Search Holiday Rentals in Chappaqua

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Chappaqua

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (2)
"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"
The price is £576
includes taxes & fees
29 Jun - 30 Jun
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (20)
"Easy entrance and exit policy. Great communication from owners. Perfect location. "
The price is £869
includes taxes & fees
8 Jul - 9 Jul
Waterview House Walking Distance from Cove Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is £365
includes taxes & fees
26 Jun - 27 Jun
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"Great home with fun ping pong table!"
The price is £1,712
includes taxes & fees
29 Jun - 30 Jun
New Beach Home near Stamford Downtown/Shippan

The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

The price is £413
includes taxes & fees
1 Jul - 2 Jul
The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
The price is £433
includes taxes & fees
30 Jun - 1 Jul
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

The West Lane Inn - Queen Room

9.4 out of 10, Exceptional, (3)
"Vert nice property, very nice and accommodating proprietor and staff."
The price is £317
includes taxes & fees
2 Jul - 3 Jul
The West Lane Inn - Queen Room

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

8.0 out of 10, Very good, (2)
"It was beautiful and quite. A hidden gem."
The price is £201
includes taxes & fees
30 Jun - 1 Jul
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

10.0 out of 10, Exceptional, (1)
"Wow! I wish we could have stayed here more than just one night! The host was so accommodating of our last-minute reservation and provided friendly and thoughtful assistance throughout our stay. This home is stunning! Careful planning and top-of-the-line finishes clearly went into every detail of this beautiful family home and we were so comfortable in every space. Larchmont train station is just steps away and made our travel to NYC a breeze. The home truly has a park-like feel and the house is...
The price is £1,624
includes taxes & fees
2 Jul - 3 Jul
Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

Luxury 3Bed Private Apartment Near Manhattan

9.0 out of 10, Wonderful, (16)
"Host was very accommodating and easy to communicate with!"
The price is £509
includes taxes & fees
30 Jun - 1 Jul
Luxury 3Bed Private Apartment Near Manhattan

Upscale Relax near Yankee Stadium, and Columbia University "14 min drive"

2.0 out of 10, (1)
"The sheets were way over bleached and burned my skin. The bed is way too soft and the sofa is uneven and sinks. The area is quite scary especially at night, and it is surrounded by vacant lots and construction zones. Most of the other stores in this building are closed, and homeless people walking around. The cleaning products use have a distinctively bad smell that even the air conditioning couldn’t eliminate, and the air conditioners are so loud you can’t hear the tv if they are running."
The price is £267
includes taxes & fees
1 Jul - 2 Jul
Upscale Relax near Yankee Stadium, and Columbia University "14 min drive"

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is £321
includes taxes & fees
2 Jul - 3 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Luxury NY Home with Free Parking

4.0 star property
Luxury NY Home with Free Parking

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

10.0 out of 10, Exceptional, (15)
"Wonderful, comfortable home! Clean, user-friendly with great views!"
The price is £651
includes taxes & fees
30 Jun - 1 Jul
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Comfortable 1 family home in Tuckahoe that's near train

The price is £533
includes taxes & fees
30 Jun - 1 Jul
Comfortable 1 family home in Tuckahoe that's near train

TheVictorianBlue|25min to NYC

9.6 out of 10, Exceptional, (5)
"The accommodations were fantastic, with spacious rooms, modern amenities, and breathtaking views. Additionally, the host was incredibly accommodating, ensuring that every aspect of my stay was comfortable and enjoyable. I highly recommend this property to anyone looking for a perfect getaway with a gracious host!"
The price is £1,118
includes taxes & fees
30 Jun - 1 Jul
TheVictorianBlue|25min to NYC

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

The price is £242
includes taxes & fees
18 Jul - 19 Jul
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is £565
includes taxes & fees
26 Jun - 27 Jun
3BR Prime Luxury near NYC w Arcade Room

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

8.0 out of 10, Very good, (16)
"Great place great location"
The price is £102
includes taxes & fees
5 Jul - 6 Jul
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
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

Frequently asked questions

Can I find a holiday rental in Chappaqua?

Yes, there are holiday rentals close to the most popular sights in Chappaqua, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Chappaqua has to offer?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside Chappaqua is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Chappaqua?

Expedia has 3 holiday rentals for your stay in Chappaqua.

What’s there to see and do in Chappaqua?

Explore the area and family-friendly sights such as Bruce Museum of Arts and Science, or get out into nature at a spot like Hardscrabble Wilderness Area. Travelers Rest and Thomas J. Watson Research Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Chappaqua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chappaqua. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.