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

Pleasantville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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
$120 nightly
The price is $137
Nov 24 - Nov 25
Total with taxes and fees
1 Queen Bed | Smoking
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

2. 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.
$821 nightly
The price is $843
Nov 3 - Nov 4
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A stone staircase leading to a house with a stone wall and a metal gate.

3. 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, (27 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$372 nightly
The price is $425
Nov 5 - Nov 6
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
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.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$947 nightly
The price is $1,054
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

5. 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.
$315 nightly
The price is $360
Nov 3 - Nov 4
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

6. 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
$123 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
1 King Bed | Non-Smoking
A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

7. 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
$126 nightly
The price is $144
Nov 1 - Nov 2
Total with taxes and fees
2 Full Beds | Non-Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

8. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
8.0 out of 10, Very good, (6 reviews)
$120 nightly
The price is $138
Nov 1 - Nov 2
Total with taxes and fees
1 Queen Bed | Non-Smoking
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

9. '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.
$361 nightly
The price is $413
Nov 3 - Nov 4
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A garden with a stone wall, a wooden fence, and a gravel path.

10. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Megan D.
$189 nightly
The price is $211
Nov 10 - Nov 11
Total with taxes and fees
Piermont Oasis
A covered area with exercise equipment, chairs, and a view through large windows.

11. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
$261 nightly
The price is $290
Nov 15 - Nov 16
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A modern kitchen with a built-in oven, a large window, and a flat-screen TV mounted above the sink.

12. Luxury Urban Retreat + Spacious & Stylish

Luxury Urban Retreat + Spacious & Stylish
White Plains
$580 nightly
The price is $663
Oct 31 - Nov 1
Total with taxes and fees
Luxury Urban Retreat + Spacious & Stylish
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

13. 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.
$305 nightly
The price is $346
Nov 1 - Nov 2
Total with taxes and fees
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.

14. 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)
"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.
$264 nightly
The price is $299
Oct 30 - Oct 31
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A living room with a brown leather sofa, a green sofa, a coffee table, and a red rug. There are framed pictures on the wall and a radio on a wooden cabinet.

15. Flex Comfort Apts of Westchester #2

Flex Comfort Apts of Westchester #2
Rye Brook
9.4 out of 10, Exceptional, (32 reviews)
"Good Stay!"
United States
Andres T.
$304 nightly
The price is $309
Nov 1 - Nov 2
Total with taxes and fees
Flex Comfort Apts of Westchester #2
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

16. 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.
$115 nightly
The price is $135
Nov 2 - Nov 3
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

17. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (201 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$169 nightly
The price is $194
Nov 1 - Nov 2
Total with taxes and fees
Stamford Suites
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

18. 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
$680 nightly
The price is $778
Oct 30 - Oct 31
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
Living area

19. 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.
$239 nightly
The price is $271
Nov 2 - Nov 3
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

20. 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.
$278 nightly
The price is $285
Nov 2 - Nov 3
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to 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.
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

West Gate Inn Nyack

West Gate Inn Nyack

10/10 Excellent
"Awesome place will still again if in area"
Joshua 1-night trip
Posted 4 hours ago
West Gate Inn Nyack

Find out more about Pleasantville

Everything you need to know about Pleasantville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasantville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasantville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasantville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasantville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $194 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasantville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasantville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasantville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.