Holiday rentals in Chappaqua

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Top-rated holiday rentals in Chappaqua

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Guest favourite

Flat in Ossining

4.94 out of 5 average rating, 136 reviews

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

Guest favourite

Home in Yorktown Heights

4.91 out of 5 average rating, 155 reviews

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.

Guest favourite

Flat in Mount Kisco

4.93 out of 5 average rating, 187 reviews

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.

Top guest favourite

Guest suite in Croton-on-Hudson

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.

Top guest favourite

Flat in Ossining

4.96 out of 5 average rating, 442 reviews

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.

Superhost

Flat in Newburgh

4.86 out of 5 average rating, 190 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Superhost

Home in Chappaqua

4.87 out of 5 average rating, 78 reviews

Chic and Cozy 2BD 1920's Cottage Retreat

Welcome to the Sugar Shack! My feel-good, bright, clean and cozy and 2 bedroom / 2 bath cottage nestled in the woods off a quiet street. Stylish, comfortable, and perfect for a couple or small family. With just-renovated kitchen and bathrooms- it’s vintage charm meets modern comfort in spaces that feel fresh and connected to their roots. And comfy beds and 100% organic cotton bedding- a must! Enjoy the privacy and total comfort of a country setting and the ease of proximity to town.

Top guest favourite

Guest suite in Pleasantville

4.84 out of 5 average rating, 73 reviews

Charming Studio Centrally Located in Pleasantville

Private Studio Apartment with private entrance. Queen-sized bed + sofa bed. Cozy-space w/ big windows in a big home centrally located in the beautiful small town of Pleasantville. 5 min walk to MetroNorth Train to NYC (45 train ride), Pace University, TONS of bars & restaurants, coffee shops, Jacob Burns Film Center, cute shops. One of the best walking towns in Westchester County. Amazing outdoor activities close by. Friendly host nearby in main house for any questions!

Top guest favourite

Treehouse in Wallkill

4.99 out of 5 average rating, 317 reviews

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 favourite

Guest suite in Haverstraw

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:)

Top guest favourite

Home in Mount Kisco

4.94 out of 5 average rating, 147 reviews

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!

Top guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 580 reviews

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

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Other great holiday rentals in Chappaqua

Top guest favourite

Home in Valhalla

5 out of 5 average rating, 15 reviews

Valhalla Home

MichaelRating, 5 stars1 week ago

A perfect spot for visiting Westchester. Easy access to the City and easy access to Tarrytown etc... The place was great. A big space in a super cool 50s era house with super modern amenities.

Superhost

Home in Ossining

4.84 out of 5 average rating, 146 reviews

Lower Hudson Valley Idyllic Retreat

ThomasRating, 5 stars5 months ago

Rory‘s place was amazing. This house is not only secluded, but it’s nestled in its own little mountain hideaway. The house itself is something out of a ski resort with magnificent rock features indoors and out very spacious The grounds are perfect for animals. High fence around the whole property With gate definitely be staying here again.

Guest favourite

Guest suite in Croton-on-Hudson

4.88 out of 5 average rating, 16 reviews

Mountain Edge: Spacious Suite

NefretyreeRating, 5 stars2 weeks ago

We stayed here after a long night of travel. It was a beautiful location on the way to our final destination. It was peaceful and easy to sleep during the day. The air conditioning was nice. It was cool when we arrived and felt very cozy. The queen bed was incredibly comfortable. It was perfect for what we needed, but we wish we could have been awake longer to enjoy the scenery longer.

Guest house 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!

Home in Philipstown

5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago

Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.

Guest favourite

Home in Mount Kisco

5 out of 5 average rating, 7 reviews

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!

Guest favourite

Guest house in Armonk

5 out of 5 average rating, 5 reviews

Guest House in Armonk

ElizabethRating, 5 stars3 weeks ago

This place was exactly what I needed after a chaotic week of my family’s estate sale. It was about the quietest Airbnb I’ve ever been in. The owners were so kind and attentive. I absolutely loved it, and will definitely book again if need be. I would rate it a perfect 10

Guest favourite

Home in Briarcliff Manor

4.94 out of 5 average rating, 17 reviews

Comfortable Cottage

MaryannRating, 5 stars3 days ago

Stayed to attend a wedding over the weekend. The home was cozy, clean and comfortable. I was sad that I was only staying to attend an event because their kitchen is pretty neat and would have loved to make a nice meal. It's a peaceful home and the bedrooms are private from one another. Check-in instructions were clear and Lara was responsive when needed. I would stay here again.

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Holiday rentals in Chappaqua

Top-rated holiday rentals in Chappaqua

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