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Chestnut Ridge Holiday Rentals

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Our top choices for Chestnut Ridge holiday rentals

1. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is NZ$345
includes taxes & fees
7 Sept - 8 Sept
Piermont Oasis

2. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is NZ$374
includes taxes & fees
30 Aug - 31 Aug
Harriman Outdoor Center - Mountain Laurel Cabin

3. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is NZ$491
includes taxes & fees
24 Aug - 25 Aug
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

4. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is NZ$226
includes taxes & fees
24 Aug - 25 Aug
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

5. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is NZ$462
includes taxes & fees
31 Aug - 1 Sept
Harriman Outdoor Center - Cranberry Cabin

6. The Comfy Suite: 1BR with Free Parking

The Comfy Suite: 1BR with Free Parking
Paterson
10.0 out of 10, Exceptional, (1 review)
"Amazing location very clean quiet very comfortable. Im gonna stay everytime in come to town."
United States
Dollar Bill H.
The price is NZ$485
includes taxes & fees
24 Aug - 25 Aug
The Comfy Suite: 1BR with Free Parking

7. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is NZ$604
includes taxes & fees
2 Sept - 3 Sept
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

8. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"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$686
includes taxes & fees
24 Aug - 25 Aug
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

9. Cozy Furnished Ranch! Pet friendly!

Cozy Furnished Ranch! Pet friendly!
Fair Lawn
9.8 out of 10, Exceptional, (9 reviews)
"Charlie was great house was very clean well kept and had all the amenities you can think of place with dog friendly and had a huge backyard that we were allowed to let our dogs roam. This is a hidden gem in Fairlawn, New Jersey. "
United States
Anonymous traveller
The price is NZ$906
includes taxes & fees
1 Sept - 2 Sept
Cozy Furnished Ranch! Pet friendly!

10. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (20 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is NZ$261
includes taxes & fees
31 Aug - 1 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

11. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is NZ$549
includes taxes & fees
24 Aug - 25 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

12. Lake House King Suite near NYC/EWR/MetLife 10 min!

Lake House King Suite near NYC/EWR/MetLife 10 min!
Passaic
10.0 out of 10, Exceptional, (1 review)
The price is NZ$438
includes taxes & fees
24 Aug - 25 Aug
Lake House King Suite near NYC/EWR/MetLife 10 min!

13. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is NZ$864
includes taxes & fees
30 Aug - 31 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake

14. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
The price is NZ$524
includes taxes & fees
24 Aug - 25 Aug
Villa Verde B&B, bsm, Greenwood Lake NY

15. Home away from home

Home away from home
Dumont
9.0 out of 10, Wonderful, (7 reviews)
"Jennifer was amazing! She accommodated us even with our very last minute request. The place was spotless and Jennifer was so helpful. Just an awesome experience! I will definitely book it again!"
United States
Elisa G.
The price is NZ$851
includes taxes & fees
24 Aug - 25 Aug
Home away from home

16. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$360
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom retreat minutes from West Point!

17. Spacious 900 sf 2-bedroom, private street entrance, near GW Bridge

Spacious 900 sf 2-bedroom, private street entrance, near GW Bridge
Paterson
6.0 out of 10, (2 reviews)
"The comfort and safety "
United States
Jolena
The price is NZ$405
includes taxes & fees
9 Sept - 10 Sept
Spacious 900 sf 2-bedroom, private street entrance, near GW Bridge

18. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is NZ$680
includes taxes & fees
24 Aug - 25 Aug
Luxury NYC Home Game Room Free Parking

19. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is NZ$670
includes taxes & fees
24 Aug - 25 Aug
Spacious 3BR Luxe Escape near NYC

20. NY City Views Retreat & Good Transportation

NY City Views Retreat & Good Transportation
Guttenberg
9.6 out of 10, Exceptional, (4 reviews)
"My family enjoyed our stay. The home was immaculate and looked even better in person than in the pictures. Will definitely stay again in the future."
United States
Kevin W.
The price is NZ$302
includes taxes & fees
25 Aug - 26 Aug
NY City Views Retreat & Good Transportation
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chestnut Ridge holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chestnut Ridge. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chestnut Ridge. Seeing all the best attractions is bound to make you fall in love with Chestnut Ridge. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chestnut Ridge short-term rentals, that won’t be hard to do.

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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Chestnut Ridge is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

What can I see and do in Chestnut Ridge?

Explore the area and family-friendly sights such as Rockland Bakery, or get out into nature at a spot like Rockland Lake State Park. Sunbridge Institute and Woodbury Common Premium Outlets 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.