Vacation rentals in Chappaqua

5 out of 5 average rating, 119 reviews

Home in Greenwood Lake

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

TatyanaRating, 5 stars1 month ago

We had a staycation here and it was absolutely lovely. We enjoyed the space, especially the view. The hot tub was great in the chilly nights, played in the game room a bit, cooked in the kitchen and enjoyed some meals in the dining room. Easy to find, but felt very private. Thank you for sharing the lovely place.

4.92 out of 5 average rating, 26 reviews

A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

Light-filled Beach House Steps from the Sand

FayeRating, 5 stars20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

4.85 out of 5 average rating, 133 reviews

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

Clarissa's Paradise

JamalRating, 5 stars2 months ago

First of all I would like to thank Carmen for letting me stay at her beautiful home. I enjoyed the time I spent at the air bnb even though it was a very busy weekend for me. Carmen home was clean and comfortable, also a very convenient location close to so many places. The home is also pretty spacious I was able to have a nice family dinner and gathering there. I would definitely recommend staying at this beautiful air bnb, Carmen was a great host Thankyou again.

5 out of 5 average rating, 43 reviews

A wooden boardwalk leads toward the beach and ocean, bordered by vibrant umbrellas and beachgoers enjoying the sun. The clear blue sky reflects over the water, creating a serene coastal view. The structure allows for easy access to sandy shores.

Home in Ocean Beach

Sunny Spacious Pet Friendly Steps from the Beach

LoriRating, 5 stars6 months ago

Excellent stay! Hosts were responsive and very helpful. The house is absolutely beautiful, the pictures do not do it justice. The location is perfect and we had a wonderful time. The house was very clean and had beautiful decor. Highly recommend! Five stars one of my favorite and I will definitely be back. Thank you to Susan and Zoe for a wonderful stay.

5 out of 5 average rating, 38 reviews

Home in New Paltz

Luxury Home with Mountain Views

GiladRating, 5 stars2 months ago

The house is even more beautiful than the pictures. It is beautifully designed and extremely clean and comfortable. Kitchen is well equipped, beds are very comfortable, and the playroom for the toddlers was an amazing addition to the experience. Judy was very responsive and considerate of all of our needs. We would love to come back for another stay!

4.98 out of 5 average rating, 64 reviews

A screened-in porch is showcased with a well-maintained hot tub and two wooden Adirondack chairs. Surrounding greenery is visible through the screens, creating a serene and private atmosphere.

Home in New Paltz

Spacious, Quiet 4 Bedroom + All Season Hot Tub

KatherineRating, 5 stars3 days ago

My family had a fabulous 4 night stay at Tina’s place! There was plenty of space to lounge around and we all enjoyed the hot tub. We were a short drive to so many restaurants, farms, breweries and hiking spots. Tina responded immediately every time we asked a question. Would definitely stay here again!

4.99 out of 5 average rating, 174 reviews

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

Incredible Long Beach Private Rental

AllanRating, 5 stars3 months ago

Absolutely superb hosts and such a great location. Steven couldn’t have been a better host, our kids and us loved his place and would highly recommend. Thoughtful touches everywhere and very clean. Hope we can stay again sometime.

4.96 out of 5 average rating, 53 reviews

A waterfront area features two blue Adirondack chairs set on green grass, accompanied by a stone fire pit. The lake extends into the distance, framed by rolling mountains under a clear blue sky. A decorative swan enhances the tranquil outdoor setting.

Home in Greenwood Lake

Water's Edge Lakefront Home

KaylaRating, 5 stars4 months ago

WOW!! We cannot say enough amazing things about our stay. We stayed for the holidays and the snow surrounding the lake was the most beautiful surrounding imaginable. It was so peaceful and we watched both sunrises and sunsets there. Plus there were tons of beautiful swans to appreciate! The house was extremely pristine, decorated beautifully for the holidays, and felt like home. This was such a special stay and our host was so accommodating! We will absolutely be back.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chappaqua vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chappaqua's top sights

Jacob Burns Film Center33 locals recommend

Village Social Kitchen & Bar17 locals recommend

Jacob Burns Media Arts Lab11 locals recommend

Starbucks10 locals recommend

Jean-Jacques' Culinary Creations10 locals recommend

The Black Cow Coffee Company9 locals recommend

Other great vacation rentals in Chappaqua

Apartment in Downtown Stamford

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

4.94 out of 5 average rating, 141 reviews

Apartment in Wallkill

Log Cabin Apartment Great for Outdoor Enthusiasts

MichaelRating, 5 stars3 months ago

We loved our time at this beautiful cottage! We have been to lots of Airbnb’s, and most have been a good experience. This cottage was something more. We both felt instantly relaxed when we walked in the door. It was so cozy and comfortable. We slept great in the comfy bed. The pictures can’t describe the feeling of the place. Warm, cozy, peaceful, inspiring, comfortable, quiet and truly rejuvenating. I will be making a trip to the area again as soon as possible, just to stay in this cabin retreat.

4.84 out of 5 average rating, 32 reviews

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Gray cabinetry contrasts with a mosaic backsplash. A sink is positioned beneath a window, while a clean mat lies on the floor near the countertop.

Apartment in Brentwood

Home away your home

GeraldineRating, 5 starstoday

Nice place exactly what the pictures show .. Super nice host.. but if you are looking for a quiet place. This place is definitely not it. You can hear every move and every sound from the people that live upstairs last night we spent a good few hours hearing a baby cry. Also they have the children’s toys such as a trampoline up against the window of the unityou do park on the street and the owner or tenants whoever lives upstairs parks in the driveways. it’s a very tight walk in between cars in the driveway because they do park a lot of cars in the driveway side-by-side.

4.91 out of 5 average rating, 33 reviews

A two-story house is set on a sloping waterfront, surrounded by trees. The exterior features large decks on both floors, with seating and umbrellas visible. A dock extends into the water with additional seating, and a sandy area is positioned nearby.

Home in Vernon Township

Highland Bluffs Lake House, 50 miles from NYC

JessicaRating, 5 stars2 months ago

Our family loved this spot! The house is beautiful, clean and very peaceful. My kids all loved the basement which had a great assortment of games, toys and books. We visited for a weekend and went snowtubing at Mountain Creek (only about 12 minutes away). We also really enjoyed nearby Warwick, NY where we found nice shops and restaurants. It was a great stay - highly recommend!

4.96 out of 5 average rating, 73 reviews

An open living area is presented with a spiral staircase leading to an upper level. A dining table with dark placemats and a vase of fresh flowers is centrally located. Cozy seating options include a textured sofa and an accent chair, while a television is mounted on the wall.

Condo in Vernon Township

Peaceful Mountain Retreat

Adam Rating, 5 stars1 week ago

Perfect stay. Felt at home from the moment I arrived and Adam was really easy to communicate with and very accommodating. The condo was clean and cozy. For sure will be back.

5 out of 5 average rating, 11 reviews

A screened-in veranda features wooden flooring and white railings, overlooking a lush green yard. Soft outdoor lighting is strung along the ceiling. Views of trees and distant mountains extend beyond the space, creating a sense of tranquility.

Villa in New Paltz

Country House, Mountain Views, Dine, Bike, & Hike

AriellaRating, 5 stars3 months ago

Absolutely beautiful home! Carl and Rebecca were wonderful hosts - they were super responsive and accommodating. And their home is lovely down to all the little details, from the soft bathrobes to the warm spaces to hang out in. We had a wonderful stay at their home and would love to come back!

4.92 out of 5 average rating, 119 reviews

A designated outdoor seating area features four wooden Adirondack chairs arranged around a stone fire pit. Lush green trees and shrubs create a natural backdrop, while a paver stone pathway invites relaxation and conversation in a serene setting.

Condo in Vernon Township

Perfect Retreat! Ski in/out, hot tub, bike races.

BruceRating, 5 stars1 month ago

A great weekend ski retreat. Easy access to the unit and close to the elevator. Great little kitchen, with toaster and k-cups. Very large bathroom. Host gave clear instructions with codes for all amenities. The heated pool and outdoor sauna were a big hit. Host allows late check out for a fee which was very convenient for us.