Located 38 mi (61.1 km) from New York City, the picturesque Westchester County is a great destination to escape the hustle and bustle of the city. It sits along the Hudson River and offers verdant woodlands, beautiful historic buildings and charming towns. The most well-known attraction of the area is Kykuit a historic house built by Rockefellers which is today a museum. Another historic site to check out is Lyndhurst Mansion, also known as Jay Gould estate. For families, Legoland Discovery Center Westchester and Playland Park are must-visits. Other popular things to do include hiking, fishing, and camping in the county. Options include Rockefeller State Park Preserve, Ward Pound Ridge Reservation and Croton Gorge Park. If you are thinking of a relaxing retreat, scroll ahead for a curated list of the top luxury rentals in Westchester County, New York.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Private abode with marina views, New Rochelle (from USD 446)
From the marble floors to the stained glass windows, everything about this home suggests luxury. It also features light-filled living spaces that can easily accommodate a large group of travellers. Amenities include a TV, live-edge desk and a modern kitchen. There is also a wood-burning fireplace in the living room, allowing guests to relax and be cosy during downtime.
The rental is strategically located in Westchester County, just within the vicinity of a marina and a park. Furthermore, during their stay, guests can also enjoy easy access to Glen Island Park, Five Islands Park and several eateries.
2. Well-located home best for families, Sleepy Hollow (from USD 381)
Spacious and tastefully appointed, this Airbnb vacation rental in Westchester, New York, is perfect for a large group or family on a getaway. It is also a pet-friendly property, so your fur babies can join in on the adventure. Indoor features of the rental include central air conditioning, WiFi and high-definition TVs. With in-unit laundry facilities and a full kitchen, this place is fit even for long-term stays.
When they’re not on the back deck enjoying the views, guests can do some exploring, starting with the waterfront area found a short walk away from the property. There are also several shops, restaurants and parks in the vicinity that are worth checking out.
Top guest reviews
Amenities & Room:
the space is modern with a fabulous kitchen and spa-like bathroomsCleanliness:
the place was clean and comfortablethe house was extremely clean and the host’s communication was awesomehouse is very nice & cleanHost:
david was quick to respond and all-around great hostcourteous host easy to communicate withdavid is a thoughtful quick-responding host who wants to make sure you have a wonderful stayRead more reviewsLocation:
great place in a great locationwonderful updated property in the right locationthe location for this place was absolutely amazinggreat location convenient to the train or all major roads very close to shoppingwe enjoyed walking downtown and to the water
3. Lakewood Estate, Croton-on-Hudson (from USD 2271)
Ideal for a short-term stay in Westchester County, New York, this characterful rental farmhouse dates back to 1895. It comes with nine themed bedrooms, an elegant living room, a rustic country-inspired gourmet kitchen, a library, a formal dining room and a piano room. Spread over four levels, the villa has been furnished with care, with ample luxe features such as a fireplace, a Steinway piano, Viking and Miele appliances and smart TVs.
This rental in Westchester is surrounded by lush grounds and acres of protected woodlands. Guests will find hiking trails, tennis courts, a fire pit, a barbecue grill, and a private lake on the property. The estate is located in Croton-on-Hudson in the Hudson Valley.
Top guest reviews
Amenities & Room:
the kitchen was very well-stocked and wifi worked perfectly as did the entertainment modulesgreat place - perfect for families or large groups lots of rooms and beautiful propertythe kitchen and dining room are fantastic and allowed us to cook and eat group meals everydaya private estate with loaded facilities and a serene surrounding lakewood had a lot to offer everyonethe house is charming and the kitchen is well-equippedHost:
greta was an amazing host and there for any questions we had with quick responsesgreta was a welcoming host who was on top of answering all our questions quicklygreta was a wonderful hostgreta is a fantastic hosta fantastic property and a wonderful hostRead more reviewsLocation:
this location was really beyond perfectwhat a beautiful location away from the fraybeautiful rustic home super close to the citybeautiful house in a stunning location incredibly easy to get to from nyplenty of quiet outdoors space and a well furnished house with comfortable bedrooms and large kitchen
4. Attractive farmhouse with modern interiors, Yorktown Heights (from USD 457)
This colonial-inspired farmhouse set within lush grounds features a refined atmosphere with its beautiful design. Filled with natural light, the house offers an open-plan living room, a fully stocked kitchen and four bedrooms. Some rooms come with gorgeous handpainted murals.
The property can sleep up to eight guests. Outside, it offers a wide range of amenities including a pond, a swimming pool, a gazebo and a large patio. The rental is located in Yorktown Heights.
Top guest reviews
Amenities & Room:
there were also fresh flowers in every roombut our favorite spot was the wonderful heated poolwe had an issue with the water heater and dani was very quick to help resolve the problemthe evenings we are watching movies and our morning breakfasts are amazing with the flat top griddlethe house is so spacious we really had room to spread out and relaxCleanliness:
the house was clean spacious and well maintainedthe house is spacious and extremely cleanrooms are comfortable and place is very cleanthe pool was lovely and clean surrounded by trees and nature (we spotted deer )Host:
wonderful place and great hostdani was such a gracious hostdani is very responsive in answering questions and troubleshootingdani was a very responsive hostdani was an excellent host for our familyRead more reviewsLocation:
the house is beautiful and is in a great locationdani’s place is in a perfect location secluded in the woods with lots of privacythe yard was fun and we were in a great location to explore nearby attractionsthe house pool and location are perfect for those looking for a little r and rthis house is definitely the perfect place to stay in yorktown heights
5. Impressive country house with extensive grounds, North Salem (from USD 1500)
Hidden away on a hilltop, this country manor-style property provides guests with four bedrooms, a living room, a dining room and a full kitchen. It has been fitted with high-end amenities such as a Viking range and Sub-zero refrigerator in the kitchen and a fireplace in the living room.
The property’s outdoor features are outstanding. It offers over 18 acres (7.3 hectares) of grounds that look onto the Taconic Mountains. A pool, a gazebo, a front yard and a backyard are its major features.
Top guest reviews
Read more reviewsHost:
the owners were so accessible and helpfullastly great owners who were extremely responsivethe owners are very gracious and accommodating
6. Westchester County Castle, Ossining (from USD 933)
This house in Westchester County is beautifully furnished combining traditional elegance with modern comforts. The mansion offers five bedrooms that can sleep up to twelve guests. A beautifully appointed sunken living room, full of natural light, comes with a smart TV, a billiards table and a fireplace. The kitchen is fully equipped with state-of-the-art appliances. A separate sitting room with a work desk is available as well.
The highlight of the rental is its “Sky Lounge” found on the topmost level and featuring a wet bar, a media room and skylights.
Top guest reviews
Amenities & Room:
beautiful house with lots of great rooms for gatheringRead more reviewsHost:
the property manager was super helpful -- would highly recommend
7. Welcoming house overlooking Hudson River, Ossining
Enjoy a soothing nature retreat with this tastefully-furnished mid-century house in Ossining that offers incredible views of the Hudson River. The two-level house includes an open-concept living area with dining facilities, a fully equipped kitchen, an entertainment room, a back room with a desk and three bedrooms.
The house can host up to six guests. A wrap-around deck on the main level promises sweeping views of the river and surrounding woods. The lower level additionally comes with its own deck. A mature garden surrounding the house adds to its charm.
Ossining, New York, United StatesSuperhost
Accommodates: 6
Top guest reviews
Host:
the hosts are so easily approachableand the hosts have lots of useful tips for the areaplus the hosts are the nicest and most helpful peopledagny and michael were great hosts for our family weekend stayRead more reviewsLocation:
many cool things to do close bygreat location for exploring the hudsonit’s close to tarrytown and easy to get to sleepy hollow and even nyc
8. Large family house with pool, West Harrison
This house located close to The Westchester mall is a welcoming option surrounded by landscaped grounds.
The property offers four bedrooms, a living room with a fireplace, a well-furnished family room with a wet bar and a fireplace, and a fully functional eat-in kitchen. The outdoor amenities include a pool and a front patio.
Accommodates: 10
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
9. Traditional manor-style estate, Mount Kisco
Located in Bedford Corners around 1 mile (1.6 kilometres) from downtown Mount Kisco, this property located on sprawling grounds provides a country manor feel. Featuring traditional-style luxury furnishings, the estate includes eight bedrooms, two living rooms, a capacious open-plan living area, a fully equipped kitchen, a formal dining room, a well-equipped gym and a billiards room, spread over three floors.
The house at the maximum can hold up to 16 guests. The outdoor amenities include a front porch, swimming pool, tennis courts, a viewing area, and landscaped gardens. The house features loads of high-end amenities including a Viking gas range, Cuisinart cookware, 4K smart TVs, an Eero mesh WiFi system and a TOTO Japanese toilet.
Mount Kisco, New York, United StatesAccommodates: 16
Top guest reviews
Amenities & Room:
the beds were all comfortable and the amenities and grounds were outstandingthe beds are comfortable the space is even larger than the photos make it out to bewe had a private chef and he said that the kitchen was a pleasure to work inthe house and surrounding grounds are extremely well maintained with extensive landscaping and beautiful stone patio and pool areawe also loved the dining room which was able to fit the whole group for dinnerCleanliness:
very clean and spaciousvery clean well maintained hosts are accommodating and great for large groupsthe spaciousness for our large team clean environment and beautiful landscaping will have us returning for future eventsHost:
the property manager was very responsive to any requests during our stayjoan is a great hostfantastic house with an outstanding hostand joan was a fabulous hostadditionally the host has made communication incredibly easy and continuously accommodated and assisted us with our needsRead more reviewsLocation:
perfect place to stay
10. Katonah Station House, Ossining
An erstwhile inn, this graceful country house is located in Ossining. Surrounded by verdant grounds, the rental provides a serene setting. The property offers eight bedrooms and can comfortably accommodate up to fourteen guests. The interiors feature traditional decor with touches of luxury. Some of its luxe features include a Viking gas range, TVs, fast WiFI and a fireplace.
In terms of its outdoor features, the rental offers a fire pit and a large patio.
Ossining, New York, United StatesAccommodates: 14
Top guest reviews
Amenities & Room:
everyone was comfortable and had there own space enough bathrooms and lots of comfortable communal spaces to usethe kitchen and dining area were great beautiful patio and grounds for relaxinggreat communal and outdoor space and plenty of lovely bedrooms and bathroomsthe dining room table fit us all and the kitchen is well stocked with everything you needit's an amazing house to cook a group meal with a fully stocked kitchenCleanliness:
the house is clean and cozythe house is very cleanvery clean and nice homethe house was super clean and had all we needed to be comfortable for the weekalex's home is a beautiful spacious clean and fun place to stayHost:
host provided everything we needed for a wonderful fall stayfantastic experience gracious hosts and lovely homewonderful hosts that are very happy to accommodate your groups needsalex couldn’t have been a more gracious hostthis is a great place with a great hostRead more reviewsLocation:
easy distance to walking paths and hikes easy distance to the metro northlocated conveniently close to metro north it’s the perfect house for a gathering in the countrythis was a great location for a group gatheringthe property is extraordinary lush and beautifully groomed - a perfect place to wander or just chill outit is a perfect place for large groups
11. Stunning lakeside retreat, Pound Ridge (from USD 1200)
Featured in architectural magazines, this spectacular lakeside mansion is sure to leave you amazed with its amenity-laden, contemporary-style interiors. Located in Pound Ridge, the property sits on a secluded estate set by the shore of a natural lake surrounded by a forest reserve. The property boasts an open floor plan that comes with 18 ft (5.5 m) ceilings and walls lined with windows, flooding the house with natural light.
It encompasses an expansive living room, a gourmet kitchen and five bedrooms that can sleep up to ten persons. Its amenities include a private dock, an indoor heated swimming pool, a hot tub, four decks and children’s play facilities such as a trampoline. Other features include Bosch appliances, hardwood floors and an outdoor fire pit.
Top guest reviews
Amenities & Room:
the pool area is amazing and the outdoor space is fantasticblack out windows in every room were also a nice touchclean well stocked beautifully appointed and all of the amenities you could want (comfortable beds too )Cleanliness:
everything is in great condition and feels clean and safeRead more reviewsHost:
jonathan was truly a super hostjonathan and polina were wonderful hostsjonathan was a wonderful host--thoughtful and responsivecannot recommend this property more highly thanks to jonathan and his family for hosting usjon was quickly responsive to inquiries and very easy to deal with
Relax and recharge yourself in Westchester
Eager to spend a few days amid tranquillity and complete comfort? We have found you the top luxury rentals in Westchester, New York, that you can use to plan out the perfect vacation amid gorgeous surroundings.
Frequently asked questions about luxury rentals in Westchester County
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