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Vacation Homes in Chappaqua

Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
$259 nightly
The price is $293
Aug 6 - Aug 7
Total includes taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Historic Connecticut Home w/ Grill & Spacious Yard
Dining

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (12)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard
Stylish Stay in City’s Best Spot- The Perfect Stay
Outdoor dining

Stylish Stay in City’s Best Spot- The Perfect Stay

3.0 out of 10, (2)
"I arrived in New York on 6-22-25 I requested the check in information in which the host refused to give. She stated the cleaner hadn't showed up to clean the property so she gave me another address. Well this place had multiple stairs and was located on the 2nd floor which couldn't accommodate the group I was with. When I informed the host she gave me another address which was smaller with one bathroom. Smaller than the original one booked. After explaining that this wouldn't work the host...
Stylish Stay in City’s Best Spot- The Perfect Stay
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Microwave, oven, stovetop, dishwasher

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Charming Highland Falls Home < 2 Mi to West Point!
Exterior

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
$616 nightly
The price is $699
Sep 3 - Sep 4
Total includes taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Beach

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Spacious 4-bedroom house in charming Rye with AC
Miscellaneous

Spacious 4-bedroom house in charming Rye with AC

$454 nightly
The price is $454
Aug 6 - Aug 7
Total includes taxes and fees
Spacious 4-bedroom house in charming Rye with AC
Luxury NY Home 3BR with Easy Parking
Luxury House | Living area | Flat-screen TV

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
$476 nightly
The price is $521
Aug 7 - Aug 8
Total includes taxes and fees
Luxury NY Home 3BR with Easy Parking
St Julian's Place - Large updated Apt @ 40 Min NYC
Property grounds

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"This is the 3rd time we've stayed here. The apartment looks great and is convenient for us to visit family. We always enjoy staying here."
St Julian's Place - Large updated Apt @ 40 Min NYC
Contemporary Cozy Cottage
Interior

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (26)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
$367 nightly
The price is $420
Aug 6 - Aug 7
Total includes taxes and fees
Contemporary Cozy Cottage
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Fridge, microwave, stovetop, dishwasher

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Aspen In Airmont NY
Private kitchen

Aspen In Airmont NY

10.0 out of 10, Exceptional, (6)
"We had an excellent stay in this beautiful house. Favorite thing is the magnificent dining table."
Aspen In Airmont NY
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Fridge, microwave, oven, stovetop

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great location, quite dead end. Excellent value, we had a very comfortable stay.Walking distance to the station for Metro North into NYC. Great deli just around the corner. Responsive hosts, will gladly use again!! "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0 out of 10, Exceptional, (3)
"The house was big enough for 2 families. It was very clean and comfortable. The property is beautiful and Cold Springs was the perfect spot for everything we wanted to do while in NY. The caretakers were very responsive and accommodating. We would definitely stay here again. "
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Lake Carmel Access: Waterfront Home w/ Deck!
Fridge, microwave, stovetop, dishwasher

Lake Carmel Access: Waterfront Home w/ Deck!

10.0 out of 10, Exceptional, (1)
"Love the home wonderful location. The view is breathtaking. The owner responded timely to any request. "
Lake Carmel Access: Waterfront Home w/ Deck!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chappaqua Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Room was spotless, bed was comfortable, front desk was super friendly. The cleaners were super nice every morning. The pool/hot tub was a nice touch. Highly recommend to anyone looking to stay in the area. "
Joshua 2-night trip
Posted 2 days ago
Hyatt Regency Greenwich