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Chestnut Ridge Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chestnut Ridge vacation rentals

A garden with a stone wall, a wooden fence, and a gravel path.

1. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay! "
United States
Megan D.
$189 nightly
The price is $211
Nov 2 - Nov 3
Total with taxes and fees
Piermont Oasis
A wooden cabin with large windows, a wooden bench, and a view of the forest.

2. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Oct 12 - Oct 13
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

3. 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
$248 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
A house with a view of a bridge and mountains.

4. 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, (147 reviews)
"We had a great stay!!"
United States
Jasmine
$279 nightly
The price is $330
Oct 20 - Oct 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A stone pathway leading to a stone wall with a potted plant.

5. Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
$282 nightly
The price is $319
Nov 1 - Nov 2
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A wooden cabin with large windows, a wooden bench, and a view of the forest.

6. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
$279 nightly
The price is $283
Oct 12 - Oct 13
Total with taxes and fees
Harriman Outdoor Center - Cranberry Cabin
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

7. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
$732 nightly
The price is $815
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

8. 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.
$310 nightly
The price is $354
Oct 18 - Oct 19
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A stone staircase leading to a house with a stone wall and a metal gate.

9. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$372 nightly
The price is $425
Oct 12 - Oct 13
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A motel with a blue awning and a '6 Now Open' sign.

10. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (3 reviews)
"Short trip so just needed something quick, location near Westchester Airport suited us well."
United States
Anonymous traveler
$132 nightly
The price is $151
Oct 11 - Oct 12
Total with taxes and fees
1 Queen Bed | Non-Smoking
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

11. 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.
$115 nightly
The price is $135
Oct 12 - Oct 13
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Interior

12. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (52 reviews)
"One of the cleanest VRBOs I ever stayed in - it smelled so good. Very cozy and had everything we needed. The location is great!"
United States
Tara K.
$216 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
An outdoor brick oven with storage shelves, a covered table, and a welcome mat.

13. 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 traveler
$512 nightly
The price is $564
Oct 9 - Oct 10
Total with taxes and fees
Cozy Furnished Ranch! Pet friendly!
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

14. The Cozy Suite: 1BR with Free Parking

The Cozy Suite: 1BR with Free Parking
Paterson
10.0 out of 10, Exceptional, (2 reviews)
The Cozy Suite: 1BR with Free Parking
A modern hotel room with a large bed, a sofa, a TV, and a dining area.

15. 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)
$243 nightly
The price is $268
Oct 19 - Oct 20
Total with taxes and fees
Lake House King Suite near NYC/EWR/MetLife 10 min!
Two wooden chairs with bird-patterned cushions, a small round wooden table, and a vase with dried plants, all set against a wall with string lights.

16. Cozy 1-bed home, steps to NYC & MetLife. Minutes to bus and ferry. Free parking.

Cozy 1-bed home, steps to NYC & MetLife. Minutes to bus and ferry. Free parking.
North Bergen
10.0 out of 10, Exceptional, (11 reviews)
"Everything was great! Host communicated very well, listing was accurate, nice apartment. Great stay, would highly recommend!"
United States
Bennett B.
$243 nightly
The price is $281
Oct 19 - Oct 20
Total with taxes and fees
Cozy 1-bed home, steps to NYC & MetLife. Minutes to bus and ferry. Free parking.
A modern kitchen with dark cabinets, stainless steel appliances, and a dining area with a round table and grey chairs.

17. Gorgeous, 2- bedroom apartment walking distance to GWB!

Gorgeous, 2- bedroom apartment walking distance to GWB!
Fort Lee
9.8 out of 10, Exceptional, (16 reviews)
"Yes nice place"
United States
Scott b.
$340 nightly
The price is $375
Oct 11 - Oct 12
Total with taxes and fees
Gorgeous, 2- bedroom apartment walking distance to GWB!
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

18. '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, (3 reviews)
"Great stay!"
United States
Ann S.
$256 nightly
The price is $293
Oct 19 - Oct 20
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

19. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
$583 nightly
The price is $652
Oct 9 - Oct 10
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
A hot tub with a view of a lake and houses in the background.

20. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (43 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
$485 nightly
The price is $549
Nov 3 - Nov 4
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

10/10 Excellent
"The hotel was clean and quiet. The room did smell like someone had been smoking, but I don’t fault the hotel for that. Parking is available on a first-come, first-served basis, so keep in mind that the lot is small and tight. Also, the hotel only allows two people per room, which is helpful to know before booking."
Karina 1-night trip
Posted 6 hours ago
LIV Hotel Bronx - Newly Built

Find out more about Chestnut Ridge

Everything you need to know about Chestnut Ridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Ridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestnut Ridge vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chestnut Ridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $281 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestnut Ridge rentals

At Expedia, we put the best Chestnut Ridge vacation 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 vacation.

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 vacation rental in Chestnut Ridge?

Yes, we give you a choice of vacation rentals near popular attractions in Chestnut Ridge, or you can go with a more remote option if you're looking for relaxation. 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's the top vacation rental in Chestnut Ridge?

Modern Luxury Home w GameRoom & Parking: This vacation home rental outside Chestnut Ridge is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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 Buttermilk Falls Park. Sunbridge Institute and Woodbury Common Premium Outlets are a couple of places you'll find in the larger area.

What are vacation rentals like in Chestnut Ridge?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Chestnut Ridge. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.