Chappaqua Holiday Rentals from €152: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chappaqua has to offer?

Modern Luxury Home w GameRoom & Parking : This holiday home rental outside Chappaqua 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 that you can cook with friends or family.

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Our top choices for Chappaqua holiday rentals

A stone staircase leading to a house with a stone wall and a metal gate.

1. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson

Eva C.

includes taxes & fees

11 Nov - 12 Nov

A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

2. 1 Queen Bed | Smoking

Elmsford

Anonymous traveller

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!

Ossining

Karen O.

includes taxes & fees

9 Nov - 10 Nov

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

Ossining

includes taxes & fees

9 Nov - 10 Nov

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

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

CROTON HDSN

Margaret S.

A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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

Croton-on-Hudson

Mateo A.

A covered area with exercise equipment, chairs, and a view through large windows.

7. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

includes taxes & fees

15 Nov - 16 Nov

8. 1 King Bed | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

10 Nov - 11 Nov

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

9. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

includes taxes & fees

14 Nov - 15 Nov

A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

10. 2 Full Beds | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

8 Nov - 9 Nov

11. 1 Queen Bed | Non-Smoking

Elmsford

includes taxes & fees

10 Nov - 11 Nov

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

12. Stamford Suites

Downtown Stamford

Christine

includes taxes & fees

17 Nov - 18 Nov

A forested area with a bench and a fire pit.

13. Historic, private riverfront cottage in peaceful Greenwich

Greenwich

includes taxes & fees

7 Dec - 8 Dec

A garden with a stone wall, a wooden fence, and a gravel path.

14. Piermont Oasis

Piermont

Megan D.

includes taxes & fees

7 Dec - 8 Dec

15. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Downtown Stamford

Marisa C.

includes taxes & fees

10 Nov - 11 Nov

16. Polished 1BR w/ Accessible Room Features + Sauna

Ossining

"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "

Nada S.

includes taxes & fees

7 Dec - 8 Dec

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

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

Southeast Yonkers

Jordan S.

includes taxes & fees

8 Nov - 9 Nov

A wooden staircase leading to a gazebo in a forested area with a metal railing.

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

Greenwich

"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...

Kathleen W.

includes taxes & fees

7 Nov - 8 Nov

A modern living room with a sofa, a coffee table, and a bar stool.

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

Downtown Stamford

michelle b.

includes taxes & fees

20 Nov - 21 Nov

A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

20. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

includes taxes & fees

8 Nov - 9 Nov

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Find holiday rentals that suit your style

Top Chappaqua Hotel Reviews

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

Hotel MTK Mount Kisco

Mount Kisco

8/10 Good

We had arranged and prepaid for our family to stay at the hotel to be near relatives. The hotel was fine but the breakfast arrangement was not. Our family was harassed by one of the waitresses during the "free" breakfast for not tipping her enough for the beverages (which weren't free??). The whole situation left us feeling less than pleased with the hotel experience. Nor did management seem to take an active role in fixing the matter. I have never experienced anything like this at any...

Anonymous traveller

A modern hotel entrance with a glass door, a car parked outside, and a well-lit pathway leading to the entrance.

The Opus Westchester, Autograph Collection

White Plains

10/10 Excellent

Nancy

Find out more about Chappaqua

Everything you need to know about Chappaqua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaqua holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaqua holiday rentals we have selected for you start as low as €152 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 holiday 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 holiday.

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.

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?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Chappaqua 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 that you can cook with friends or family.

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 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.

Holiday Rentals in Chappaqua

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chappaqua holiday rentals

1. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

2. 1 Queen Bed | Smoking

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

4. Summer Pool Oasis Custom Bar Arcade Pool Table

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

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

7. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

8. 1 King Bed | Non-Smoking

9. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

10. 2 Full Beds | Non-Smoking

11. 1 Queen Bed | Non-Smoking

12. Stamford Suites

13. Historic, private riverfront cottage in peaceful Greenwich

14. Piermont Oasis

15. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

16. Polished 1BR w/ Accessible Room Features + Sauna

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

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

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

20. Modern Luxe 1BR Apt in Downtown Stamford

Find holiday rentals that suit your style

Top Chappaqua Hotel Reviews

Hotel MTK Mount Kisco

8/10 Good

Find out more about Chappaqua

Chappaqua holiday rentals: An excellent choice for every season

How to find incredible deals on Chappaqua rentals

Frequently Asked Questions

Can I find a holiday rental in Chappaqua?

What are some of the best holiday rentals that Chappaqua has to offer?

How many holiday rentals will I find in Chappaqua?

What’s there to see and do in Chappaqua?

What’s a holiday rental in Chappaqua like?