Chestnut Ridge Holiday Rentals

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Our top choices for Chestnut Ridge holiday rentals

Apartment in Bryn Mawr

JayZero
2.0 star property
The price is NZ$445
includes taxes & fees
11 Jan - 12 Jan 2026
JayZero

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is NZ$470
includes taxes & fees
11 Jan - 12 Jan 2026
Elegant Hideaway with Free Parking
9.6 out of 10, Exceptional, (4)
"Everything was great! Host communicated very well, listing was accurate, nice apartment. Great stay, would highly recommend!"
United States
Bennett B.
The price is NZ$293
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy 1-bed apartment 20 min to NYC. Easy access to bus. Great for Remote Work.
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is NZ$415
includes taxes & fees
4 Jan - 5 Jan 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is NZ$466
includes taxes & fees
11 Jan - 12 Jan 2026
Luxe 1BR Oasis - Prime NY Stay
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is NZ$398
includes taxes & fees
25 Jan - 26 Jan 2026
Forava Cabins - Tiny Cabin in the Woods
10.0 out of 10, Exceptional, (20)
"The location was perfect for our visit and the apartment was immaculately clean and well stocked."
United States
Claudia M.
The price is NZ$320
includes taxes & fees
25 Jan - 26 Jan 2026
Charming Apartment in Quiet Neighborhood
10.0 out of 10, Exceptional, (1)
"The comfort and safety "
United States
Jolena
The price is NZ$463
includes taxes & fees
19 Jan - 20 Jan 2026
Spacious 2 bedroom apartment with 1 bathroom and private street entrance
2.0 star property
The price is NZ$497
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 2-bedroom apartment - 15 mins to NYC
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is NZ$469
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$265
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is NZ$550
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is NZ$550
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC

Apartment in Bryn Mawr

Two Wash
2.0 star property
The price is NZ$636
includes taxes & fees
11 Jan - 12 Jan 2026
Two Wash
10.0 out of 10, Exceptional, (6)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is NZ$521
includes taxes & fees
4 Jan - 5 Jan 2026
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
The price is NZ$227
includes taxes & fees
28 Dec - 29 Dec
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
2.0 star property
The price is NZ$645
includes taxes & fees
5 Jan - 6 Jan 2026
Luxury 3BR Home Game Room Free Parking
2.0 star property
9.4 out of 10, Exceptional, (3)
"The apartment was nice and clean and a designated parking right at the door. The host was very helpful."
United States
Irma E.
The price is NZ$577
includes taxes & fees
4 Jan - 5 Jan 2026
2 DEEP Discounted Apts by American Dream, Sleeps 8

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is NZ$499
includes taxes & fees
16 Jan - 17 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
8.2 out of 10, Very good, (18)
"Great place great location"
United States
Daquan H.
The price is NZ$231
includes taxes & fees
8 Jan - 9 Jan 2026
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
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 Chestnut Ridge Hotel Reviews

Find out more about Chestnut Ridge

Everything you need to know about Chestnut Ridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Ridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestnut Ridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestnut Ridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestnut Ridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestnut Ridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestnut Ridge holiday rentals we have selected for you start as low as NZ$523 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestnut Ridge rentals

At Expedia, we put the best Chestnut Ridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestnut Ridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestnut Ridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestnut Ridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chestnut Ridge?

Yes, there are holiday rentals close to the most popular sights in Chestnut Ridge, or you can select a more secluded option if you're looking for a relaxing stay. Chestnut Ridge is known for its festivals and university setting. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Chestnut Ridge has to offer?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Chestnut Ridge is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Chestnut Ridge?

Explore the area and family-friendly sights such as Legoland Discovery Center Westchester, or get out into nature at a spot like Buttermilk Falls Park. Sunbridge Institute and Tice's Corner are a couple of places you'll find in the wider area.

What are holiday rentals like in Chestnut Ridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Ridge. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.