Book Holiday Homes in Chestnut Ridge

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chestnut Ridge

Spacious Harlem Brownstone Garden 2-Bedroom Apartment with a large rear yard,

Spacious Harlem Brownstone Garden 2-Bedroom Apartment with a large rear yard,

New York
With a stay at this vacation home in New York (Manhattan), you'll be within a 5-minute drive of Columbia University and Central Park.
Spacious Harlem Brownstone Garden 2-Bedroom Apartment with a large rear yard,
Great Looking Studio apartment in NYC Brownstone

Great Looking Studio apartment in NYC Brownstone

New York
The price is AU$337 per night from 19 May to 20 May
AU$337
includes taxes & fees
19 May - 20 May
With a stay at this vacation home in New York (Manhattan), you'll be within a 5-minute drive of Columbia University and Central Park.
Great Looking Studio apartment in NYC Brownstone
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Stony Point
Located in Stony Point, this vacation home is within a 15-minute drive of Bear Mountain State Park and United States Military Academy.
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Save an average of 15% on thousands of hotels when you're signed in
NYC Paradise near metro with 3 baths - parking - laundry

NYC Paradise near metro with 3 baths - parking - laundry

The Bronx
The price is AU$1,284 per night from 25 Apr to 26 Apr
AU$1,284
includes taxes & fees
25 Apr - 26 Apr
With a stay at this vacation home in Bronx, you'll be within a 5-minute drive of Yankee Stadium and Central Park.
NYC Paradise near metro with 3 baths - parking - laundry
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Yonkers
With a stay at this vacation home in Yonkers (Northeast Yonkers), you'll be within a 10-minute drive of Sarah Lawrence College and NewYork-Presbyterian Westchester ...
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Greenwood Lake
Located in Greenwood Lake, this vacation home is within a 5-minute drive of Greenwood Lake and Lion's Field Park.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Hastings-on-Hudson
With a stay at this vacation home, you'll be centrally located in Yonkers, within a 15-minute drive of Fordham University and New York Presbyterian ...
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Luxury 3Bed Private Apartment Near Manhattan

Luxury 3Bed Private Apartment Near Manhattan

New Rochelle
The price is AU$960 per night from 25 Apr to 26 Apr
AU$960
includes taxes & fees
25 Apr - 26 Apr
Located in New Rochelle, this vacation home is within a 15-minute drive of Bronx Zoo and Fordham University.
Luxury 3Bed Private Apartment Near Manhattan
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2 out of 5
Monroe
Located in Monroe, this vacation home is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Don't see what you're looking for?
See all available properties in Chestnut Ridge
View all properties
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.

Chestnut Ridge Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chestnut Ridge vacation homes are the perfect way for you to wing it.

Holiday houses in Chestnut Ridge let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chestnut Ridge in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chestnut Ridge adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chestnut Ridge with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chestnut Ridge vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chestnut Ridge Holiday Homes essential information

Accommodation
324 Holiday Homes
Lowest Price
AU$202
Highest Price
AU$1,284
Popular accommodation
Spacious Harlem Brownstone Garden 2-Bedroom Apartment with a large rear yard,, Great Looking Studio apartment in NYC Brownstone, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, NYC Paradise near metro with 3 baths - parking - laundry, PureHeart House, Spacious, Peaceful 3bdr House in Yonkers, BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view., Modern 4BD/3BA w/Parking & deck & 29 min>NYC, Luxury 3Bed Private Apartment Near Manhattan, Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Top trending hotels in Chestnut Ridge

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

3 out of 5
2167 Route 4 East, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 1 May to 2 May
AU$272
includes taxes & fees
1 May - 2 May
A stay at Hyatt Place Fort Lee / George Washington Bridge places you in the heart of Fort Lee, within a 10-minute drive of Central Park and American Dream.
Hyatt Place Fort Lee / George Washington Bridge
The Park Hotel at Meadowlands

The Park Hotel at Meadowlands

3.5 out of 5
2 Meadowlands Plaza, East Rutherford, NJ
Fully refundableReserve now, pay when you stay
The price is AU$275 per night from 30 Apr to 1 May
AU$275
includes taxes & fees
30 Apr - 1 May
A stay at The Park Hotel at Meadowlands places you in the heart of East Rutherford, within a 5-minute drive of American Dream and MetLife Stadium.
The Park Hotel at Meadowlands
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 27 Apr to 28 Apr
AU$250
includes taxes & fees
27 Apr - 28 Apr
With a stay at Baymont by Wyndham White Plains - Elmsford in Elmsford, you'll be in the historical district, just a 1-minute walk from Captain Lawrence Brewing ...
Baymont by Wyndham White Plains - Elmsford
Save an average of 15% on thousands of hotels when you're signed in
Hotel MOCA NYC

Hotel MOCA NYC

2 out of 5
505 W 181st St, New York, NY
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 30 Apr to 1 May
AU$202
includes taxes & fees
30 Apr - 1 May
With a stay at Hotel MOCA NYC in New York (Manhattan), you'll be within a 5-minute drive of Yankee Stadium and Columbia University.
Hotel MOCA NYC
Don't see what you're looking for?
See all available properties in Chestnut Ridge
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.