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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Pleasantville vacation rentals

Property grounds

1. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
The price is SAR 446
SAR 510 total
includes taxes & fees
23 Sep - 24 Sep
1 Queen Bed | Smoking
Desk, WiFi (free), bed sheets

2. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
The price is SAR 559
SAR 1,129 total
includes taxes & fees
24 Sep - 25 Sep
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds

3. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is SAR 451
SAR 791 total
includes taxes & fees
29 Sep - 30 Sep
Piermont Oasis
Property grounds

4. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is SAR 939
SAR 1,525 total
includes taxes & fees
25 Sep - 26 Sep
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Property grounds

5. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
The price is SAR 506
SAR 579 total
includes taxes & fees
22 Oct - 23 Oct
1 Queen Bed | Non-Smoking
Property grounds

6. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
The price is SAR 457
SAR 523 total
includes taxes & fees
23 Sep - 24 Sep
1 King Bed | Non-Smoking
Property grounds

7. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
The price is SAR 469
SAR 536 total
includes taxes & fees
23 Sep - 24 Sep
2 Full Beds | Non-Smoking
Smart TV, video games, DVD player, books

8. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (8 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is SAR 807
SAR 1,541 total
includes taxes & fees
24 Sep - 25 Sep
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Property grounds

9. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is SAR 636
SAR 848 total
includes taxes & fees
25 Sep - 26 Sep
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Dining

10. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is SAR 717
SAR 1,408 total
includes taxes & fees
4 Oct - 5 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Property grounds

11. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is SAR 714
SAR 1,305 total
includes taxes & fees
11 Oct - 12 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
3 bedrooms, iron/ironing board, internet, bed sheets

12. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
The price is SAR 1,014
SAR 2,036 total
includes taxes & fees
23 Sep - 24 Sep
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Living area

13. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is SAR 1,014
SAR 2,062 total
includes taxes & fees
23 Sep - 24 Sep
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
House | 5 bedrooms

14. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is SAR 2,475
SAR 4,633 total
includes taxes & fees
23 Sep - 24 Sep
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

15. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is SAR 1,916
SAR 3,744 total
includes taxes & fees
23 Sep - 24 Sep
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Private kitchen

16. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is SAR 1,014
SAR 2,036 total
includes taxes & fees
23 Sep - 24 Sep
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
TV

17. Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC

Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
Dunwoodie
The price is SAR 490
SAR 803 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
1 bedroom, iron/ironing board, WiFi (free), bed sheets

18. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is SAR 355
SAR 506 total
includes taxes & fees
27 Sep - 28 Sep
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Villa, Garden View | Living area

19. 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 SAR 1,859
SAR 2,686 total
includes taxes & fees
27 Sep - 28 Sep
Luxury NYC Home Game Room Free Parking
Terrace/patio

20. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (11 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is SAR 470
SAR 1,519 total
includes taxes & fees
30 Sep - 1 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
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

Royal Regency Hotel

Royal Regency Hotel

8/10 Good
"It was clean and the complimentary breakfast was excellent."
Rahima 1-night trip
Posted 8 hours ago
Royal Regency Hotel

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

Modern Luxury Home w GameRoom & Parking: This vacation 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 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 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.