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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pleasantville holiday rentals

5 bedrooms

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 RM2,606
RM4,811 total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
In-room dining

2. 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 RM3,623
RM4,634 total
includes taxes & fees
1 Sept - 2 Sept
3BR Prime Luxury NY - Free Parking
Living area

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 RM906
RM1,636 total
includes taxes & fees
1 Sept - 2 Sept
Luxury NYC Home Game Room Free Parking
Dining

4. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is RM906
RM1,608 total
includes taxes & fees
7 Sept - 8 Sept
Prime Luxe 3-BR NYC - Free Parking
Private kitchen

5. 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 RM721
RM1,424 total
includes taxes & fees
1 Sept - 2 Sept
Elegant Hideaway with Free Parking
Dining

6. 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 RM906
RM1,729 total
includes taxes & fees
1 Sept - 2 Sept
Luxury NYC Home with Free Parking for 12
Exterior

7. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (170 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is RM660
RM759 total
includes taxes & fees
3 Sept - 4 Sept
Stamford Suites
Living area

8. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
5.6 out of 10, (4 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is RM815
RM1,512 total
includes taxes & fees
1 Sept - 2 Sept
Luxury 3BR Family Home Game Room Parking
Living area

9. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is RM3,441
RM4,450 total
includes taxes & fees
1 Sept - 2 Sept
Two Wash
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 RM809
RM1,505 total
includes taxes & fees
1 Sept - 2 Sept
Luxury 3 BR Near NYC with Easy Parking
Living area

11. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"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 RM906
RM1,653 total
includes taxes & fees
1 Sept - 2 Sept
Uscale 2BR Escape in the Heart of NYC
Living area

12. 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 RM2,355
RM3,234 total
includes taxes & fees
1 Sept - 2 Sept
Luxury 5 BR Home Free Parking
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)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is RM1,006
RM1,725 total
includes taxes & fees
1 Sept - 2 Sept
Modern Luxury Home w GameRoom & Parking
Living area

14. 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 RM1,264
RM2,014 total
includes taxes & fees
1 Sept - 2 Sept
Luxe 1BR Oasis - Prime NY Stay
Living area

15. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is RM906
RM1,613 total
includes taxes & fees
1 Sept - 2 Sept
Spacious 3BR Luxe Escape near NYC
Property entrance

16. 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 RM881
RM1,014 total
includes taxes & fees
1 Sept - 2 Sept
Guesthouse at Norwalk Inn
Living area

17. 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 RM1,300
RM2,055 total
includes taxes & fees
1 Sept - 2 Sept
Luxury 1BR located in Prime Yonkers Area
Living area

18. 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 RM906
RM1,613 total
includes taxes & fees
1 Sept - 2 Sept
Spacious 3BR Luxe Escape near NYC
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

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

8/10 Good
"Desayuno, clean room"
Jose 2-night trip
Posted 10 hours ago
Hyatt Place Fort Lee / George Washington Bridge

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
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  • 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.