Rental!, holiday rental in New Windsor

Bright Cornwall-On-Hudson Vacation Rental!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Spacious Colonial with ample space, holiday rental in New Windsor
Spacious Colonial with ample space, holiday rental in New Windsor
Spacious Colonial with ample space, holiday rental in New Windsor

Spacious Colonial with ample space

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stylish & Spacious House w/ Hudson River Views, holiday rental in New Windsor
Stylish & Spacious House w/ Hudson River Views, holiday rental in New Windsor
Stylish & Spacious House w/ Hudson River Views, holiday rental in New Windsor

Stylish & Spacious House w/ Hudson River Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy Cottage minutes to West Point, holiday rental in New Windsor
Cozy Cottage minutes to West Point, holiday rental in New Windsor
Cozy Cottage minutes to West Point, holiday rental in New Windsor

Cozy Cottage minutes to West Point

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful 1850's brick farmhouse in Beacon - 4 bdrm, 2 1/2 bath, entire house., holiday rental in New Windsor
Beautiful 1850's brick farmhouse in Beacon - 4 bdrm, 2 1/2 bath, entire house., holiday rental in New Windsor
Beautiful 1850's brick farmhouse in Beacon - 4 bdrm, 2 1/2 bath, entire house., holiday rental in New Windsor

Beautiful 1850's brick farmhouse in Beacon - 4 bdrm, 2 1/2 bath, entire house.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic Cottage with View on the Hudson River, holiday rental in New Windsor
Historic Cottage with View on the Hudson River, holiday rental in New Windsor
Historic Cottage with View on the Hudson River, holiday rental in New Windsor

Historic Cottage with View on the Hudson River

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Victorian house with amazing Hudson River view, holiday rental in New Windsor
Victorian house with amazing Hudson River view, holiday rental in New Windsor
Victorian house with amazing Hudson River view, holiday rental in New Windsor

Victorian house with amazing Hudson River view

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Renovated 1850's Cottage on Storm King Mountain, holiday rental in New Windsor
Renovated 1850's Cottage on Storm King Mountain, holiday rental in New Windsor
Renovated 1850's Cottage on Storm King Mountain, holiday rental in New Windsor

Renovated 1850's Cottage on Storm King Mountain

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
River & Mountain Views - Hot Tub - Arcade - Pool Table - Bar, holiday rental in New Windsor
River & Mountain Views - Hot Tub - Arcade - Pool Table - Bar, holiday rental in New Windsor
River & Mountain Views - Hot Tub - Arcade - Pool Table - Bar, holiday rental in New Windsor

River & Mountain Views - Hot Tub - Arcade - Pool Table - Bar

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stunning historic Victorian house in Newburgh, holiday rental in New Windsor
Stunning historic Victorian house in Newburgh, holiday rental in New Windsor
Stunning historic Victorian house in Newburgh, holiday rental in New Windsor

Stunning historic Victorian house in Newburgh

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beacon Retreat with Hudson River views and access to hiking trails and downtown!, holiday rental in New Windsor
Beacon Retreat with Hudson River views and access to hiking trails and downtown!, holiday rental in New Windsor
Beacon Retreat with Hudson River views and access to hiking trails and downtown!, holiday rental in New Windsor

Beacon Retreat with Hudson River views and access to hiking trails and downtown!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Withers Mansion Large Groups - Hudson River Views!, holiday rental in New Windsor
Withers Mansion Large Groups - Hudson River Views!, holiday rental in New Windsor
Withers Mansion Large Groups - Hudson River Views!, holiday rental in New Windsor

Withers Mansion Large Groups - Hudson River Views!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
"The Big House" with Hudson River Views, holiday rental in New Windsor
"The Big House" with Hudson River Views, holiday rental in New Windsor
"The Big House" with Hudson River Views, holiday rental in New Windsor

"The Big House" with Hudson River Views

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Lander Pied-à-terre - pet friendly apartment in Historic Newburgh., holiday rental in New Windsor
The Lander Pied-à-terre - pet friendly apartment in Historic Newburgh., holiday rental in New Windsor
The Lander Pied-à-terre - pet friendly apartment in Historic Newburgh., holiday rental in New Windsor

The Lander Pied-à-terre - pet friendly apartment in Historic Newburgh.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Modern and Bright with office+ walk to nearby Waterfront, 1st FL., holiday rental in New Windsor
Modern and Bright with office+ walk to nearby Waterfront, 1st FL., holiday rental in New Windsor
Modern and Bright with office+ walk to nearby Waterfront, 1st FL., holiday rental in New Windsor

Modern and Bright with office+ walk to nearby Waterfront, 1st FL.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic British Arts & Crafts Garden Cottage on the Hudson, holiday rental in New Windsor
Historic British Arts & Crafts Garden Cottage on the Hudson, holiday rental in New Windsor
Historic British Arts & Crafts Garden Cottage on the Hudson, holiday rental in New Windsor

Historic British Arts & Crafts Garden Cottage on the Hudson

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
The Overlook 350- Where Family and Friends Retreat, holiday rental in New Windsor
The Overlook 350- Where Family and Friends Retreat, holiday rental in New Windsor
The Overlook 350- Where Family and Friends Retreat, holiday rental in New Windsor

The Overlook 350- Where Family and Friends Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Simple Modern Elegance with Hudson Valley Mountains backdrop, 3rd Fl, holiday rental in New Windsor
Simple Modern Elegance with Hudson Valley Mountains backdrop, 3rd Fl, holiday rental in New Windsor
Simple Modern Elegance with Hudson Valley Mountains backdrop, 3rd Fl, holiday rental in New Windsor

Simple Modern Elegance with Hudson Valley Mountains backdrop, 3rd Fl

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming newly renovated 2-bedroom house in the village of Cornwall-on-Hudson, holiday rental in New Windsor
Charming newly renovated 2-bedroom house in the village of Cornwall-on-Hudson, holiday rental in New Windsor
Charming newly renovated 2-bedroom house in the village of Cornwall-on-Hudson, holiday rental in New Windsor

Charming newly renovated 2-bedroom house in the village of Cornwall-on-Hudson

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley., holiday rental in New Windsor
Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley., holiday rental in New Windsor
Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley., holiday rental in New Windsor

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Modern Modest Design  Newburgh, Beacon, Westpoint  2nd. FL Apt., holiday rental in New Windsor
Modern Modest Design  Newburgh, Beacon, Westpoint  2nd. FL Apt., holiday rental in New Windsor
Modern Modest Design  Newburgh, Beacon, Westpoint  2nd. FL Apt., holiday rental in New Windsor

Modern Modest Design Newburgh, Beacon, Westpoint 2nd. FL Apt.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Historic Newburgh Home w/ Hudson River Views!, holiday rental in New Windsor
Historic Newburgh Home w/ Hudson River Views!, holiday rental in New Windsor
Historic Newburgh Home w/ Hudson River Views!, holiday rental in New Windsor

Historic Newburgh Home w/ Hudson River Views!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Lovely Loft across Madam Brett Park Entrance! Short drive to Main Street, holiday rental in New Windsor
Lovely Loft across Madam Brett Park Entrance! Short drive to Main Street, holiday rental in New Windsor
Lovely Loft across Madam Brett Park Entrance! Short drive to Main Street, holiday rental in New Windsor

Lovely Loft across Madam Brett Park Entrance! Short drive to Main Street

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Showing results 1-48 of 48
Frequently Asked Questions about New Windsor