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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pleasantville vacation rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
$732 nightly
The price is $815
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
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.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,008 nightly
The price is $1,123
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

3. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
$709 nightly
The price is $790
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

4. 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.
$951 nightly
The price is $977
Nov 9 - Nov 10
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.

5. 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 16 - Oct 17
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A stone staircase leading to a house with a stone wall and a metal gate.

6. 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, (25 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
Oct 18 - Oct 19
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern kitchen with a built-in oven, a large window, and a flat-screen TV mounted above the sink.

7. Luxury Urban Retreat + Spacious & Stylish

Luxury Urban Retreat + Spacious & Stylish
White Plains
$584 nightly
The price is $668
Oct 17 - Oct 18
Total with taxes and fees
Luxury Urban Retreat + Spacious & Stylish
A hotel room with a bed, a desk, and a chair.

8. 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
$124 nightly
The price is $141
Oct 18 - Oct 19
Total with taxes and fees
1 King Bed | Non-Smoking
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

9. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (193 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$164 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
Stamford Suites
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

10. 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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
$611 nightly
The price is $680
Oct 16 - Oct 17
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

11. '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.
$376 nightly
The price is $430
Oct 26 - Oct 27
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

12. 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)
"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.
$314 nightly
The price is $359
Nov 3 - Nov 4
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

13. '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.
$270 nightly
The price is $309
Nov 1 - Nov 2
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A covered area with exercise equipment, chairs, and a view through large windows.

14. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
$255 nightly
The price is $284
Nov 8 - Nov 9
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

15. 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
$330 nightly
The price is $380
Oct 18 - Oct 19
Total with taxes and fees
Guesthouse at Norwalk Inn
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

16. 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
$121 nightly
The price is $138
Oct 18 - Oct 19
Total with taxes and fees
1 Queen Bed | Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

17. 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 $145
Oct 18 - Oct 19
Total with taxes and fees
2 Full Beds | Non-Smoking
A motel with a blue awning and a '6 Now Open' sign.

18. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
9.0 out of 10, Wonderful, (4 reviews)
"Short trip so just needed something quick, location near Westchester Airport suited us well."
United States
Anonymous traveler
$121 nightly
The price is $138
Oct 18 - Oct 19
Total with taxes and fees
1 Queen Bed | Non-Smoking
A breakfast buffet with pastries, fruits, and a coffee station.

19. 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
$1,134 nightly
The price is $1,263
Oct 16 - Oct 17
Total with taxes and fees
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

20. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$1,084 nightly
The price is $1,207
Oct 16 - Oct 17
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
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

Radio Hotel

Radio Hotel

10/10 Excellent
"Very clean and secured."
Carolina Cedano 3-night trip
Posted 19 hours ago
Radio Hotel

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 $189 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.