A calm lake surrounded by autumn-colored trees reflecting in the water.

Pleasantville Holiday Rentals

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Our top choices for Pleasantville holiday rentals

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is S$1,574
includes taxes & fees
21 Sept - 22 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table

2. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is S$958
includes taxes & fees
21 Sept - 22 Sept
Prime Luxe 3-BR NYC - Free Parking

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
The price is S$913
includes taxes & fees
27 Sept - 28 Sept
Luxury NYC Home Game Room Free Parking

4. 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
The price is S$1,469
includes taxes & fees
21 Sept - 22 Sept
3BR Prime Luxury NY - Free Parking

5. 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 S$804
includes taxes & fees
24 Sept - 25 Sept
Luxury NYC Home with Free Parking for 12

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (179 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is S$248
includes taxes & fees
27 Sept - 28 Sept
Stamford Suites

7. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
The price is S$1,025
includes taxes & fees
22 Sept - 23 Sept
Luxury 5 BR Home 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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Frequently asked questions

Can I find a holiday rental in Pleasantville?

Yes, there are holiday rentals in Pleasantville close to Jacob Burns Film Center Media Arts Lab, or you can select a more secluded option if you're looking for a relaxing stay. Pleasantville is known for its restaurants and sporting events.

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

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Pleasantville 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.

What’s there to see and do in Pleasantville?

Cultural attractions include Jacob Burns Film Center Theater, whereas Rockefeller State Park Preserve is a spot to enjoy nature. In the wider area, you’ll find Jacob Burns Film Center Media Arts Lab and New York Medical College.

What’s a holiday rental in Pleasantville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pleasantville. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.