Short-Term Rentals in Chappaqua, NY: Compare 10+ Sites & Save

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36 Best Short-Term Rentals in Chappaqua (Starting from $146)

Ossining Vacation Rental Near River, Trails and MTA!
Ossining Vacation Rental Near River, Trails and MTA!
House
Ossining, NY, USA
5.2k from Chappaqua center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms11 Guests
9.5

Superb

2 reviews

$600
Average price / night
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Family home in one of NY top-ranked school districts with Tennis court
Family home in one of NY top-ranked school districts with Tennis court
House
Chappaqua, NY, 10514, United States
1.7k from Chappaqua center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$673
Average price / night
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Hudson River Views Firepit Patio Dog Run Game Room Stone Manor
Hudson River Views Firepit Patio Dog Run Game Room Stone Manor
House
Briarcliff Manor, NY, USA
9.6k from Chappaqua center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1160
Average price / night
Check Availability
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
Charming 3-bedroom house in enchanting Chappaqua with WiFi, AC and Sanctuary.
House
Chappaqua, NY, 10514, United States
2.0k from Chappaqua center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
9.2

Superb

5 reviews

$481
Average price / night
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Hudson River Views Briarcliff Manor Home with Deck
Hudson River Views Briarcliff Manor Home with Deck
House
Briarcliff Manor, NY, USA
9.6k from Chappaqua center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom12 Guests
10.0

Exceptional

2 reviews

$1143
Average price / night
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The Best of Both Worlds: For nature lovers but close to New York City.
The Best of Both Worlds: For nature lovers but close to New York City.
House
Chappaqua, NY, 10514, United States
2.0k from Chappaqua center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$680
Average price / night
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Contemporary 3 Bedroom Apt with Sauna in Woods
Contemporary 3 Bedroom Apt with Sauna in Woods
Apartment
Chappaqua, New York, USA
9.9k from Chappaqua center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$146
Average price / night
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Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
House
Mount Kisco, NY, 10549, United States
4.1k from Chappaqua center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
7.4

Good

3 reviews

$721
Average price / night
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Croton Quarters - Comfortable Apartments, NYC close
Croton Quarters - Comfortable Apartments, NYC close
Apartment
Croton-on-Hudson, NY, USA
10.0k from Chappaqua center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$283
Average price / night
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Tranquil Country Contemporary
Tranquil Country Contemporary
House
Mt Kisco, NY, 10549, United States
4.2k from Chappaqua center

Internet, Kitchen, No Smoking

3 Bedrooms6 Guests
New to Booking
$646
Average price / night
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Beautiful apartment 1 in great Pleasantville, NY
Beautiful apartment 1 in great Pleasantville, NY
Apartment
Pleasantville, NY, 10570, United States
4.6k from Chappaqua center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$350
Average price / night
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Beautiful Apt 2 in Pleasantville, Westchester, NY
Beautiful Apt 2 in Pleasantville, Westchester, NY
Apartment
Pleasantville, NY, 10570, United States
5.0k from Chappaqua center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$243
Average price / night
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NEW! Cozy Pleasantville Retreat Unit 2
NEW! Cozy Pleasantville Retreat Unit 2
Apartment
Pleasantville, NY, 10570, United States
5.0k from Chappaqua center

AC, Free Parking, Heater, Internet, Microwave, No Smoking, Patio, TV

2 Bedrooms4 Guests
New to Booking
$362
Average price / night
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Pet Friendly | Parks & Trails | Pleasantville Home
Pet Friendly | Parks & Trails | Pleasantville Home
Apartment
Pleasantville, NY, 10570, United States
5.0k from Chappaqua center

AC, Dryer, Free Parking, Heater, Internet, Microwave, No Smoking, Patio, TV

3 Bedrooms4 Guests
New to Booking
$453
Average price / night
Check Availability
Clean, Comfy & Convenient 1 Bed Apt in the Village
Clean, Comfy & Convenient 1 Bed Apt in the Village
Apartment
Mount Kisco, NY, 10549, United States
5.0k from Chappaqua center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom3 Guests
10.0

Exceptional

3 reviews

$191
Average price / night
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NYC-Area Escape Near River, Trails & MTA!
NYC-Area Escape Near River, Trails & MTA!
House
Ossining, NY, 10562, United States
5.2k from Chappaqua center

AC, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Kitchen

5 Bedrooms11 Guests
8.2

Very Good

15 reviews

$713
Average price / night
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Beautiful Brand New  Private Duplex Unit in  Lower Hudson Valley  \"Stone Haven\"
Beautiful Brand New Private Duplex Unit in Lower Hudson Valley \"Stone Haven\"
House
Briarcliff Manor, NY, 10510, United States
5.5k from Chappaqua center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom5 Guests
10.0

Exceptional

12 reviews

$389
Average price / night
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Serene Retreat in the Hills of Westchester
Serene Retreat in the Hills of Westchester
House
Mount Kisco, NY, 10549, United States
5.6k from Chappaqua center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry

4 Bedrooms8 Guests
New to Booking
$635
Average price / night
Check Availability
2BDRM COTTAGE IN PLEASANTVILLE
2BDRM COTTAGE IN PLEASANTVILLE
Cottage
Pleasantville, NY, 10570, United States
6.1k from Chappaqua center

AC, Dryer, Heater, Laundry, No Smoking, Washer

2 Bedrooms2 Guests
New to Booking
$3564
Average price / night
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8500sqft Brick House close to MRT Train and Westchester Airport
8500sqft Brick House close to MRT Train and Westchester Airport
House
Thornwood, NY, 10594, United States
6.2k from Chappaqua center

Hot Tub, No Smoking

5 Bedrooms12 Guests
New to Booking
$1708
Average price / night
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Luxury 8 BR Estate with Pool and Tennis court
Luxury 8 BR Estate with Pool and Tennis court
House
Mount Kisco, NY, 10549, United States
7.2k from Chappaqua center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

8 Bedrooms16 Guests
10.0

Exceptional

26 reviews

$3001
Average price / night
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Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House
Ossining, NY, 10562, United States
7.4k from Chappaqua center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms13 Guests
9.2

Superb

7 reviews

$868
Average price / night
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Neighbor's house - Welcome!
Neighbor's house - Welcome!
House
Ossining, NY, 10562, United States
7.5k from Chappaqua center

AC, Arcade, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$197
Average price / night
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Polished 1BR w/ Accessible Room Features + Sauna
Polished 1BR w/ Accessible Room Features + Sauna
Apartment
Ossining, NY, 10562, United States
8.0k from Chappaqua center

AC, Free Parking, Heater, Internet, No Smoking, Spa, Tennis Court, Toys, TV

1 Bedroom2 Guests
6.0

Review score

1 reviews

$358
Average price / night
Check Availability
Designer Home in Lower Hudson Valley
Designer Home in Lower Hudson Valley
House
Yorktown Heights, NY, 10598, United States
8.1k from Chappaqua center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1152
Average price / night
Check Availability
Willoway: family-friendly retreat, Pool, 3+ wooded acres
Willoway: family-friendly retreat, Pool, 3+ wooded acres
House
Ossining, NY, 10562, United States
8.2k from Chappaqua center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$441
Average price / night
Check Availability
1BR Queen near NYC | Trails, Biking & Sauna Bliss
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Apartment
Ossining, NY, 10562, United States
8.3k from Chappaqua center

AC, Free Parking, Heater, Internet, No Smoking, Spa, Tennis Court, Toys, TV

1 Bedroom2 Guests
New to Booking
$332
Average price / night
Check Availability

Other accommodation types in Chappaqua:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Chappaqua.

Chappaqua Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 36 verified short-term rentals in Chappaqua, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chappaqua vary depending on location, property size, and travel dates. Rates typically start from around $146 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chappaqua include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chappaqua, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chappaqua often include amenities such as Fireplace/Heating, Bedding/Linens, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Chappaqua are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.