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

Pleasantville Vacation Rentals

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Check prices for these dates

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

Our top choices for Pleasantville vacation rentals

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 P13,903
P25,108 total
includes taxes & fees
Aug 23 - Aug 24
Luxury NYC Home Game Room Free Parking
Private kitchen

2. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is P11,066
P21,864 total
includes taxes & fees
Aug 21 - Aug 22
Elegant Hideaway with Free Parking
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 P8,774
P17,913 total
includes taxes & fees
Aug 24 - Aug 25
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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 P13,903
P26,544 total
includes taxes & fees
Aug 23 - Aug 24
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 P8,304
P9,550 total
includes taxes & fees
Aug 23 - Aug 24
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 P13,903
P24,690 total
includes taxes & fees
Aug 25 - Aug 26
Prime Luxe 3-BR NYC - Free Parking
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 P13,539
P15,569 total
includes taxes & fees
Aug 23 - Aug 24
Guesthouse at Norwalk Inn
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 P43,343
P77,562 total
includes taxes & fees
Sep 1 - Sep 2
Summer Pool Oasis Custom Bar Arcade Pool Table
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 P6,729
P16,734 total
includes taxes & fees
Aug 21 - Aug 22
NY Luxury Apt Free Parking in PRIME Area
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 P12,427
P23,109 total
includes taxes & fees
Aug 27 - Aug 28
Luxury 3 BR Near NYC with Easy Parking
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 P13,903
P24,760 total
includes taxes & fees
Aug 23 - Aug 24
Spacious 3BR Luxe Escape near NYC
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 P13,903
P25,378 total
includes taxes & fees
Aug 21 - Aug 22
Uscale 2BR Escape in the Heart of NYC
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 P15,447
P26,488 total
includes taxes & fees
Aug 23 - Aug 24
Modern Luxury Home w GameRoom & Parking
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 P12,512
P23,205 total
includes taxes & fees
Aug 23 - Aug 24
Luxury 3BR Family Home Game Room Parking
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 P13,903
P24,760 total
includes taxes & fees
Aug 23 - Aug 24
Spacious 3BR Luxe Escape near NYC
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 P55,610
P71,142 total
includes taxes & fees
Aug 25 - Aug 26
3BR Prime Luxury NY - Free Parking
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 P19,408
P30,919 total
includes taxes & fees
Aug 25 - Aug 26
Luxe 1BR Oasis - Prime NY Stay
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 P19,964
P31,541 total
includes taxes & fees
Aug 21 - Aug 22
Luxury 1BR located in Prime Yonkers Area
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 P36,147
P49,646 total
includes taxes & fees
Aug 21 - Aug 22
Luxury 5 BR Home Free Parking
Living area

20. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is P52,830
P68,310 total
includes taxes & fees
Aug 21 - Aug 22
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.
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Top Pleasantville Hotel Reviews

Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

10/10 Excellent
"Very friendly staff and the room is clean but parking is very tight it’s first come basis with the parking"
Maria 2-night trip
Posted 6 hours ago
Ramada by Wyndham Bronx

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:

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Frequently asked questions

Can I find a vacation rental in Pleasantville?

Yes, we give you a choice of vacation rentals in Pleasantville close to Jacob Burns Film Center Media Arts Lab, or you can select a more secluded option if you'd like a relaxing place to 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 larger area, you’ll find Jacob Burns Film Center Media Arts Lab and New York Medical College.

What’s a vacation rental in Pleasantville like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Pleasantville. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips.