Vacation rentals in Chappaqua

4.84 out of 5 average rating, 146 reviews

A spacious great room features a large sectional sofa with decorative pillows. Natural light pours in through expansive windows that overlook the lush greenery outside. A dark coffee table is positioned in the center, complemented by a soft carpet underfoot.

Home in Ossining

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

4.94 out of 5 average rating, 136 reviews

A modern coffee station is featured on a bright countertop. A sleek Keurig coffee maker sits beside a stainless steel kettle. Two canisters, labeled 'coffee' and 'tea', are presented with wooden lids, adding a touch of warmth to the kitchen space.

Apartment in Ossining

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

4.8 out of 5 average rating, 171 reviews

A private patio area is highlighted with comfortable seating arranged around a coffee table. A barbecue grill is positioned nearby. Soft lighting is strung overhead, enhancing the cozy atmosphere. Steps lead to a landscaped area with greenery, creating an inviting outdoor space.

Apartment in Peekskill

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

4.91 out of 5 average rating, 155 reviews

A wooden bridge spans a small brook, surrounded by trees and natural vegetation. Sunlight filters through the foliage above, casting gentle illumination on the path ahead. The bridge offers a serene view of the wooded landscape, perfect for a peaceful retreat in nature.

Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

4.93 out of 5 average rating, 187 reviews

A clean bathroom is shown through an open door. It features a toilet, a shower area with white curtains, and a small cabinet mounted on the wall. Light beige tiles cover the floor, contributing to a bright and airy feel.

Apartment in Mount Kisco

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mt. Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Guest suite in Croton-on-Hudson

A spacious living area is presented with a light-colored sofa set and a wooden dining table surrounded by chairs. Large windows fill the room with natural light, complementing the neutral decor and flooring. A media unit is positioned against the wall, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 135 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

4.96 out of 5 average rating, 442 reviews

A colorful sunset is displayed over the Hudson River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the image, accentuating the serene beauty of the landscape.

Apartment in Ossining

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

4.99 out of 5 average rating, 317 reviews

A wooden serving tray displays a loaf of freshly baked bread alongside a bunch of bananas. A cup is partially visible, suggesting a beverage, while eggs rest in a pink bowl nearby. The table is made of natural wood, showcasing its unique grain patterns.

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest suite in Haverstraw

A cozy suite is presented with a spacious bed, wall-mounted lamp, and a comfortable couch. A white chair and side table are positioned nearby, while a closet is visible. Natural light enters through small windows. Stairs lead up to the main level.

4.94 out of 5 average rating, 365 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:)

4.94 out of 5 average rating, 147 reviews

An aerial view captures the rustic charm of the barn-style home, illuminated warmly by outdoor lights. Surrounding stone pathways and landscaped gardens are visible, with an inviting outdoor sitting area and grill positioned alongside the home.

Home in Mount Kisco

Incredible barn in country setting

Country setting with Vermont feel. Indoor /outdoor fireplaces with large entertainment areas. Small kitchenette, 2 BR. Pull out coach, and sleeping loft . Wifi, CAC, washer/dryer, local hiking w 3 nature preserves nearby. Major estate area. 6 min. from Mt. Kisco train station. One hour NYC. Great local restaurants. Out of the ordinary!

4.91 out of 5 average rating, 580 reviews

A spacious living area features a cozy seating arrangement with a soft white couch and a round wooden table. Sunlight filters through large windows, offering views of the lush greenery outside. A desk with a computer adds a functional workspace, complementing the rustic wooden decor.

Barn in Mount Kisco

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

4.92 out of 5 average rating, 207 reviews

A charming guest studio features a triangular roofline and a welcoming porch. Two wooden chairs are positioned on the porch, facing double glass doors that open into the interior. The surrounding area is filled with trees, creating a natural and serene atmosphere.

Guesthouse in Bedford

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

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Popular amenities for Chappaqua vacation rentals

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Wifi

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Other great vacation rentals in Chappaqua

Apartment in Croton-on-Hudson

An iron bridge arches gracefully over a rushing waterfall, with water cascading down the rocky riverbank. Lush greenery lines the scene, creating a natural backdrop. The bridge's sturdy structure contrasts with the dynamic flow of water below, offering a striking visual of nature and engineering.

4.81 out of 5 average rating, 93 reviews

Garden On The Hudson

MelanieRating, 5 stars1 week ago

Really enjoyed my stay here! The place was super clean and quiet, which I loved. It’s in a great spot—I could walk to a coffee shop, a salon, and a bunch of restaurants, which made everything super convenient. The host was also super responsive and helpful, which made the whole experience even better. Would definitely stay here again!

A view from the upper loft showcases exposed wooden beams and a stone fireplace in the main living area below. The spacious loft features a queen bed, while large windows allow natural light to fill the space. A spiral staircase connects the two levels.

Guesthouse in Bedford Hills

4.88 out of 5 average rating, 133 reviews

Barrett's Sanctuary

ReginaRating, 5 stars2 weeks ago

We were in town for a family party so the location was great. Easy to get everywhere. Beds were Clean and comfortable. Grounds were peaceful. Overall it was a lovely place to stay. I would highly recommend Stephen’s place!

4.89 out of 5 average rating, 56 reviews

A gravel fire ring is surrounded by wooden seating, including log stools and blue chairs, offering a cozy gathering space. The tiny house, painted in grey with a red door, is visible in the background, nestled among lush greenery.

Home in Ossining

Camped Inn at Sundial Farm -- Tiny House

MonicaRating, 5 stars7 months ago

Hi! The house was cute and convenient for our purposes. We were on a tight schedule so could not be there when the utilities could be explained to us which put us at an extreme disadvantage. It's a cute place to get away. Thanks for your hospitality.

A covered porch area is furnished with a light-colored sofa, two wicker chairs, and a small table. Natural light filters through large windows, illuminating the space. The flooring is painted dark, contrasting with the white walls and creating a calm and inviting atmosphere.

Guesthouse in Chappaqua

4.94 out of 5 average rating, 88 reviews

Cozy 2 Bedroom Cottage in Stunning Setting

CandiceRating, 5 stars3 weeks ago

Tamara's place was perfect for what we needed! She was very communicative and easy to work with!

5 out of 5 average rating, 7 reviews

A modern kitchen features sleek cabinetry and a spacious marble island with high-backed stools. Stylish pendant lights hang above, illuminating the space. A professional-style range and stainless steel appliances are prominently displayed, while subtle decorative elements enhance the overall design.

Home in Mount Kisco

The city escape

LoriRating, 5 stars5 days ago

All of the positive reviews are right on target. We loved our stay at this peaceful and beautiful property which truly felt like a "home away from home". The house is in great condition- was immaculate and beautifully furnished. The stunning kitchen was well-appointed. The dedicated workplace was perfect- had a closed door, beautiful view out and was a good distance from the bedrooms. Also appreciated true room darkening shades in the bedroom and a very comfy mattress. Anna and Eugene were extremely responsive and their welcoming bottle of wine was a nice touch to set the tone for our all-around 5-star experience!

4.96 out of 5 average rating, 45 reviews

The outdoor deck offers a spacious area with wooden planks, accompanied by sun chairs arranged for relaxation. A stone fire pit sits in the foreground, while a barbecue grill is positioned nearby. Lush trees frame the background, creating a serene natural setting.

Home in Greenwich

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars1 week ago

A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

4.86 out of 5 average rating, 190 reviews

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

AnalieseRating, 5 stars2 weeks ago

Our stay here in Newburgh was lovely! This place was well-stocked, very very clean, fabulously eclectic, and spectacularly spacious! We loved having two restrooms and being so close to the river and to Hudson Taco!! As the Host mentions, do carefully consider how much you care about “neighbor noise.” While I brought slippers to kindly observe the “no shoes in the house” rule, the tenants above us rudely did not. We couldn’t hear voices, but the heavy footsteps kept us awake until 1 o’clock in the morning on a weeknight and woke us up at 6:30 AM on Saturday morning. The dog scampering around or crying and whining loudly every time it was left alone in the house was also hard to bear despite our bringing ear plugs. We would 100% stay again if Sarah would kindly have us. We’re sure to have more considerate neighbors next time. Thank you for creating such a lovely space at an affordable rate.