Vacation rentals in Chestnut Ridge

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Top-rated vacation rentals in Chestnut Ridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Greenwood Lake

4.93 out of 5 average rating, 177 reviews

Lakeview Cabin at Greenwood Lake

A cozy cabin with modern amenities including new furnishings, appliances, internet, wifi, and television. Enjoy open plan living and dining room with connected full kitchen; queen bedroom; office, and a bath with walk-in shower. A large wrap-around deck with gas grill and lots of seating overlooks the lake. Parking for two vehicles. Five minutes from the Village of Greenwood Lake, 15 minutes from the Village of Warwick, and surrounded by recreation, food, shops, and more. On the NY/NJ bus line.

Jan 18 – 25

R3,854 ZAR per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep 27 – Oct 4

R2,605 ZAR per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jan 31 – Feb 7

R2,043 ZAR per night

Guest favorite

Guest suite in Pequannock Township

4.92 out of 5 average rating, 105 reviews

Comfortable & Private Guest Suite

Private home with a guest space on the 2nd story. Located in a quiet residential area with on and off street parking. Suite has a private entrance outdoor seating, personal door key code. Its a 1 bed room with a king bed , living room has a couch w/2 recliners. Access to washer & dryer in common area. Centrally located & 30 min to1 hr to major Airports, NY, Penn, NJ beaches and ski resort. Close to restaurants , shopping . Access to public transportation via bus and train is within minutes.

Jun 4 – 11

R2,286 ZAR per night

Guest favorite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 718 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

The most popular Airbnb in the area! FREE private driveway too. A few blocks to the Hudson River. Super charming, slightly quirky, private Shangri-La w/backyard chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp, though tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. E-fireplace inside. Firepit outside. Stars galore. 2 patios, yard, hammock, gardens. Read on...

Jul 1 – 8

R3,088 ZAR per night

Guest favorite

Apartment in Yonkers

4.94 out of 5 average rating, 213 reviews

Large, relaxing private 1 bedroom apartment.

Located on a quiet cul-de-sac, this self-catering 1 bedroom apartment with private driveway is located on the lower level of a private home and is perfect for anyone wishing to have a space to themselves. There is a roll-away single bed to accommodate a 3rd guest. We offer WiFi, Netflix and full cable TV access. Located near Executive Blvd and all the river towns. Plus, its only a short ride to all New York City has to offer. All reservation requests require verified Government ID.

Feb 5 – 12

R2,477 ZAR per night

Guest favorite

Apartment in Suffern

4.95 out of 5 average rating, 103 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Jun 4 – 11

R3,104 ZAR per night

Superhost

Guest suite in Dumont

4.79 out of 5 average rating, 122 reviews

Private ground level Studio Available.

This spacious and serene space has an attached garage which can fit a compact car fully, but since theres no overnight street parking, I would suggest you fit as much of your vehicle into the garage as you can in order avoid any tickets. Set the heat or AC, watch TV, nuke a meal, do some laundry, and there's a small office to gather your thoughts. There's WI-FI and your own private entrance through your garage to come and go as you please.

Oct 5 – 12

R1,453 ZAR per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Apr 18 – 25

R1,626 ZAR per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Oct 28 – Nov 4

R2,374 ZAR per night

Guest favorite

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

Our place is a private, stand-alone building separate from our house, and is cleaned thoroughly between guests including disinfecting all hard surfaces. Private cottage with full kitchen and bath in Suffern, NY. Quick walk to train & bus to NYC. Right off I-87, I-287 (NY & NJ), & NJ Rt. 17. Close to shopping & local restaurants. Off-Street parking & outdoor picnic area. NO CLEANING FEE!

May 12 – 19

R2,210 ZAR per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 207 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Oct 28 – Nov 4

R2,528 ZAR per night