Chappaqua Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chappaqua vacation rentals

3 bedrooms, desk, iron/ironing board, free WiFi

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
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.
The price is ￥20,760
￥70,134 total
includes taxes & fees
Feb 10 - Feb 11
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Luxury House, Garden View | Dining

Apartment in Southeast Yonkers

Modern Comfort in the Heart of NYC
4.0 star property
The price is ￥71,312
￥100,224 total
includes taxes & fees
Jan 31 - Feb 1
Modern Comfort in the Heart of NYC
Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥11,727
￥51,235 total
includes taxes & fees
Jan 26 - Jan 27
House on the Babbling Brook- Quiet 2BR + King Bed!
TV

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
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.
The price is ￥14,814
￥30,233 total
includes taxes & fees
Feb 4 - Feb 5
Cozy 1-bedroom retreat minutes from West Point!
Living area

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is ￥87,159
￥123,301 total
includes taxes & fees
Jan 24 - Jan 25
Luxury NYC Home Game Room Free Parking
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥11,885
￥39,242 total
includes taxes & fees
Jan 26 - Jan 27
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is ￥15,847
￥41,738 total
includes taxes & fees
Jan 26 - Jan 27
Elegant Hideaway with Free Parking
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
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.
The price is ￥14,104
￥58,742 total
includes taxes & fees
Jan 25 - Jan 26
Local Artist Inspired | Walk to WestPoint + King Bed
TV, fireplace

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥26,385
￥56,073 total
includes taxes & fees
Jan 25 - Jan 26
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Luxury House | Living area

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is ￥31,536
￥50,969 total
includes taxes & fees
Jan 26 - Jan 27
Spacious 3BR Luxe Escape near NYC
Luxury Villa, Garden View | Dining

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is ￥71,312
￥107,789 total
includes taxes & fees
Jan 24 - Jan 25
Luxury NYC Home with Free Parking for 12
Exterior detail

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Luxury Villa, Patio | Living area

Villa in Bryn Mawr

Luxury 5 BR Home Free Parking
2.0 star property
The price is ￥103,006
￥138,851 total
includes taxes & fees
Jan 24 - Jan 25
Luxury 5 BR Home Free Parking
Living area

Apartment in Bryn Mawr

Uscale 2BR Escape in the Heart of NYC
2.0 star property
The price is ￥23,771
￥51,790 total
includes taxes & fees
Jan 25 - Jan 26
Uscale 2BR Escape in the Heart of NYC
Interior

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥28,962
￥55,211 total
includes taxes & fees
Feb 4 - Feb 5
Lovely 3BR Home with parking-Walk to WP Gate!
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is ￥17,432
￥43,115 total
includes taxes & fees
Jan 25 - Jan 26
Luxe 1BR Oasis - Prime NY Stay
Property grounds

Cottage in Greenwich

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
10.0 out of 10, Exceptional, (1 review)
"The location was perfect for our family getaway. The snow and river backdrop brought the holiday spirit out in our college age kids. There was plenty of room and the fireplace was great. All the appliances are high end and the communication was excellent. The host went out of his way to make the visit special. Would highly recommend "
United States
Scott and Linsay T.
The price is ￥83,001
￥166,785 total
includes taxes & fees
Jan 29 - Jan 30
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Property grounds

Vacation Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is ￥21,251
￥43,456 total
includes taxes & fees
Feb 21 - Feb 22
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Private kitchen

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
The price is ￥15,689
￥41,165 total
includes taxes & fees
Jan 25 - Jan 26
Luxury 1BR located in Prime Yonkers Area
House | 5 bedrooms

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is ￥80,539
￥169,226 total
includes taxes & fees
Jan 28 - Jan 29
NEW 45 Wolden Rd Ossining NY 10562
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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Top Chappaqua Hotel Reviews

Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

10/10 Excellent
"The place is very clean and the manager Jocelyn is great"
Steve 1-night trip
Posted 2 days ago
Ramada by Wyndham Bronx

Find out more about Chappaqua

Search for holiday rentals in Chappaqua on Expedia! You can easily find your home rentals, villas, holiday apartments in Chappaqua using one of the methods below:

  • View our selection of featured holiday rentals in Chappaqua
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  • Enter your travel dates to view the best deals on holiday rentals in Chappaqua while they last

Look no further and take a look at our great range of rental properties in Chappaqua!

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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Chappaqua is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Grand Prix New York / Spins Bowl, or get out into nature at a spot like Hardscrabble Wilderness Area. Thomas J. Watson Research Center and Teatown Lake Reservation 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.