Holiday houses in Chappaqua

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Top-rated holiday rentals in Chappaqua

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Superhost

Home in Ossining

4.84 out of 5 average rating, 146 reviews

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.

Guest favourite

Apartment 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, 154 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.

Top Guest favourite

Guesthouse in Mahopac

4.95 out of 5 average rating, 235 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Guest favourite

Apartment 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.

Guest favourite

Barn in Katonah

4.97 out of 5 average rating, 124 reviews

The Magic Red Barn with heated pool now opened!

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

Top Guest favourite

Apartment in Ossining

4.96 out of 5 average rating, 441 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

Apartment 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!

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:)

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Other great holiday rentals in Chappaqua

Top Guest favourite

Treehouse in Wallkill

4.99 out of 5 average rating, 317 reviews

The Treecastle at the Roundhouse Homestead

FrankRating, 5 starstoday

Our weekend here was exactly what we were looking for, peaceful getaway in a treehouse?! Heck yes. It was a great place to unplug and really relax, quiet with no sounds of traffic. Dan and Melissa were so responsive and friendly which really allowed us to unwind and feel at home. They really thought of everything to make our stay easy and even left home baked good which were beautifully displayed upon our arrival. It’s so private and they really separated this section from their home. The way it’s laid out and the space they used, they truly made it as if it was your getaway in your own little world. Summary: it’s built with love and you can truly feel that they take pleasure in giving others the ability to create their own memories.

Guesthouse in Bedford Hills

4.88 out of 5 average rating, 133 reviews

Barrett's Sanctuary

ReginaRating, 5 stars1 week 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!

Top Guest favourite

Cottage in Weston

4.97 out of 5 average rating, 143 reviews

The River Loft

GabeRating, 5 stars6 days ago

The River Loft was truly amazing . Tom had wine and smores supplies for us and the place looks exactly like the pictures. Truly a great place to be.

Guest favourite

Guesthouse in Chappaqua

4.94 out of 5 average rating, 88 reviews

Cozy 2 Bedroom Cottage in Stunning Setting

CandiceRating, 5 stars2 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 stars2 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!

Top Guest favourite

Guest suite in Stamford

4.94 out of 5 average rating, 140 reviews

Charming Retreat in North Stamford

DawnRating, 5 stars1 month ago

If I'm in the Stamford area again, I'll definitely book here. This space was just perfect for me. I found the wooded area, birds singing and the overall area ideal. I felt very safe and comfortable. There is a family that lives upstairs, with pups, so expect some sounds from above but nothing disturbing or out of hours. This is a gorgeous residential area. The place was very clean, the bed was so comfortable and everything provided was far more than sufficient for my needs. Everything was just so easy and smooth. I had no reason to contact Julita for anything.

Guest favourite