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

Pleasantville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pleasantville holiday rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
Snow Days & City Escapes: Spacious Ossining Home
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.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is RM2,092
RM4,265 total
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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
The price is RM2,020
RM2,919 total
includes taxes & fees
19 Oct - 20 Oct
Luxury NYC Home Game Room Free Parking
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

4. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (195 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is RM669
RM770 total
includes taxes & fees
22 Oct - 23 Oct
Stamford Suites
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
The price is RM1,653
RM2,572 total
includes taxes & fees
19 Oct - 20 Oct
Luxury NYC Home with Free Parking for 12
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

6. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is RM1,465
RM1,685 total
includes taxes & fees
19 Oct - 20 Oct
Guesthouse at Norwalk Inn
A breakfast buffet with pastries, fruits, and a coffee station.

7. 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 RM3,673
RM4,699 total
includes taxes & fees
19 Oct - 20 Oct
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

8. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is RM3,490
RM4,495 total
includes taxes & fees
19 Oct - 20 Oct
Prime Luxe 3-BR NYC - 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasantville Hotel Reviews

Hampton Inn & Suites Teaneck Glenpointe

Hampton Inn & Suites Teaneck Glenpointe

10/10 Excellent
"Great"
Juan 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Teaneck Glenpointe

Find out more about Pleasantville

Search for holiday rentals in Pleasantville on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Pleasantville using one of the methods below:

  • View our selection of featured holiday rentals in Pleasantville
  • Use the map to find apartments and other holiday homes in the Pleasantville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pleasantville while they last

Look no further and take a look at our great range of rental properties in Pleasantville!

Frequently asked questions

Can I find a holiday rental in Pleasantville?

Yes, there are holiday rentals in Pleasantville close to Jacob Burns Film Center Theater, 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 of 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.