Book Holiday Homes in Pound Ridge

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Featured Holiday Homes in Pound Ridge

Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge NY
Stay at this family-friendly holiday home in Pound Ridge. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Pound Ridge Town Park and Ridgefield ...
Opens in a new windowOver Sized Colonial on Private Road.
beautiful contemporary house , only one hour from Manhattan

beautiful contemporary house , only one hour from Manhattan

Pound Ridge NY
Stay at this holiday home in Pound Ridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pound Ridge Town Park and Hemingway Property ...
Opens in a new windowbeautiful contemporary house , only one hour from Manhattan
RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !

RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !

Pound Ridge NY
Stay at this family-friendly holiday home in Pound Ridge. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Pound Ridge Town Park and Keeler ...
Opens in a new windowRAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
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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.

Pound 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 Pound Ridge vacation homes are the perfect way for you to wing it.

Holiday houses in Pound 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 Pound 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 Pound Ridge adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pound 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 Pound 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.

Pound Ridge Holiday Homes essential information

Accommodation
361 Holiday Homes
Lowest Price
NZ$213
Highest Price
NZ$355
Popular accommodation
Over Sized Colonial on Private Road. , beautiful contemporary house , only one hour from Manhattan, RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !

Top trending hotels in Pound Ridge

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 NZ$244 per night from 5 Jan to 6 Jan
NZ$244
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowBaymont by Wyndham White Plains - Elmsford
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 21 Dec to 22 Dec
NZ$213
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly hotel in Norwalk. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowEVEN Hotel Norwalk by IHG
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is NZ$355 per night from 8 Jan to 9 Jan
NZ$355
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in White Plains. Enjoy free Wi-Fi, breakfast (surcharge) and free airport pick-up. Our guests praise the bar and the helpful ...
Opens in a new windowSonesta White Plains Downtown
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Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
The price is NZ$245 per night from 4 Jan to 5 Jan
NZ$245
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowHampton Inn White Plains/Tarrytown
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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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^Subject to availability and chosen travel dates.