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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chappaqua vacation rentals

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

1. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
The price is CA $378
CA $1,128 total
includes taxes & fees
Sep 15 - Sep 16
Nyc-area Escape Near River, Trails & Mta!
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

2. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is CA $304
CA $1,157 total
includes taxes & fees
Sep 15 - Sep 16
NYC-Area Escape Near River, Trails & MTA!
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

3. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is CA $706
CA $1,401 total
includes taxes & fees
Sep 14 - Sep 15
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is CA $914
CA $1,711 total
includes taxes & fees
Sep 14 - Sep 15
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

5. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is CA $685
CA $990 total
includes taxes & fees
Sep 27 - Sep 28
Luxury NYC Home Game Room Free Parking
A parking lot with multiple cars, a building with red awnings, and trees in the background.

6. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
The price is CA $173
CA $198 total
includes taxes & fees
Sep 13 - Sep 14
1 Queen Bed | Non-Smoking
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

7. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is CA $256
CA $520 total
includes taxes & fees
Sep 14 - Sep 15
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

8. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is CA $374
CA $756 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

9. '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 CA $198
CA $408 total
includes taxes & fees
Sep 14 - Sep 15
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

10. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is CA $265
CA $515 total
includes taxes & fees
Oct 4 - Oct 5
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

11. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is CA $248
CA $490 total
includes taxes & fees
Sep 27 - Sep 28
Elegant Hideaway with Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

12. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is CA $560
CA $872 total
includes taxes & fees
Sep 17 - Sep 18
Luxury NYC Home with Free Parking for 12
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view through large windows.

13. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is CA $1,799
CA $2,866 total
includes taxes & fees
Sep 21 - Sep 22
Private Country Getaway
A campfire with a wooden table and benches by a lake.

14. 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, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is CA $264
CA $485 total
includes taxes & fees
Oct 4 - Oct 5
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A covered area with exercise equipment, chairs, and a view through large windows.

15. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is CA $345
CA $431 total
includes taxes & fees
Sep 27 - Sep 28
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A parking lot with multiple cars, a building with red awnings, and trees in the background.

16. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
The price is CA $178
CA $203 total
includes taxes & fees
Sep 27 - Sep 28
1 King Bed | Non-Smoking
A parking lot with multiple cars, a building with red awnings, and trees in the background.

17. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
The price is CA $182
CA $208 total
includes taxes & fees
Sep 13 - Sep 14
2 Full Beds | Non-Smoking
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

18. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is CA $1,090
CA $2,175 total
includes taxes & fees
Sep 27 - Sep 28
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

19. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is CA $747
CA $1,038 total
includes taxes & fees
Sep 13 - Sep 14
Prime Luxe 3-BR NYC - Free Parking
A wooden staircase leading to a gazebo in a forested area with a metal railing.

20. 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
8.0 out of 10, Very good, (5 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 CA $234
CA $311 total
includes taxes & fees
Sep 27 - Sep 28
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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

Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"Nnnnxxxxxxxxxxxx. Xxxxxxxxxx"
Garry 3-night trip
Posted less than an hour ago
Sonesta White Plains Downtown

Find out more about Chappaqua

Everything you need to know about Chappaqua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaqua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chappaqua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaqua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chappaqua vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaqua vacation rentals we have selected for you start as low as CA $254 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chappaqua rentals

At Expedia, we put the best Chappaqua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chappaqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaqua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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?

Modern Luxury Home w GameRoom & Parking: Located near Chappaqua, this vacation home rental is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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 Bruce Museum of Arts and Science, or get out into nature at a spot like Hardscrabble Wilderness Area. Chappaqua Performing Arts Center and Rockefeller State Park Preserve 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.