Search Vacation Homes in Chappaqua

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chappaqua

Our top choices for Chappaqua vacation homes

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

10.0 out of 10, Exceptional, (87)
"It was very nice "
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, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is SAR 657
SAR 1,318 total
includes taxes & fees
4 Sep - 5 Sep
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (60)
"We booked this home for seven adults and had plenty of room! Everyone remarked on how lovely the house was in the location on the water. Great communication with the property owner. We went into the city most days and this was a great place to come back to all the comforts of Home and More!"
Waterfront Retreat Center for Health & Wellness

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

9.8 out of 10, Exceptional, (18)
"The house was very clean and the check-in process was smooth. Host was very responsive. Overall we loved our stay and would definitely book again next time we're in the area!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

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!

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (10)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!

Spacious 4-bedroom house in charming Rye with AC

The price is SAR 751
SAR 1,707 total
includes taxes & fees
3 Sep - 4 Sep
Spacious 4-bedroom house in charming Rye with AC

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! "
The price is SAR 557
SAR 1,099 total
includes taxes & fees
3 Sep - 4 Sep
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is SAR 1,415
SAR 1,954 total
includes taxes & fees
3 Sep - 4 Sep
Modern Luxury Home w GameRoom & Parking

Cozy 2 Bedroom, Near NYC, Easy Parking

10.0 out of 10, Exceptional, (2)
"Owners very responsive. I didn’t see message with check-out process (garbage etc) until after I left so I would suggest including with listing or providing upon check-in. Place was very clean! Easy on street parking. Only two towels though, for two females for two days. Not a huge deal but would have liked one or two more. "
Cozy 2 Bedroom, Near NYC, Easy Parking

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (4)
"Beautiful home and great host!"
Serene Hudson Valley Escape w/ Pool & Grill

La Casita Bonita near NYC

5.0 out of 10, (2)
"Convenient location to upstate snd downtown NYC. All the rooms were good size. Appreciate the welcoming outside space both out front and in the back area. Plan to come back later this year."
La Casita Bonita near NYC

Charming 3-bedroom house.

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property was very clean and nicely furnished. A nice quiet spot."
Charming 3-bedroom house.

Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Lovely home for a get away. "
Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

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

10.0 out of 10, Exceptional, (3)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy

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

2.0 star property
9.8 out of 10, Exceptional, (12)
"We had a great stay here visiting family. Great location and a very easy process. Francesca was very attentive. We will come back here next time. Do not hesitate to book. "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Harriman Outdoor Center - White Oak Cabin

The price is SAR 799
SAR 929 total
includes taxes & fees
7 Sep - 8 Sep
Harriman Outdoor Center - White Oak Cabin

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

10.0 out of 10, Exceptional, (5)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is SAR 682
SAR 1,189 total
includes taxes & fees
29 Sep - 30 Sep
Lovely 3BR Home with parking-Walk to WP Gate!

New Jersey home, close to NY City Fun!

8.8 out of 10, Excellent, (6)
"My family and I stayed at Gloria's place for a few days to attend the funeral of our grandmother. The house was perfect for all of our needs and Gloria made us feel at home. "
New Jersey home, close to NY City Fun!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chappaqua Hotel Reviews