Chappaqua Vacation Rentals

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Our top choices for Chappaqua vacation rentals

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 10 - Feb 11
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (98 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 23 - Feb 24
Total with taxes and fees
Stamford Suites

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
$240 nightly
The price is $275
Feb 10 - Feb 11
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 22 - Feb 23
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$330 nightly
The price is $380
Feb 16 - Feb 17
Total with taxes and fees
Guesthouse at Norwalk Inn

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
$332 nightly
The price is $372
Feb 10 - Feb 11
Total with taxes and fees
Luxury 3BR Family Home Game Room Parking

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
$287 nightly
The price is $322
Feb 10 - Feb 11
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC

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 10 - Feb 11
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC

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

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$333 nightly
The price is $371
Feb 10 - Feb 11
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking

Two Wash

Two Wash
2.0 star property
Bryn Mawr
$332 nightly
The price is $372
Feb 10 - Feb 11
Total with taxes and fees
Two Wash

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
$217 nightly
The price is $248
Feb 12 - Feb 13
Total with taxes and fees
Global Luxury Suites White Plains

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
$178 nightly
The price is $187
Feb 16 - Feb 17
Total with taxes and fees
NY Luxury Apt Free Parking in PRIME Area

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
$351 nightly
The price is $404
Feb 10 - Feb 11
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1 review)
"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
$364 nightly
The price is $408
Feb 10 - Feb 11
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
$611 nightly
The price is $680
Feb 11 - Feb 12
Total with taxes and fees
Luxury NYC Home with Free Parking for 12

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
$518 nightly
The price is $579
Feb 10 - Feb 11
Total with taxes and fees
Luxury 3 BR Near NYC with Easy Parking

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 10 - Feb 11
Total with taxes and fees
Luxury NYC Home Game Room Free Parking

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
$836 nightly
The price is $932
Mar 2 - Mar 3
Total with taxes and fees
NEW 45 Wolden Rd Ossining NY 10562

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
$287 nightly
The price is $322
Feb 10 - Feb 11
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
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

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 $135 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 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.