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Compare 247 Vacation Homes in Chappaqua with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
The price is AED 2,222
AED 4,135 total
includes taxes & fees
2 Dec - 3 Dec
New Beach Home near Stamford Downtown/Shippan

Entire house with Hot Tub 25 Mins to Manhattan

9.0 out of 10, Wonderful, (2)
"We were so pleased with the peace we felt while staying at this property. We loved the set up. The neighborhood was quiet and reminded us of home. This helped us, as a family, to grieve as we were attending a family member’s funeral. We’d love to stay again under different circumstances. Thank you for everything. "
The price is AED 738
AED 1,329 total
includes taxes & fees
1 Dec - 2 Dec
Entire house with Hot Tub 25 Mins to Manhattan

LUXE 3BD/2BA 29 min>NYC w/Parking & deck

10.0 out of 10, Exceptional, (13)
"The listing is accurate, perfect location to walk to train, restaurants and so much more! We were delighted to stay there and we look forward to staying in the future!! Thanks Dan"
LUXE 3BD/2BA 29 min>NYC w/Parking & deck

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (3)
"Beautiful cozy home. Well stocked. Good communication with management/owners Overall great experience!!! ❤️"
Charming Highland Falls Home < 2 Mi to West Point!

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

10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (18)
"Great space. Clean sheets and towels. Wonderful shower. Great balcony I highly recommend!"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

1-bedroom vacation home 12 minutes from Bronx Zoo

9.8 out of 10, Exceptional, (22)
"Very clean! Great hospitality! Will definitely book again. "
1-bedroom vacation home 12 minutes from Bronx Zoo

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

10.0 out of 10, Exceptional, (28)
"Beautiful property, with cozy linens in every room, incredibly well maintained property, and lovely views. The welcome book had clear instructions, there were great lawn games, lots of suggestions to eat too. The icing on the cake was the welcome basket, complete with Halloween treat bag for our little one! "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

9.4 out of 10, Exceptional, (8)
"Great place for a group of friends to use as homebase for some shows at the Capitol Theater. "
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

Cozy and beautiful house

10.0 out of 10, Exceptional, (19)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (22)
"House was beautifully furnished with lovely touches of art work and lovely succulent plants. The hot tub was a great touch, and we enjoyed it every morning. The children loved exploring the property. Thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Beautiful downstairs apartment. Walk to town, train, & beach ferry!

10.0 out of 10, Exceptional, (16)
"My stay was unique because my daughter was having a baby and I wasn’t 100% sure of the dates, and Henri was so kind and accommodating and flexible. It really was a very special stay."
Beautiful downstairs apartment. Walk to town, train, & beach ferry!

Ossining Vacation Rental Near River, Trails & MTA!

7.6 out of 10, Good, (5)
"This house was wonderful! Had a lot of space and it was perfect. Feliciano was very receptive, even helped open the door remotely for me when I had a hard time getting in at check in. Responded immediately. Would book again!"
Ossining Vacation Rental Near River, Trails & MTA!

Amazing 3BR/3BA! Croton on Hudson!

7.0 out of 10, Good, (2)
"We found the house pleasant and centrally located"
Amazing 3BR/3BA! Croton on Hudson!

Cozy House 3 Blocks From West Pt

9.8 out of 10, Exceptional, (6)
"Perfect location very close to Thayer Gate, West Point Museum, Visitors Center and local restaurants in Highland Falls. Host is an excellent communicator and has put a lot of thought into this clean and comfortable home. Cannot wait to visit again soon. "
Cozy House 3 Blocks From West Pt

Up-to-date Home w/ Pool, Playground & Fireplace!

Up-to-date Home w/ Pool, Playground & Fireplace!

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is AED 1,649
AED 3,100 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
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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Other property types in Chappaqua

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AED 621
AED 695 total
includes taxes & fees
29 Nov - 30 Nov
Stamford Suites

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"This is my second state at the New Dawn house and it was just as wonderful as last year. I can't think of a better place for a large gathering in the Bronx area. "
Waterfront Retreat Center for Health & Wellness

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 904 total
includes taxes & fees
2 Dec - 3 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.