Chappaqua Holiday Rentals

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Holiday Rentals in Chappaqua

Beach
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, (12)
"This is a very nice accommodation. Situated by the beautiful park and water. You can find shopping facilities within walking distance. The landlord was very reliable in making sure that our stay was very nice."
Spacious 3BR Private Home * Direct Water View
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, (3)
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, (1)
"The neighborhood is really nice and clean with a good variety of stores nearby. We found the subterranean haven to be a great location for unwinding and having small events. The George's are incredibly understanding, patient and flexible. We'd definitely recommend this host to anyone."
The price is HK$1,405
HK$1,608 total
includes taxes & fees
28 May - 29 May
The Subterranean Haven
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Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, (1)
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (1)
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is HK$3,893
HK$7,145 total
includes taxes & fees
19 May - 20 May
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Fridge, microwave, oven, stovetop
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
10.0 out of 10, Exceptional, (1)
"AAA++ for place and host"
The price is HK$1,240
HK$2,281 total
includes taxes & fees
21 May - 22 May
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
Exterior
COZY PRIVATE STUDIO w/ Free Off-Street Parking & Washer/Dryer
10.0 out of 10, Exceptional, (2)
"I came in town for an event I was doing and this property is always my first look. The location is Great to get on and off the highway/parkway pretty easily and it’s plenty to do near by. I’ll be back!!!"
COZY PRIVATE STUDIO w/ Free Off-Street Parking & Washer/Dryer
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Beach nearby, sun-loungers, beach towels
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Fridge, microwave, stovetop, coffee/tea maker
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, (3)
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is HK$1,171
HK$2,120 total
includes taxes & fees
31 May - 1 Jun
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Interior
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
10.0 out of 10, Exceptional, (4)
"We all slept well but beds do make lots of noise moving around on them. Bathrooms are clean and very nice."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Beach
The Safe House - High Tech Apt #2 - 3 Beds
10.0 out of 10, Exceptional, (29)
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The price is HK$921
HK$1,748 total
includes taxes & fees
22 May - 23 May
The Safe House - High Tech Apt #2 - 3 Beds
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is HK$1,435
HK$2,067 total
includes taxes & fees
20 May - 21 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (49)
"Beautiful location and old, well-maintained house. Really perfect for our family group of 17"
Waterfront Retreat Center for Health & Wellness
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Fridge, microwave, stovetop, coffee/tea maker
Modern And Quiet Getaway
9.6 out of 10, Exceptional, (20)
"We could not have been more pleased with our stay! The location was quiet and beautiful! Close enough to the City for sightseeing but far enough away to be quiet and relaxing. Our host was so easy to work with and was wonderful about responding to anything we needed."
Modern And Quiet Getaway
Smart TV
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
9.4 out of 10, Exceptional, (9)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Don't see what you're looking for?
See all available properties in Chappaqua
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.

Other types of properties in Chappaqua you may be interested in

Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, (1501)
"Pretty decent although an older property. Help very friendly. Breakfast included but they need better bagels."
The price is HK$780
HK$904 total
includes taxes & fees
20 May - 21 May
Amsterdam Hotel
Desk, laptop workspace, blackout curtains, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1005)
"Always clean. Good breakfast, rates are good"
The price is HK$1,028
HK$1,176 total
includes taxes & fees
26 May - 27 May
Baymont by Wyndham White Plains - Elmsford
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, (1473)
"I recommend this place. I stayed here after attending my best friend’s wedding nearby and I enjoyed it. Parking was complimentary, breakfast was really good and all the staff was amazingly friendly and professional. The room was big, everything was working fine: a/c and hot water. The bed was very comfortable. I definitely would stay here again. "
The price is HK$2,106
HK$2,568 total
includes taxes & fees
25 May - 26 May
Royal Regency Hotel
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.

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:

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

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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Chappaqua is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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. Jacob Burns Film Center Theater 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.

Recent reviews of Chappaqua properties
Expedia verified reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

5/5 Excellent
"Very pretty property and the rooms and pool were excellent!"
A verified traveller stayed at DoubleTree by Hilton Hotel Nanuet
Posted 2 days ago
DoubleTree by Hilton Hotel Nanuet