Chappaqua Holiday Rentals

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Our top choices for Chappaqua holiday rentals

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,232
HK$2,567 total
includes taxes & fees
4 Mar - 5 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,303
HK$2,777 total
includes taxes & fees
4 Mar - 5 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,760
HK$3,266 total
includes taxes & fees
4 Mar - 5 Mar
Contemporary Cozy Cottage

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"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$731
HK$1,474 total
includes taxes & fees
16 Mar - 17 Mar
Cozy 1-bedroom retreat minutes from West Point!

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, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,119
HK$2,210 total
includes taxes & fees
9 Mar - 10 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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$859
HK$1,207 total
includes taxes & fees
4 Mar - 5 Mar
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

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, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,470
HK$2,336 total
includes taxes & fees
17 Mar - 18 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$1,556
HK$2,946 total
includes taxes & fees
10 Mar - 11 Mar
Luxury 3BR Home Game Room Free Parking

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,056
HK$2,179 total
includes taxes & fees
4 Mar - 5 Mar
Charming 1-bedroom apartment in Carmel with WiFi, AC

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is HK$1,127
HK$2,927 total
includes taxes & fees
4 Mar - 5 Mar
Seabreeze at the beach west beach Stamford ct.

Family Cottage with 4 King Beds and Fire Pit

Family Cottage with 4 King Beds and Fire Pit
Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is HK$1,612
HK$4,189 total
includes taxes & fees
25 Mar - 26 Mar
Family Cottage with 4 King Beds and Fire Pit

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$2,461 total
includes taxes & fees
8 Mar - 9 Mar
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

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, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$704
HK$2,152 total
includes taxes & fees
4 Mar - 5 Mar
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 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$1,721
HK$3,051 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (1 review)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is HK$2,730
HK$4,219 total
includes taxes & fees
15 Mar - 16 Mar
Luxury 3BR Family Home Game Room Parking

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.6 out of 10, Exceptional, (5 reviews)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is HK$876
HK$3,287 total
includes taxes & fees
4 Mar - 5 Mar
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is HK$2,808
HK$4,307 total
includes taxes & fees
10 Mar - 11 Mar
Luxury 1BR located in Prime Yonkers Area

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$626
HK$2,494 total
includes taxes & fees
4 Mar - 5 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is HK$1,170
HK$2,358 total
includes taxes & fees
17 Mar - 18 Mar
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$1,150
HK$2,946 total
includes taxes & fees
4 Mar - 5 Mar
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

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:

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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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of 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 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 Westchester Skating Academy, or get out into nature at a spot like Hardscrabble Wilderness Area. Thomas J. Watson Research Center and Rockefeller State Park Preserve 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.