Chappaqua Vacation Rentals

  • 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

In two weeks
In two months
In three months
In four months

Our top choices for Chappaqua vacation rentals

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$173 nightly
The price is $188
Feb 4 - Feb 5
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$296 nightly
The price is $309
Feb 4 - Feb 5
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Feb 4 - Feb 5
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
$232 nightly
The price is $260
Feb 4 - Feb 5
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
$240 nightly
The price is $275
Feb 4 - Feb 5
Total with taxes and fees
Elegant Hideaway with Free Parking

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
$243 nightly
The price is $272
Feb 4 - Feb 5
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
$249 nightly
The price is $285
Mar 2 - Mar 3
Total with taxes and fees
Luxury 3BR Home Game Room Free Parking

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$402 nightly
The price is $408
Feb 4 - Feb 5
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$291 nightly
The price is $329
Feb 4 - Feb 5
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (26 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
$213 nightly
The price is $241
Feb 22 - Feb 23
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$257 nightly
The price is $279
Feb 4 - Feb 5
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (13 reviews)
"Absolutely perfect location--so lovely to walk to restaurants, ice cream, views, etc. Would definitely stay here again."
United States
joelle a.
$186 nightly
The price is $207
Feb 10 - Feb 11
Total with taxes and fees
Piermont Oasis

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$378 nightly
The price is $384
Feb 4 - Feb 5
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
$292 nightly
The price is $327
Feb 4 - Feb 5
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (96 reviews)
"Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford."
United States
Fatima
$130 nightly
The price is $150
Feb 4 - Feb 5
Total with taxes and fees
Stamford Suites

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.2 out of 10, Very Good, (18 reviews)
"Great location"
United States
Jordan S.
$115 nightly
The price is $135
Feb 6 - Feb 7
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
$384 nightly
The price is $434
Feb 4 - Feb 5
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed

Two Wash

Two Wash
2.0 star property
Bryn Mawr
$332 nightly
The price is $372
Feb 4 - Feb 5
Total with taxes and fees
Two Wash

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
$680 nightly
The price is $778
Feb 4 - Feb 5
Total with taxes and fees
Luxury NYC Home Game Room Free Parking

Global Luxury Suites White Plains

Global Luxury Suites White Plains
3.5 star property
White Plains
7.0 out of 10, Good, (38 reviews)
"Great location, spacious apartment and clean. The public areas like the hallway needed vacuuming but everything else was great."
United States
Jennifer
$174 nightly
The price is $199
Feb 7 - Feb 8
Total with taxes and fees
Global Luxury Suites White Plains
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

Everything you need to know about Chappaqua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaqua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaqua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaqua. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chappaqua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chappaqua rentals

At Expedia, we put the best Chappaqua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chappaqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaqua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Chappaqua?

Yes, we offer vacation rentals near the most popular sights in Chappaqua, or you can select a secluded option if you're looking for relaxation. Our travelers say Chappaqua has a good selection of restaurants. Make sure you have time to check out the sporting events and entertainment choices during your trip.

What are some of the best vacation home rentals in Chappaqua?

Waterfront Retreat Center for Health & Wellness: This vacation home rental near Chappaqua is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chappaqua?

Expedia has 3 vacation rentals for your stay in Chappaqua.

What’s there to see and do in Chappaqua?

Explore the area and family-friendly sights such as Westchester Skating Academy, or get out into nature at a spot like Hardscrabble Wilderness Area. Thomas J. Watson Research Center and Rockefeller State Park Preserve are a couple of places you'll find in the larger area.

What’s a vacation rental in Chappaqua like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chappaqua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.