Default HTG hotel image

Chappaqua Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chappaqua vacation rentals

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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ￥32,025
￥52,733 total
includes taxes & fees
Jul 28 - Jul 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is ￥34,297
￥115,347 total
includes taxes & fees
Jul 14 - Jul 15
3 Mi to Downtown: Spacious White Plains Home
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, (41 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥28,392
￥53,360 total
includes taxes & fees
Jul 5 - Jul 6
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥36,562
￥41,066 total
includes taxes & fees
Jul 22 - Jul 23
Harriman Outdoor Center - Mountain Laurel Cabin
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, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥34,799
￥65,257 total
includes taxes & fees
Jun 28 - Jun 29
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥36,401
￥68,204 total
includes taxes & fees
Jun 29 - Jun 30
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥20,223
￥62,922 total
includes taxes & fees
Jun 30 - Jul 1
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is ￥20,384
￥54,382 total
includes taxes & fees
Jun 29 - Jun 30
Stamford Hideaway w/ Fire Pit
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)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥23,296
￥50,410 total
includes taxes & fees
Jun 28 - Jun 29
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥36,401
￥68,464 total
includes taxes & fees
Jun 28 - Jun 29
Contemporary Cozy Cottage
In-room safe, iron/ironing board, travel crib, free WiFi

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is ￥65,521
￥120,584 total
includes taxes & fees
Jun 28 - Jun 29
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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, (3 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 ￥25,141
￥42,754 total
includes taxes & fees
Jul 22 - Jul 23
Cozy 1-bedroom retreat minutes from West Point!
Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is ￥50,815
￥116,598 total
includes taxes & fees
Jun 30 - Jul 1
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Interior

What's headline

What's headline
South Side
The price is ￥29,120
￥99,643 total
includes taxes & fees
Jun 28 - Jun 29
What's headline
Terrace/patio

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (7 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is ￥24,591
￥56,255 total
includes taxes & fees
Jul 14 - Jul 15
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Luxury House | Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is ￥72,783
￥105,524 total
includes taxes & fees
Jun 30 - Jul 1
Spacious 3BR Luxe Escape near NYC
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 ￥15,288
￥21,814 total
includes taxes & fees
Jun 28 - Jun 29
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Microwave, oven, stovetop

Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment
Carmel Hamlet
The price is ￥28,312
￥54,352 total
includes taxes & fees
Jul 4 - Jul 5
Serene 2-bedroom spacious apartment
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 ￥36,401
￥48,502 total
includes taxes & fees
Jun 29 - Jun 30
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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 ￥22,811
￥38,379 total
includes taxes & fees
Jul 7 - Jul 8
Piermont Oasis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chappaqua Hotel Reviews

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Overall great! Thank you"
Lisandra 1-night trip
Posted 2 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
  • Use the map to find apartments and other holiday homes in the Chappaqua neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chappaqua while they last

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

Frequently asked questions

Can I find a vacation rental in Chappaqua?

Yes, we offer vacation rentals in Chappaqua near Chappaqua Performing Arts Center, or you can select a more secluded option if you want a relaxing stay. Our travelers 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 vacation home rentals in Chappaqua?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Chappaqua is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Chappaqua?

Expedia has 3 vacation rentals for your stay in Chappaqua.

What’s there to see and do in Chappaqua?

Explore the area and family-friendly sights such as Westchester Skating Academy, 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 larger area.

What’s a vacation rental in Chappaqua like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chappaqua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.