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Chappaqua Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chappaqua vacation rentals

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.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,107 nightly
The price is $1,233
Sep 8 - Sep 9
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

2. 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.
$966 nightly
The price is $993
Sep 8 - Sep 9
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.

3. 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
$378 nightly
The price is $432
Sep 7 - Sep 8
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A room with two beds, white curtains, a ceiling light, and a window with a view.

4. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
$474 nightly
The price is $542
Sep 6 - Sep 7
Total with taxes and fees
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

5. '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.
$386 nightly
The price is $441
Sep 15 - Sep 16
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A covered area with exercise equipment, chairs, and a view through large windows.

6. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
$284 nightly
The price is $316
Sep 6 - Sep 7
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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.

7. '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.
$269 nightly
The price is $307
Sep 6 - Sep 7
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A campfire with a wooden table and benches by a lake.

8. 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)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
$331 nightly
The price is $374
Sep 20 - Sep 21
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

9. 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
$408 nightly
The price is $455
Sep 7 - Sep 8
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

10. 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, (11 reviews)
"Beautiful and restful"
United States
Lisa H.
$1,397 nightly
The price is $1,580
Sep 9 - Sep 10
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A modern kitchen with a large island, white cabinetry, stainless steel appliances, and a view through large windows.

11. 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.
$1,782 nightly
The price is $1,985
Sep 10 - Sep 11
Total with taxes and fees
Private Country Getaway
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

12. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$357 nightly
The price is $397
Sep 7 - Sep 8
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
A wooden staircase leading to a gazebo in a forested area with a metal railing.

13. 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.
$199 nightly
The price is $226
Sep 12 - Sep 13
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A modern kitchen with stainless steel appliances, a central island with chairs, and a window with a view.

14. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
$474 nightly
The price is $542
Sep 6 - Sep 7
Total with taxes and fees
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

15. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
$297 nightly
The price is $342
Sep 30 - Oct 1
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

16. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (170 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$154 nightly
The price is $178
Sep 6 - Sep 7
Total with taxes and fees
Stamford Suites
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

17. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
$345 nightly
The price is $395
Sep 6 - Sep 7
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A garden with a stone wall, a wooden fence, and a gravel path.

18. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
$200 nightly
The price is $223
Sep 22 - Sep 23
Total with taxes and fees
Piermont Oasis
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

19. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$365 nightly
The price is $414
Sep 5 - Sep 6
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A breakfast buffet with pastries, fruits, and a coffee station.

20. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
$1,025 nightly
The price is $1,141
Sep 7 - Sep 8
Total with taxes and fees
3BR Prime Luxury NY - Free Parking
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

Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

8/10 Good
"The breakfast was a nice option. The hotel is located close to buses....that can get you to the trains. Hotel was quiet"
Jackie 4-night trip
Posted 1 hour ago
Ramada by Wyndham Bronx

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chappaqua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental near Chappaqua is located next to a golf course and has a balcony, a barbecue grill, 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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.