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Compare 345 Vacation Homes in Chappaqua with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (9)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

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

10.0 out of 10, Exceptional, (35)
"Cozy property with great amenities and a perfect location for decompressing after visiting family. we will stay here again!"
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (30)
"Its was perfect, quiet and spacious great little get away."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (11)
"Location was great! Having a car with off street parking, walk to station and well lit. Very clean, hot hot water (which I loved!) and plenty in the kitchen! Thank you!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (14)
"Host was very accommodating and easy to communicate with!"
The price is AED 1,194
AED 2,218 total
includes taxes & fees
18 May - 19 May
Luxury 3Bed Private Apartment Near Manhattan

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Very convenient and plenty of room. Easy to get to NY from Stamford train station and everything we needed nearby."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (18)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is AED 918
AED 1,587 total
includes taxes & fees
15 May - 16 May
Contemporary Cozy Cottage

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (24)
"great place beautiful setting. The house looks nicer than what is actually in the listing. Comfortable place, very clean, had everything we needed. "
Modern, Magical Woodsy Escape 1 Hour From NYC

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
New Beach Home near Stamford Downtown/Shippan

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
10.0 out of 10, Exceptional, (1)
"I have stayed in several vacation homes in Nyack. Some were swankier, most were cleaner or better stocked, but none was more comfortable or in a better location. The neigborhood is quiet, the house has loads of privacy, and you can easily walk to anything in town. There is a short but very steep part on this walk, so bring some sneakers if walking in town is your thing. This is the perfect place to stay if you want to feel as though you LIVE in Nyack. This was my fourth stay at this house. "
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (3)
"Close to west point where we were able to attend the sporting event. It is walking distance to the small town outside campus where you can find local shops for eating or shopping. ."
The price is AED 455
AED 897 total
includes taxes & fees
14 May - 15 May
Lovely 3BR Home with parking-Walk to WP Gate!

Charming Hudson Valley 3-Bedroom Family Getaway

8.0 out of 10, Very Good, (2)
"We recently stayed here while visiting our son at West Point. The house is a nice older home that provided us what was needed. We were not able to check in until well after dark so we did have look closely to determine if we had the correct house. An outside light would have been helpful. Overall nice stay"
The price is AED 420
AED 903 total
includes taxes & fees
14 May - 15 May
Charming Hudson Valley 3-Bedroom Family Getaway

Cozy and beautiful house

9.8 out of 10, Exceptional, (24)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan

Ossining Vacation Rental Near River, Trails & MTA!

7.6 out of 10, Good, (8)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house

Luxe Living: Pool, Playground & Fireplace

10.0 out of 10, Exceptional, (1)
Luxe Living: Pool, Playground & Fireplace

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Updated, well equipped kitchen and comfortable living and sleeping spaces. We will definitely try to book here on our next visit to West Point. "
The price is AED 1,653
AED 3,037 total
includes taxes & fees
14 May - 15 May
West Point Family Retreat, 5 min walk to Thayer!

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

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
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

3.0 star property
6.0 out of 10, (29)
"Convenience. Full kitchen and spacious rooms"
The price is AED 632
AED 727 total
includes taxes & fees
30 May - 31 May
Stamford Suites

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"Vibe and aesthetic was lovely - near downtown restaurants, wonderful time will come back "
Luxury Apartments by Hyatus at The Asher
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.