Search Vacation Homes in Chappaqua

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chappaqua

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (20)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$181 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
$291 nightly
The price is $329
Nov 7 - Nov 8
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
3BR West Point Retreat-3min to Back Gate+ King Bed
9.4 out of 10, Exceptional, (3)
"Home was very peaceful and serene, My Boys really enjoyed the relaxing and laid back vibe this stay had to offer. My kids did mention it would be a summer vacation stay, because of the creek in the back. Overall is was clean and accommodating. Host did their best for all my accommodation. I would give them a 5- Star White Glove on this. Thanks, Hope to revisit! "
United States
Akail S.
$393 nightly
The price is $445
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
2.0 star property
$120 nightly
The price is $137
Nov 7 - Nov 8
Total with taxes and fees
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Nov 13 - Nov 14
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."
United States
James W.
$311 nightly
The price is $352
Nov 17 - Nov 18
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
10.0 out of 10, Exceptional, (7)
"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"
United States
Helen C.
$490 nightly
The price is $555
Nov 9 - Nov 10
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$466 nightly
The price is $473
Nov 17 - Nov 18
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
$297 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$672 nightly
The price is $728
Nov 9 - Nov 10
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
45 Minutes from NYC, Entire House near Stamford Downtown,
10.0 out of 10, Exceptional, (19)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
United States
Lisa B.
$401 nightly
The price is $454
Nov 10 - Nov 11
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (23)
"We had an absolutely amazing time during our stay. The house was beautiful, and Elena was super quick & helpful with answering any questions we had. Both the check in and check out processes were easy and smooth. We had a great time and would highly recommend staying here!"
United States
Matthew O.
$801 nightly
The price is $851
Nov 9 - Nov 10
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Nov 10 - Nov 11
Total with taxes and fees
Contemporary Cozy Cottage
3BR Prime Luxury near NYC w Arcade Room
2.0 star property
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$687 nightly
The price is $769
Nov 7 - Nov 8
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Luxury NY Home with Free Parking
4.0 star property
$558 nightly
The price is $638
Nov 7 - Nov 8
Total with taxes and fees
Luxury NY Home with Free Parking
6 BR, 4 BA Mansion Close to the City
10.0 out of 10, Exceptional, (1)
"Awesome space, perfect for our fall getaway, close to NYC or small town shopping"
United States
Jennifer L.
$680 nightly
The price is $801
Nov 10 - Nov 11
Total with taxes and fees
6 BR, 4 BA Mansion Close to the City
Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
$926 nightly
The price is $1,031
Nov 12 - Nov 13
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
United States
Katy G.
$487 nightly
The price is $525
Nov 9 - Nov 10
Total with taxes and fees
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
9.4 out of 10, Exceptional, (3)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$487 nightly
The price is $525
Nov 11 - Nov 12
Total with taxes and fees
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
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

Find out more about Chappaqua

Chappaqua Vacation Homes information

Number of reviews
139
Accommodation
326 Vacation Homes
Lowest Price
$205
Highest Price
$1,031

Explore a world of travel with Expedia