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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Short-Term Rentals
  3.  USA

  4.  New York

  5.  White Plains
  6.  Pleasantville

Refine your search

Price per night

Amenity Filter

Rating

57 Best Short-Term Rentals in Pleasantville (Starting from $104)

Ossining Vacation Rental Near River, Trails and MTA!
Ossining Vacation Rental Near River, Trails and MTA!
House
Ossining, NY, USA
6.0k from Pleasantville 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
Check Availability
NEW! Cozy Pleasantville Retreat Unit 2
NEW! Cozy Pleasantville Retreat Unit 2
Apartment
Pleasantville, NY, 10570, United States
0.7k from Pleasantville center

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

2 Bedrooms4 Guests
New to Booking
$362
Average price / night
Check Availability
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
6.1k from Pleasantville 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
Pet Friendly | Parks & Trails | Pleasantville Home
Pet Friendly | Parks & Trails | Pleasantville Home
Apartment
Pleasantville, NY, 10570, United States
0.7k from Pleasantville center

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

3 Bedrooms4 Guests
New to Booking
$453
Average price / night
Check Availability
Hudson River Views Briarcliff Manor Home with Deck
Hudson River Views Briarcliff Manor Home with Deck
House
Briarcliff Manor, NY, USA
6.1k from Pleasantville 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
Check Availability
Beautiful apartment 1 in great Pleasantville, NY
Beautiful apartment 1 in great Pleasantville, NY
Apartment
Pleasantville, NY, 10570, United States
0.9k from Pleasantville center

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

3 Bedrooms6 Guests
New to Booking
$350
Average price / night
Check Availability
Luxury NY Home with Game Room and Free Parking
Luxury NY Home with Game Room and Free Parking
House
White Plains, NY, USA
7.8k from Pleasantville center

Security/Safety, Internet, Parking, Air Conditioner, Child Friendly

1 Bedroom7 Guests
New to Booking
$359
Average price / night
Check Availability
Beautiful Apt 2 in Pleasantville, Westchester, NY
Beautiful Apt 2 in Pleasantville, Westchester, NY
Apartment
Pleasantville, NY, 10570, United States
1.1k from Pleasantville center

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

2 Bedrooms4 Guests
New to Booking
$243
Average price / night
Check Availability
3 Mi to Downtown Spacious White Plains Home
3 Mi to Downtown Spacious White Plains Home
House
White Plains, NY, USA
8.3k from Pleasantville center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms12 Guests
7.3

Good

3 reviews

$768
Average price / night
Check Availability
2BDRM COTTAGE IN PLEASANTVILLE
2BDRM COTTAGE IN PLEASANTVILLE
Cottage
Pleasantville, NY, 10570, United States
1.2k from Pleasantville center

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

2 Bedrooms2 Guests
New to Booking
$3564
Average price / night
Check Availability
Cozy Homeva Kensico WP
Cozy Homeva Kensico WP
House
White Plains, NY, USA
9.3k from Pleasantville center

Kitchen, View, Parking, Laundry, Internet, Balcony/Terrace, Entertainment

4 Bedrooms8 Guests
New to Booking
$104
Average price / night
Check Availability
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
2.9k from Pleasantville center

Hot Tub, No Smoking

5 Bedrooms12 Guests
New to Booking
$1708
Average price / night
Check Availability
American Room At Cozy Homeva
American Room At Cozy Homeva
House
White Plains, NY, USA
9.3k from Pleasantville center

Parking, Laundry, Fireplace/Heating, Air Conditioner, Entertainment, Kitchen, Balcony/Terrace

1 Bedroom2 Guests
New to Booking
$104
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
3.8k from Pleasantville center

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

3 Bedrooms5 Guests
9.2

Superb

5 reviews

$481
Average price / night
Check Availability
Luxury Designer Home near NYC with Free Parking
Luxury Designer Home near NYC with Free Parking
House
White Plains, NY, USA
10.0k from Pleasantville center

Air Conditioner, Internet, Security/Safety, Parking, Child Friendly

1 Bedroom12 Guests
New to Booking
$498
Average price / night
Check Availability
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
3.9k from Pleasantville center

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

4 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$680
Average price / night
Check Availability
Prime Luxury NY with Free Parking and Mins to Downtown!
Prime Luxury NY with Free Parking and Mins to Downtown!
House
White Plains, NY, USA
10.0k from Pleasantville center

Air Conditioner, Internet, Security/Safety, Parking, Child Friendly

1 Bedroom16 Guests
New to Booking
$498
Average price / night
Check Availability
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
3.9k from Pleasantville center

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

4 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$673
Average price / night
Check Availability
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
5.2k from Pleasantville center

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

1 Bedroom5 Guests
10.0

Exceptional

12 reviews

$389
Average price / night
Check Availability
NYC-Area Escape Near River, Trails & MTA!
NYC-Area Escape Near River, Trails & MTA!
House
Ossining, NY, 10562, United States
6.0k from Pleasantville 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
Check Availability
Hudson River Views: Briarcliff Manor Home w/ Deck
Hudson River Views: Briarcliff Manor Home w/ Deck
House
Briarcliff Manor, NY, 10510-2404, United States
6.1k from Pleasantville center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms12 Guests
9.8

Exceptional

14 reviews

$1295
Average price / night
Check Availability
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House
Ossining, NY, 10562, United States
6.3k from Pleasantville center

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

5 Bedrooms13 Guests
9.2

Superb

7 reviews

$868
Average price / night
Check Availability
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
House
Mount Kisco, NY, 10549, United States
6.3k from Pleasantville center

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

4 Bedrooms8 Guests
7.4

Good

3 reviews

$721
Average price / night
Check Availability
Cozy house on the Hudson
Cozy house on the Hudson
House
Ossining, NY, 10562, United States
6.3k from Pleasantville center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
9.6

Exceptional

73 reviews

$254
Average price / night
Check Availability
Neighbor's house - Welcome!
Neighbor's house - Welcome!
House
Ossining, NY, 10562, United States
6.7k from Pleasantville center

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

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$197
Average price / night
Check Availability
Tranquil Country Contemporary
Tranquil Country Contemporary
House
Mt Kisco, NY, 10549, United States
7.0k from Pleasantville center

Internet, Kitchen, No Smoking

3 Bedrooms6 Guests
New to Booking
$646
Average price / night
Check Availability
Luxury Urban Retreat + Spacious & Stylish
Luxury Urban Retreat + Spacious & Stylish
Apartment
White Plains, NY, 10603, United States
7.2k from Pleasantville center

AC, Heater, Laundry, No Smoking

3 Bedrooms6 Guests
New to Booking
$521
Average price / night
Check Availability

Other accommodation types in Pleasantville:

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 Pleasantville.

Pleasantville Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 57 verified short-term rentals in Pleasantville, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Pleasantville vary depending on location, property size, and travel dates. Rates typically start from around $104 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Pleasantville 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 Pleasantville, 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 Pleasantville often include amenities such as Fireplace/Heating, Laundry, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Pleasantville 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.