Top 12 Airbnb Vacation Rentals In Westchester, New York - Updated 2024

Hannah
Hannah 
Updated
| 4 min read

Nestled between the Hudson River and the Long Island Sound, Westchester County is a peaceful and picturesque destination north of New York City. This idyllic region brims with charm, with historic homesteads dotting the countryside, calm lakes perfect for paddling, and miles of scenic hiking and biking trails. There’s something for everyone to enjoy, from art museums such as Hudson Valley MOCA to chic shopping at The Westchester. Ride rollercoasters at Playland Amusement Park for a day of family-friendly fun, or enjoy outdoor activities such as boating, horseback riding, golfing, or fishing. Explore the grand grounds of Kykuit or tour the magnificent gothic mansion of Lyndhurst, then sample craft beer at a local brewery. If you’re in search of a luxurious experience, look no further! You can take a refreshing dip in one of the Airbnbs with a pool, or indulge in some ultimate relaxation at one of the many hotels with hot tubs available. Escape the hustle and bustle of New York City, and retreat to one of these Airbnb vacation rentals in Westchester, New York.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 03, 2024.

1. Luxurious four-bedroom house in Hastings-on-Hudson (from USD 532)

Nestled in the charming village of Hastings-on-Hudson, this home is situated in Greenburgh, widely regarded as one of the best towns in Westchester County. This stunning four-bedroom house with a kitchen and a fenced backyard is perfect for your next vacation! It boasts a beautiful garden view that will leave you feeling relaxed and rejuvenated.

Stay connected with the world using the complimentary Wi-Fi and enjoy a dedicated workspace to help you stay productive during your stay. This rental also provides free driveway parking for up to four cars, so you won’t have to worry about finding a parking spot.

You will love the entertainment options available in this rental, including a 55-inch HDTV with Amazon Prime Video and Disney+. This rental is just minutes away from waterfront access, the Metro-North train station, and the historic downtown area of the village, offering plenty of opportunities for fun and exploration.

Stayed at this property?
Hastings-on-Hudson, New York, United States
12.11 km (7.6 mi) from Kensico Dam Plaza
62 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
having individual room air conditioning was a nice touch given that everybody has a different comfort threshold
the a/c was very effective in keeping the house cool and pleasant
the beds were super comfortable and the heated floors made the home cozy and warm
beds were firm but very comfortable we all got great sleep
brand new renovation incredibly clean gorgeous kitchen and high end appliances and washer dryer
Cleanliness:
very clean and spacious
extremely clean and well stocked with all necessities
most importantly it was so clean and everything in the house is new and fresh
the house was very clean and felt as if we were the first guests
the house was extremely clean and neat which is very important to me and my family
Host:
great host quick responses
the owner is very friendly and kind
he was responsive clear and kind
the host was great too we will definitely stay here again when heading down to nyc with family
the house was very nice and dan was a great host
Location:
great location for getting around
it's located in the most beautiful setting in a super quiet neighborhood
dan has a beautiful house close to the city but private and peaceful at the same time
hastings was a nice in-between location for all our activities city and country
the area the home is located is quiet with beautiful greenery and lots of walking trails
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2. Cozy one-bedroom apartment in Pleasantville (from USD 110)

This one-bedroom apartment features a comfortable queen-size bed, ensuring a good night’s sleep. The living room is equipped with an airbed, providing additional sleeping space for your family or friends. The kitchen is fully stocked and the complimentary Wi-Fi and dedicated workspace allow you to stay connected and productive during your stay. This rental also offers free on-street parking for your convenience.

This apartment is air-conditioned, ensuring that you stay cool and comfortable throughout your stay. Rockwood Hall and Rockefeller State Parks are just a 10-minute drive away, making it easy for you to explore the beautiful natural surroundings.

Stayed at this property?
Pleasantville, New York, United States
7.93 km (5.0 mi) from Kensico Dam Plaza
95 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
comfortable bed comfortable sofa
we were lucky to find amy’s apartment on airbnb
it's a quiet area and the bed was comfortable which is a big a+ for me
the kitchen was stocked with lots of necessities that made cooking easy
the bed is very comfortable as is the rest of the apartment
Cleanliness:
the apartment was very clean and modern
everything is cozy and clean and comfy
the property is absolutely clean and stylish
second time staying here - great place clean convenient and great communication with owner
sweet cozy little space :) it was super clean and comfortable
Host:
hosts are welcoming and attentive
amy and ken were great hosts
wonderful place and great host
hosts were quick to respond and we enjoyed every minute of our trip
amy was very responsive
Location:
easy walk to town and train station
such a cute space in a fantastic location
it was close to nice restaurants and close to all the main parkways
great location and great bed
the apt and the location was just perfect
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3. Studio guest suite in Ardsley (from USD 105)

This pleasant basement guest apartment in Westchester, New York, provides a comfortable stay. Inside the studio rental, there is a lounge with cozy couches, a smart television with Netflix access, a dining area, a queen-size bed, a full bathroom, and a laundry room. The suite is quiet and private, and guests have their own entrance and parking area. Up to three guests can stay here. The property is situated in Ardsley, which is a 30-minute drive from New York City.

Stayed at this property?
Ardsley, New York, United States
9.85 km (6.2 mi) from Kensico Dam Plaza
371 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 0 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
loved having the tv and couch area
well stocked keurig rack breakfast snacks and microwave popcorn were nice touches
pamela made everything to make this stay comfortable from frequent clean-ups to regular supply of coffee for breakfast
very clean many amenities a garage to park our suv plenty of room
the space itself has everything you need and pamela adds plenty of thoughtful touches to make you feel cozy
Cleanliness:
everything was clean and tidy
very nice place clean and nicely decorated
place was cozy clean and nicely furnished
the bathroom was clean and very functional
the space was clean and very calming
Host:
pamela is a great host
you’re a great host
she was so kind and helpful
owners are great and responsive
pamela was kind and responsive
Location:
the location was great as well
great house great location great time
really secure and easy entry/exit and good location
a great place to stay everything is there close to every restaurant and stores
a cute place just around 30 minutes north of the city
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4. Modern one-bedroom apartment for two guests in Pleasantville (from USD 111)

This apartment is a chic and spacious rental within a historic, Colonial house. The wonderful apartment can accommodate up to two guests and it features a sleek, modern style. Inside the apartment are a fully furnished kitchen, a living room, a dining room, a bedroom with a queen-size bed, and a bathroom with cozy in-floor heating. Guests have their own heating and cooling units, and a designated parking spot. Located in Pleasantville, the property is within walking distance of restaurants, coffee shops, and bars.

Stayed at this property?
Pleasantville, New York, United States
6.93 km (4.4 mi) from Kensico Dam Plaza
213 reviews   Wifi Available
Entire guest suite 1 Bed 3 Guests 2 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
comfortable bed spacious bathroom relaxing couch with a massive tv and even great lighting
les’s place is beautiful comfortable and has great amenities
to our further delight the refrigerator and kitchen cabinet had all the essentials
the tv appliances and closets were all bigger nicer and newer than mine
we enjoyed tivo on the 2 large screen tvs with upgraded sound systems
Cleanliness:
very clean spacious and comfortable
beautiful modern and super clean apartment
a very clean and well kept first floor apartment
very clean very neat and just what we were looking for
everything is brand new and very clean
Host:
great hosts always available for anything
les was easy to communicate with and helpful in answering our questions
les is truly a "super host"
hosts like les are an example of what the airbnb community of hosts needs to be
les is an excellent host
Location:
plus pleasantville is a wonderful place to visit
it’s a perfect location for shopping restaurants and the train
well appointed comfortable space convenient to the pleasantville train station and the pace campus
very good find in a lovely location
wonderful bed top of the line kitchen huge tv perfect location a 5 min walk from metro north
Read more reviews

5. Cottage in a private estate in Pound Ridge (from USD 225)

This cottage is cozy, quiet, and serene. The guest property consists of a scenic bedroom, one and a half bathroom, a well-equipped kitchen, and a living room that opens onto a picturesque deck. The property also has free Wi-Fi and parking on the premises. The cottage has a remote location surrounded by nature, and there’s a swimmable lake on-site. Up to two guests can stay in this nature retreat near Pound Ridge.

Stayed at this property?
Pound Ridge, New York, United States
16.52 km (10.3 mi) from Kensico Dam Plaza
168 reviews   Superhost Wifi Available
Entire cottage 1 Bed 2 Guests 1 Bedroom 1 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
the cottage was super cozy
wifi worked great and there's a landline just in case
there's complete privacy and the house is very comfortable
the bed was extreamly comfortable the grounds and view were amazing
each room has incredible views and even though it’s winter the landscape was stunning
Cleanliness:
the place is comfortable clean and quiet
really lovely and clean space
freds place was absoutely beautiful very clean lots of little conveniences
it was comfortable and clean
fred's place is clean quiet and secluded
Host:
fred was a great host
fred was a great host
fred was also very helpful throughout our stay
fred is a wonderful and helpful host
the host was super kind and we felt well taken care of
Location:
positively gorgeous location hidden away only an hour from nyc
this place is gorgeous and close to good restaurants and hiking
this location is amazing and better than any of the reviews can possibly say or describe
there are blinds on every window and they’re super easy to open and close
fred’s place is wonderful
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6. Charming apartment with a garden in White Plains (from USD 100)

An elegant style and comfortable amenities make this apartment a delightful place to stay in White Plaines. Inside the apartment, there is a sunny living room, a chic, fully equipped kitchen, two bedrooms, a full bathroom, and laundry machines. Guests can also relax in a private, picturesque garden. The apartment is situated within a historic home, but guests have a private entrance and free parking on the premises. Up to three guests can stay here.

Stayed at this property?
White Plains, New York, United States
6.29 km (4.0 mi) from Kensico Dam Plaza
32 reviews   Wifi Available
Entire guest suite 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
they even added a firepit and comfortable lawn furniture during our stay
Cleanliness:
the place so clean and comfortable felt right at home
Read more reviews

7. Scenic, hillside retreat in Croton-on-Hudson (from USD 199)

Located in the town of Croton-on-Hudson, this house overlooks the rolling foothills of the Hudson Valley. The hillside house is spacious and sophisticated, and it can accommodate up to four guests. The cabin features an airy bedroom, one and a half bathrooms, a dining room, a living area with a sleeper sofa, and a well-equipped, galley kitchen. Guests can also lounge on the screened-in patio or sit by the fire pit on the patio. The house also has Wi-Fi and free parking on the premises.

Stayed at this property?
Croton-on-Hudson, New York, United States
20.17 km (12.6 mi) from Kensico Dam Plaza
157 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
quiet private comfortable space with all the amenities
beautiful & serene cottage experience the fireplace & views were just lovely and the kitchen was well-equipped
this sleek updated carriage house is as comfortable as it gets in a beautiful setting
the great room with the fireplace is a perfect place to curl up with a book and relax
the cottage itself is nicely decorated and cozy ideal for a couple or small family
Cleanliness:
carrie's place is very clean and spacious
clean comfortable and well apportioned
carrie's house is beautiful clean and homey
house was clean and quiet
an exceptionally clean and comfortable place in a peaceful setting
Host:
the host is very responsive and accommodating
great host and will return someday
the owner(s) are very responsive and take very good care of their property
carrie is so kind and her responses were quick
amazing place and lovely hosts will absolutely stay again and again
Location:
beautiful wooded location very quiet
will definitely book this location again
serene and beautiful yet close to the town of croton
a beautiful property in a beautiful location
beautiful place to get away from the city yet so nearby
Read more reviews

8. Studio apartment for two guests in Ossining (from USD 85)

This studio apartment in Ossining provides a cozy, quiet stay. The property has accommodation for two guests and it is well-equipped with amenities. The space includes a fully stocked kitchen, a queen-size bed, and a full bathroom, as well as Wi-Fi and air conditioning. There’s also outdoor seating and free parking on the premises. Guests can enjoy hiking and bike trails nearby.

Stayed at this property?
Ossining, New York, United States
11.05 km (6.9 mi) from Kensico Dam Plaza
47 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
bed is super comfortable and kitchen very nicely equipped
Cleanliness:
beautiful stay clean absolutely comfortable
great place very clean and organized
a wonderful clean space with nice homey touches and a comfortable bed
clean and convenient place with super nice people
Host:
great host quick to respond to questions
marleny was very responsive to my questions
marlene was a great host and the place was as expected
great access to the main road in ossining a quiet stay and very friendly responsive and hospitable
Location:
the location is great and the space is cute and comfortable
very nice spot in a lovely area love that it is close to croton gorge park
very good location hosts are very responsive
we had a pleasant stay at marleny's place
we would definitely recommend marleny's place to anyone staying in the area
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9. Two-bedroom apartment for four guests in Mount Vernon (from USD 94)

This property is cheerful, compact, and cozy, and it can accommodate up to four guests. Inside the apartment is a little kitchen, two bedrooms, a full bathroom, and laundry machines. There’s also free parking on the premises. The apartment is in Mount Vernon, and it is a five-minute drive from the Metro-North train line that goes to New York City.

Stayed at this property?
Mount Vernon, New York, United States
19.84 km (12.4 mi) from Kensico Dam Plaza
247 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
he had a complimentary heater that worked really well
the space was clean and comfortable with fresh linens and other amenities that helped make my stay enjoyable
the beds were big and comfortable
mo and kizzy's apartment was wonderful
really great shower and rooms would highly recommend
Cleanliness:
clean with thoughtful touches
everything is clean and the shower is beautiful
the bathroom was spotless and had soap shampoo clean towels and toothpaste
just as pictured clean and thoughtful touches left for us
the flat itself is clean and cozy
Host:
host is very helpful
host is very helpful and answers to your questions very fast
gracious hosts would stay again
mo was a great host contacting us throughout the week to make sure everything was okay
thank you mo for hosting us
Location:
great safe location great rental a+++
great location i will stay here again next year
really enjoyed our stay at this location
parking was easy to find on the street and is close to the highway
the neighbourhood is quiet and safe
Read more reviews

10. Airy apartment overlooking Titicus Reservoir in North Salem

A sunny and cozy property, this apartment is a wonderful accommodation for couples or solo travelers. The apartment can accommodate up to two guests and it includes a fully equipped, compact kitchen, a bright living room, a dining area, a bedroom with a double bed, an elegant, full bathroom, and laundry machines. Guests have free parking on the premises, and a private entrance to the apartment. The property is located in North Salem, and it overlooks the Titicus Reservoir.

Stayed at this property?
North Salem, New York, United States
30.14 km (18.8 mi) from Kensico Dam Plaza
34 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the shower is wonderful and the pull out couch was so cool and big
super comfortable bed and lovely pressure in the shower
Cleanliness:
everything is very clean & organized
had a wonderful stay in this clean and quiet apartment
cc’s place is fantastic very clean and stylish
cc’s place is amazing everything and so clean and up to date
sparkling clean very modern and serene
Host:
hosts were very friendly and communicative
absolutely wonderful experience with a fantastic host and space
they ensured i could come in safely with my car because of the snow as caring hosts
steve and caroline are amazing hosts
Location:
beautiful location overlooking a reservoir
apartment is in a beautiful setting very close to whatever one may need
i loved the peaceful and quiet location
great place - just what you'd want for your stay - cute kitchen nice shower very comfortable bed
the location is perfect for people who want to escape from the city for a day or two
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11. Chic apartment close to the train station in White Plains

This one-bedroom apartment is stylish and brimming with amenities. The space consists of an elegant living room, a dining area, a well-equipped kitchen, a bedroom with a queen-size bed, and a full bathroom. The apartment can accommodate up to three guests and it includes access to the property’s 24-hour fitness center, business center, and scenic, rooftop terrace. Complimentary housekeeping and Wi-Fi are also included, as well as a 24-hour guest service. The property sits close to the Metro-North train line, which takes you to New York City in about 35 minutes.

Stayed at this property?
White Plains, New York, United States
4.42 km (2.8 mi) from Kensico Dam Plaza
19 reviews  
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
wifi is easy and fast
everything was great the apartment are very spacious full of light bed was comfortable
great location and amenities well appointed kitchen
Cleanliness:
furnished quarters provided a clean fully-provisioned apartment in a great building
Host:
front desk staff was cheerful and warm
ken was a great host
host was easy to communicate with and responded quickly
nice apartment - great location ideal parking friendly building staff and on-site accommodations quick responses to questions
Location:
the location was perfect
great location walking distance to the train restaurants shopping running path etc
nice quiet building but perfectly located
would recommend to anyone looking for a nice place to stay in a close-to-all walkable area
it’s a clean and stylish space and literally steps from the white plains mta station
Read more reviews

12. Barn guest house in Ossining

Enjoy a peaceful stay in this converted barn guest house in Ossining. This charming property can accommodate up to four guests, and it includes amenities such as free Wi-Fi and on-site parking. Inside the barn, there is a fully stocked kitchen, an airy room with a queen-size bed, a single bed and a sofa, a full bathroom, a laundry room, and a home gym with workout equipment. Guests can also lounge on the back patio with its comfy seating, a hammock, and a barbecue grill. The property has a quiet location near the edge of town, and it is about a 45-minute train ride into New York City.

Stayed at this property?
Ossining, New York, United States
14.06 km (8.8 mi) from Kensico Dam Plaza
99 reviews   Superhost Wifi Available
Entire cottage 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
amazing bed super fun amenities like an atari popcorn and a gym we’ll be back
the amenities including the gym and laundry room are perfect for longer stays
Cleanliness:
place was very clean and cozy
when i arrived it was super clean and cozy
place was clean and the hosts are very responsive
the barn was super cute clean and comfortable for the three of us
the barn was very clean and we had a great trip hiking and doing fall activities
Host:
tom and bonnie are great hosts very responsive and always ready to help or share info
thanks to our hosts
tom and bonnie were great hosts
tom and bonnie were very responsive to any questions i had
tom and bonnie are great hosts and have a gem of a home
Location:
great location easy communication with owners
it’s situated close to everything and quiet enough to feel like you’re on a nice stay away
we traveled up for the pumpkin blaze and it was the perfect location
wonderful private apartment that is close to ossining and sleepyhollow
a great workout space and convenient near-town location make the barn a very good spot to stay
Read more reviews

Discover the charms of Westchester County

Enjoy the scenic charms of Westchester County and have an adventure in the great outdoors of the Hudson Valley. Between the quaint towns, scenic recreation areas, and historic landmarks, there’s a lot to discover in this picturesque area north of New York City. Revel in relaxation and recreation alike! Start planning your trip today, and stay at one of these Airbnb vacation rentals in Westchester County, New York.

Stayed at this property?

Frequently asked questions about Airbnb vacation rentals n Westchester, New York


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Hannah is a freelance writer, list making aficionado, and world traveler currently based in Germany. She is an avid explorer, and believes in creating new experiences to put on her bucket list to...Read more

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