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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pleasantville vacation rentals

A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

1. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveler
The price is ￥19,073
￥21,816 total
includes taxes & fees
Nov 29 - Nov 30
1 Queen Bed | Smoking
A stone staircase leading to a house with a stone wall and a metal gate.

2. 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, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is ￥39,973
￥64,556 total
includes taxes & fees
Nov 15 - Nov 16
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A garden with a stone wall, a wooden fence, and a gravel path.

3. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥19,187
￥32,055 total
includes taxes & fees
Nov 29 - Nov 30
Piermont Oasis
A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

4. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveler
The price is ￥19,996
￥22,872 total
includes taxes & fees
Nov 23 - Nov 24
2 Full Beds | Non-Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

5. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveler
The price is ￥19,534
￥22,343 total
includes taxes & fees
Nov 24 - Nov 25
1 King Bed | Non-Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

6. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
8.0 out of 10, Very good, (6 reviews)
The price is ￥19,073
￥21,816 total
includes taxes & fees
Nov 17 - Nov 18
1 Queen Bed | Non-Smoking
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

7. 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)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is ￥54,363
￥121,928 total
includes taxes & fees
Nov 16 - Nov 17
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

8. 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, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is ￥29,890
￥56,865 total
includes taxes & fees
Nov 18 - Nov 19
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ￥78,433
￥163,143 total
includes taxes & fees
Nov 16 - Nov 17
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

10. '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, (9 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 ￥35,906
￥64,841 total
includes taxes & fees
Nov 19 - Nov 20
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

11. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (210 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is ￥20,946
￥24,088 total
includes taxes & fees
Nov 22 - Nov 23
Stamford Suites
A covered area with exercise equipment, chairs, and a view through large windows.

12. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥40,465
￥48,629 total
includes taxes & fees
Nov 15 - Nov 16
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

13. 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
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
The price is ￥12,951
￥17,511 total
includes taxes & fees
Nov 18 - Nov 19
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A forested area with a bench and a fire pit.

14. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
The price is ￥35,948
￥58,036 total
includes taxes & fees
Dec 14 - Dec 15
Historic, private riverfront cottage in peaceful Greenwich
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

15. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥16,948
￥44,870 total
includes taxes & fees
Nov 18 - Nov 19
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

16. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is ￥23,966
￥39,863 total
includes taxes & fees
Nov 15 - Nov 16
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

17. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥27,437
￥51,539 total
includes taxes & fees
Nov 15 - Nov 16
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A wooden staircase leading to a gazebo in a forested area with a metal railing.

18. 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
8.6 out of 10, Excellent, (7 reviews)
"Amazing host I appreciate everything she did for me"
United States
CSQUARED A.
The price is ￥35,975
￥45,904 total
includes taxes & fees
Nov 14 - Nov 15
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
An outdoor patio with a fire pit, green chairs, and a table.

19. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ￥20,434
￥46,232 total
includes taxes & fees
Nov 16 - Nov 17
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Living area

20. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥17,460
￥31,927 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 1-bedroom retreat minutes from West Point!
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

Hampton Inn & Suites Teaneck Glenpointe

Hampton Inn & Suites Teaneck Glenpointe

10/10 Excellent
"Pleasant surprise for a last minute booking on a road trip!"
Lorna 1-night trip
Posted 3 hours ago
Hampton Inn & Suites 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:

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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 Theater, 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.