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

Search Holiday Rentals in Pleasantville

  • 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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pleasantville holiday rentals

Villa, Garden View | Living area

1. 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 ฿7,390
฿13,347 total
includes taxes & fees
23 Aug - 24 Aug
Luxury NYC Home Game Room Free Parking
Luxury Apartment | Private kitchen

2. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is ฿5,883
฿11,622 total
includes taxes & fees
28 Aug - 29 Aug
Elegant Hideaway with Free Parking
Apartment (1 Bedroom) | Interior

3. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is ฿5,621
฿10,626 total
includes taxes & fees
15 Sept - 16 Sept
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury Villa, Garden View | Dining

4. 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 ฿7,390
฿14,110 total
includes taxes & fees
23 Aug - 24 Aug
Luxury NYC Home with Free Parking for 12
Exterior

5. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (162 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is ฿4,418
฿5,081 total
includes taxes & fees
30 Aug - 31 Aug
Stamford Suites
Dining

6. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ฿7,390
฿13,125 total
includes taxes & fees
30 Aug - 31 Aug
Prime Luxe 3-BR NYC - Free Parking
Standard Room, 1 King Bed, Main Building | Property entrance

7. 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 ฿7,193
฿8,272 total
includes taxes & fees
23 Aug - 24 Aug
Guesthouse at Norwalk Inn
House | 5 bedrooms

8. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ฿23,059
฿41,263 total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Luxury Apartment | Living area

9. NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ฿3,577
฿8,896 total
includes taxes & fees
24 Aug - 25 Aug
NY Luxury Apt Free Parking in PRIME Area
Luxury Apartment | Living area

10. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is ฿6,606
฿12,284 total
includes taxes & fees
24 Aug - 25 Aug
Luxury 3 BR Near NYC with Easy Parking
Luxury House | Living area

11. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is ฿7,390
฿13,162 total
includes taxes & fees
24 Aug - 25 Aug
Spacious 3BR Luxe Escape near NYC
Luxury Duplex | Living area

12. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is ฿7,390
฿13,490 total
includes taxes & fees
22 Aug - 23 Aug
Uscale 2BR Escape in the Heart of NYC
House | Living area

13. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.6 out of 10, (11 reviews)
"The property that I paid for 1st, they told me that the pipe busted after I paid the cleaning fee. I paid for a property to sleep 6 people so 1 person had to sleep on the floor & another person had to sleep on a broken futon couch. The bed I was sleeping on was broken & there was pee stains on sheet & blanket. I asked them for a discount because of the unexpected things my family went through & they stopped communicating with me until the next day. But do not get any property rental from these...
United States
Ronnie
The price is ฿8,212
฿14,081 total
includes taxes & fees
23 Aug - 24 Aug
Modern Luxury Home w GameRoom & Parking
Luxury House, Garden View | Living area

14. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is ฿6,651
฿12,335 total
includes taxes & fees
23 Aug - 24 Aug
Luxury 3BR Family Home Game Room Parking
Luxury House | Living area

15. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
The price is ฿7,390
฿13,162 total
includes taxes & fees
24 Aug - 25 Aug
Spacious 3BR Luxe Escape near NYC
Luxury Apartment | In-room dining

16. 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 ฿29,561
฿37,818 total
includes taxes & fees
28 Aug - 29 Aug
3BR Prime Luxury NY - Free Parking
Luxury Apartment | Living area

17. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
The price is ฿10,317
฿16,436 total
includes taxes & fees
27 Aug - 28 Aug
Luxe 1BR Oasis - Prime NY Stay
Luxury Apartment | Living area

18. Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is ฿10,613
฿16,767 total
includes taxes & fees
27 Aug - 28 Aug
Luxury 1BR located in Prime Yonkers Area
Luxury Villa, Patio | Living area

19. 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 ฿19,215
฿26,391 total
includes taxes & fees
25 Aug - 26 Aug
Luxury 5 BR Home Free Parking
Luxury House | Living area

20. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is ฿28,083
฿36,312 total
includes taxes & fees
22 Aug - 23 Aug
Two Wash
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

Homewood Suites by Hilton Teaneck Glenpointe

Homewood Suites by Hilton Teaneck Glenpointe

10/10 Excellent
"Very clean 👌"
joseph 3-night trip
Posted 11 hours ago
Homewood Suites by Hilton Teaneck Glenpointe

Find out more about Pleasantville

Search for holiday rentals in Pleasantville on Expedia! 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 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’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.