Chappaqua Holiday Rentals

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Holiday Rentals in Chappaqua

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is NZ$249
includes taxes & fees
1 Sept - 2 Sept
Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is NZ$1,287
includes taxes & fees
15 Aug - 16 Aug
3BR Prime Luxury near NYC w Arcade Room

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 NZ$529
includes taxes & fees
11 Sept - 12 Sept
Guesthouse at Norwalk Inn

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

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 NZ$547
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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 NZ$1,233
includes taxes & fees
17 Aug - 18 Aug
Modern Luxury Home w GameRoom & Parking

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

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

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

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

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

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

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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 NZ$226
includes taxes & fees
19 Aug - 20 Aug
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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

10.0 out of 10, Exceptional, (1)
"I chose this apartment for its location primarily and it was a hit. Since we were traveling and staying for two weeks with a toddler and a new baby I was looking for it to also have an outdoor space, and it was wonderful as seen in the pictures. For personal reasons I had to change my dates a few days before my booking was coming up, the hosts had no problem to accommodate my needs. During our stay, we even had the opportunity to meet the neighbor next door and visit her garden. The neighborhood...
The price is NZ$540
includes taxes & fees
8 Sept - 9 Sept
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

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 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

Piermont Oasis

10.0 out of 10, Exceptional, (2)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
The price is NZ$363
includes taxes & fees
9 Sept - 10 Sept
Piermont Oasis

Private lake escape

Private lake escape

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 NZ$874
includes taxes & fees
17 Aug - 18 Aug
Luxury NY Home 3BR with Easy Parking

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

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

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.