Search Vacation Homes in Chappaqua

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 285 Vacation Homes in Chappaqua with updated reviews, rates, and availability.

Cozy and beautiful house

10.0 out of 10, Exceptional, (21)
"A movie was being produced at our home.We needed to relocate for the week.We loved the house. All the rooms were clean & organized . Kitchen was well equipped .We met the neighbors! Lovely people !The only draw back is the stairs. Bathrooms are upstairs & in finished basement , but otherwise lovely"
Cozy and beautiful house

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

10.0 out of 10, Exceptional, (32)
"Hot tub was awesome. Near bear mountain, also relatively easy train access to NYC across bridges."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

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

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (21)
"The perfect location just one hour north of New York City to host a weekend leadership summit."
Modern, Magical Woodsy Escape 1 Hour From NYC

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"It was a quick trip to see woman’s army basketball game. It was an excellent stay and excellent accommodations. "
The price is AED 918
AED 1,359 total
includes taxes & fees
20 Mar - 21 Mar
Contemporary Cozy Cottage

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

2.0 star property
9.4 out of 10, Exceptional, (6)
"My sister and I booked this apartment because we were coming down for my Grandnephew’s Christening. It couldn’t have been more perfect. We were within 5 minutes of every venue for the stay. Greg and Francesca were just amazing. Answering any and all questions we asked. Located on a dead end street which was so quiet.at night. Would definitely recommend this apartment.. Pristine and very roomy."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

Charming 3-bedroom house with AC, WiFi in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (15)
"The home was clean and the area is beautiful! It was a wonderful experience staying in a historic home and the owners were fantastic!"
Historic Hideaway with Lake Access!

Chill Vibes & Luxe Living: Pool, Playground & Fire

10.0 out of 10, Exceptional, (1)
Chill Vibes & Luxe Living: Pool, Playground & Fire

'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!

Modern Farmhouse Walking Distance to West Point

9.2 out of 10, Wonderful, (7)
"A second stay at this home. The location truly can't be beat at this cozy historic home. The home has lots of charm from the wood floors, to the covered front porch, to the nice backyard. Restaurants and Pubs are a quick walk, a wine store is a few paces away for that relaxing end-of-night glass. I previously reviewed the place and noted a lack of a baking sheet (as did a prior reviewer). We purchased one for the kitchen on our stay as well as a stock pot - cold night air called for a pot...
Modern Farmhouse Walking Distance to West Point

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

10.0 out of 10, Exceptional, (38)
"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.

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

10.0 out of 10, Exceptional, (76)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (11)
"Host was very accommodating and easy to communicate with!"
The price is AED 1,194
AED 1,943 total
includes taxes & fees
19 Mar - 20 Mar
Luxury 3Bed Private Apartment Near Manhattan

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (19)
"This property worked out perfectly for our family group. We needed a home that could accommodate 14 people across 3 generations comfortably and this property definitely addressed our needs. The home is huge, very well laid out, and well appointed. It was very clean and functional. It had a nice homey feel and wasn't cluttered with the owner's things. Some specifics:• There are a LOT of spacious bedrooms. Most have en-suite bathrooms, which is great.• The main level is well laid out and has lots...
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is AED 1,212
AED 2,773 total
includes taxes & fees
16 Mar - 17 Mar
New Beach Home near Stamford Downtown/Shippan

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (95)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

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

10.0 out of 10, Exceptional, (13)
"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...
The price is AED 1,833
AED 3,360 total
includes taxes & fees
18 Mar - 19 Mar
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.
Don't see what you're looking for?
See all available properties in Chappaqua
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chappaqua

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (29)
"I was very impressed with this "hotel". It is more of an AirBB as your unit is an apartment in an apartment building with permant residents. It comes nicely furnished, including basic kitchen essentials (like service for four, pots and pans, coffee maker, etc). All of the amenities are modern, and the in-unit washer dryer is a huge plus. I also really appreciated some of the welcome gifts, including some coffee/tea, laundry detergent, and your basic hygiene essentials. Property communicates...
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is AED 647
AED 744 total
includes taxes & fees
28 Mar - 29 Mar
Stamford Suites

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is AED 617
AED 911 total
includes taxes & fees
18 Mar - 19 Mar
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.