Chappaqua Holiday Rentals

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Check prices for these dates

Tonight
1 Aug - 2 Aug
Tomorrow
2 Aug - 3 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Chappaqua

Stamford Suites
Lobby

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is HK$1,180
HK$1,357 total
includes taxes & fees
3 Aug - 4 Aug
Stamford Suites
Guesthouse at Norwalk Inn
Property entrance

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is HK$1,884
HK$2,166 total
includes taxes & fees
19 Aug - 20 Aug
Guesthouse at Norwalk Inn
3BR Prime Luxury near NYC w Arcade Room
Terrace/patio

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is HK$4,702
HK$6,037 total
includes taxes & fees
3 Aug - 4 Aug
3BR Prime Luxury near NYC w Arcade Room
Global Luxury Suites White Plains
Reception

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (31)
"This place a marvelous!! Very nice and clean!! The scenery of nature that I experienced when waking up was very refreshing!!"
Global Luxury Suites White Plains
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is HK$1,570
HK$2,478 total
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Cozy Apartment-Just minutes from New York City
Smart TV

Cozy Apartment-Just minutes from New York City

9.2 out of 10, Wonderful, (5)
"Nice place to stay "
Cozy Apartment-Just minutes from New York City
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Luxury Living in the Heart of NY
In-room dining

Luxury Living in the Heart of NY

4.0 star property
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
Luxury Living in the Heart of NY
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Living area

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

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 HK$742
HK$1,058 total
includes taxes & fees
3 Aug - 4 Aug
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Stylish Stay in City’s Best Spot- The Perfect Stay
Outdoor dining

Stylish Stay in City’s Best Spot- The Perfect Stay

3.0 out of 10, (2)
"I arrived in New York on 6-22-25 I requested the check in information in which the host refused to give. She stated the cleaner hadn't showed up to clean the property so she gave me another address. Well this place had multiple stairs and was located on the 2nd floor which couldn't accommodate the group I was with. When I informed the host she gave me another address which was smaller with one bathroom. Smaller than the original one booked. After explaining that this wouldn't work the host...
Stylish Stay in City’s Best Spot- The Perfect Stay
Modern Luxury Home w GameRoom & Parking
Living area

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is HK$3,838
HK$5,071 total
includes taxes & fees
3 Aug - 4 Aug
Modern Luxury Home w GameRoom & Parking
Luxury Apartments by Hyatus at The Asher
Lounge

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher
Private lake escape
Outdoor pool

Private lake escape

Private lake escape
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Exterior

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Luxury NY Home 3BR with Easy Parking
Living area

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
The price is HK$2,959
HK$4,088 total
includes taxes & fees
3 Aug - 4 Aug
Luxury NY Home 3BR with Easy Parking
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
Smart TV

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

The price is HK$1,334
HK$2,532 total
includes taxes & fees
6 Aug - 7 Aug
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

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

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is HK$1,392
HK$2,582 total
includes taxes & fees
4 Aug - 5 Aug
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
Outdoor dining

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Very beautiful greenery area where you can have a drink or breakfast Pool was nice too And bedrooms very calm and comfortable "
ELISE 1-night trip
Posted 2 days ago
Hyatt Regency Greenwich

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 of 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.