Chappaqua Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Chappaqua holiday rentals

TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$863
HK$1,625 total
includes taxes & fees
12 May - 13 May
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$940
HK$1,631 total
includes taxes & fees
18 May - 19 May
Piermont Oasis
TV, fireplace

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

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,585
HK$3,084 total
includes taxes & fees
11 May - 12 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,305
HK$3,807 total
includes taxes & fees
11 May - 12 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (13 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,441
HK$2,878 total
includes taxes & fees
25 May - 26 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (34 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,339
HK$2,511 total
includes taxes & fees
21 May - 22 May
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is HK$2,325
HK$6,153 total
includes taxes & fees
12 May - 13 May
New Beach Home near Stamford Downtown/Shippan
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (136 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,472
HK$2,488 total
includes taxes & fees
11 May - 12 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is HK$1,127
HK$2,440 total
includes taxes & fees
11 May - 12 May
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is HK$900
HK$2,403 total
includes taxes & fees
11 May - 12 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$1,010
HK$3,081 total
includes taxes & fees
11 May - 12 May
House on the Babbling Brook- Quiet 2BR + King Bed!
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is HK$1,793
HK$3,181 total
includes taxes & fees
11 May - 12 May
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Fridge, microwave, oven, stovetop

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is HK$861
HK$2,633 total
includes taxes & fees
17 May - 18 May
Modern 1BR Apt / Free Parking / Near NYC
Terrace/patio

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

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is HK$740
HK$1,056 total
includes taxes & fees
15 May - 16 May
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,722
HK$3,233 total
includes taxes & fees
11 May - 12 May
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
TV, books, stereo

Stylish Studio Minutes to Train U5

Stylish Studio Minutes to Train U5
Glenbrook-Belltown
Stylish Studio Minutes to Train U5
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$1,104
HK$3,552 total
includes taxes & fees
11 May - 12 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is HK$1,558
HK$1,866 total
includes taxes & fees
11 May - 12 May
Luxury home near West Point
Property grounds

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$1,325
HK$1,767 total
includes taxes & fees
11 May - 12 May
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is HK$1,566
HK$2,541 total
includes taxes & fees
11 May - 12 May
Luxury House Near West Point
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

Royal Regency Hotel

Royal Regency Hotel

8/10 Good
"Nice place to stay"
sydjea 1-night trip
Posted 3 hours ago
Royal Regency Hotel

Find out more about Chappaqua

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:

  • View our selection of featured holiday rentals in Chappaqua
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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 in Chappaqua close to Chappaqua Performing Arts Center, 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Chappaqua is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

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. Chappaqua Performing Arts Center and Jacob Burns Film Center Theater 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.