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Compare 330 Vacation Homes in Chestnut Ridge with updated reviews, rates, and availability.

NYC Paradise near metro with 3 baths - parking - laundry

9.6 out of 10, Exceptional, (26)
"We visited NY for the Subway Series game at Yankee Stadium. I chose this home for its closeness to the stadium and set up. There were a couple of issues with home upon arrival, but nothing that hampered our stay. Parking is hit or miss. "
The price is AED 937
AED 2,641 total
includes taxes & fees
7 Mar - 8 Mar
NYC Paradise near metro with 3 baths - parking - laundry

Cozy and beautiful house

10.0 out of 10, Exceptional, (20)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

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

10.0 out of 10, Exceptional, (32)
"Hot tub was awesome. Near bear mountain, also relatively easy train access to NYC across bridges."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Not your average Basement , 30 mins from Time Square, NYC

9.2 out of 10, Wonderful, (12)
"My girlfriend and I were very happy with our stay here. Valentine was very helpful and easy to get in touch with if we had any questions or needed anything. The basement was extremely cozy, comfortable, clean, and had everything we needed for our getaway. We were very happy with the accommodations and also very happy with the location. Pharmacies, restaurants, and convenience stores were all within walking distance. Would definitely recommend!"
Not your average Basement , 30 mins from Time Square, NYC

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

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

9.6 out of 10, Exceptional, (49)
"We stayed here with our 3 dogs between Christmas and New Years. It is in a gorgeous neighborhood of sprawling estate homes. This property had tons of room to spread out. The yard is HIGE and completely fenced in. The rooms are decorated with the photography work of the owner and other interesting pieces. Plenty to do on site and not too far from the city. Lisa was great and even let our dogs out to potty so we could relax traveling into the city for a show and dinner. We would love to...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

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

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Large Family House On The Lake

9.6 out of 10, Exceptional, (56)
"It was perfect for us. We have stayed 7 guys and had a lot of fun. "
Large Family House On The Lake

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

2.0 star property
8.8 out of 10, Excellent, (5)
"This home was well kept , it was a little inconvenient with the small full beds , appreciated the location and how to be with family. "
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is AED 918
AED 1,359 total
includes taxes & fees
10 Mar - 11 Mar
Contemporary Cozy Cottage

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.2 out of 10, Wonderful, (5)
"Great location, quite dead end. Excellent value, we had a very comfortable stay.Walking distance to the station for Metro North into NYC. Great deli just around the corner. Responsive hosts, will gladly use again!! "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Modern Castle-like 3bd/2ba/den, close to NYC!

10.0 out of 10, Exceptional, (30)
"This was the perfect spot for my family. Plenty of space and toddler/kid friendly. 20 minutes from American dream mall and close to NYC. "
Modern Castle-like 3bd/2ba/den, close to NYC!

3 Bedroom apartment close to ny city, parking, tv in bed rooms and living

2.0 star property
3 Bedroom apartment close to ny city, parking, tv in bed rooms and living

Charming 3-bedroom house with AC, WiFi in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118

9.8 out of 10, Exceptional, (117)
"My partner and I stayed here for a quiet weekend getaway and it was perfect. The home was cozy and welcoming. Enjoyed the snow fall and picturesque view of the frozen lake. Would definitely book again."
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118

Up-to-date Home w/ Pool, Playground & Fireplace!

10.0 out of 10, Exceptional, (1)
Up-to-date Home w/ Pool, Playground & Fireplace!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

2 BEDROOM 3RD FLOOR RENOVATED W/KITCHEN - 3 MINUTES TO SUBWAY

9.4 out of 10, Exceptional, (42)
"We recommend because …1. Location 2. Cleanliness 3. Never heard the neighbours 4. Big place for NYC 5. Affordable : good value for money —-The not so good : got the wrong code to get in & it took 30 min to solve with the help of VRBO . Double check the day before you arrive . It says it was renovated but not the bathroom! Windows don’t shut properly: bring earplugs . We asked for extra blankets as they have the weirdest and noisiest heating system: over heats in the morning and especially...
2 BEDROOM 3RD FLOOR RENOVATED W/KITCHEN - 3 MINUTES TO SUBWAY

SPACIOUS AND OPEN PROPERTY W/KITCHEN - 3 MINUTES TO SUBWAY

8.6 out of 10, Excellent, (38)
"The suite was very clean. Although the heater broke on one of the days of our stay it was fixed rapidly. Very close to the subway and deli and restaurants etc. "
SPACIOUS AND OPEN PROPERTY W/KITCHEN - 3 MINUTES TO SUBWAY
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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Other property types in Chestnut Ridge

Global Luxury Suites at The Arches

2.5 star property
6.8 out of 10, (398)
"I was told that I would receive water...there was none..online shows that there is kitchenette..it was not a full kitchen no cutting knife etc. There was wifi but it a the basic..no access to streaming cites. Great furniture and setting."
The price is AED 378
AED 780 total
includes taxes & fees
11 Mar - 12 Mar
Global Luxury Suites at The Arches

Kitchenette in private original brownstone building

6.2 out of 10, (15)
"I was most concerned when I saw reviews about lack of communication with the owner and a confusing check in process, because I've had a few negative experiences with that. Please be assured that the check in process was clear and smooth. The building is historic and has been through some things over the years, and it shows on the interior. However, the room is fully renovated and so clean, with some original details lovingly preserved. The room I had was much larger than the photos made it...
The price is AED 331
AED 588 total
includes taxes & fees
9 Mar - 10 Mar
Kitchenette in private original brownstone building

Great Looking Studio apartment in NYC Brownstone

9.0 out of 10, Wonderful, (11)
"I recently had the pleasure of staying at this exceptional VRBO property in the heart of Harlem, and it truly exceeded all expectations! I was born and raised in Harlem and the place felt like home, I would definitely stay here again on future trips.The charm of the original 1900s brownstone is breathtaking, with its high ceilings, intricate pocket doors, and a stunning gold statue that greets you upon entry, setting the tone for a unique and memorable experience. The location is unbeatable—just...
The price is AED 639
AED 937 total
includes taxes & fees
7 Mar - 8 Mar
Great Looking Studio apartment in NYC Brownstone
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.