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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$748 nightly
The price is $833
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

2. 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.
$756 nightly
The price is $842
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

3. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
$133 nightly
The price is $152
Oct 4 - Oct 5
Total with taxes and fees
1 Queen Bed | Smoking
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

4. 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.
$295 nightly
The price is $337
Oct 4 - Oct 5
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A stone staircase leading to a house with a stone wall and a metal gate.

5. 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.
$372 nightly
The price is $425
Oct 3 - Oct 4
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
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.

6. '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.
$256 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A motel with a blue awning and a '6 Now Open' sign.

7. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
$133 nightly
The price is $152
Oct 5 - Oct 6
Total with taxes and fees
1 Queen Bed | Non-Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

8. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
$139 nightly
The price is $159
Oct 4 - Oct 5
Total with taxes and fees
2 Full Beds | Non-Smoking
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

9. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
$136 nightly
The price is $156
Oct 5 - Oct 6
Total with taxes and fees
1 King Bed | Non-Smoking
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.
$372 nightly
The price is $425
Oct 11 - Oct 12
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

11. 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.
$969 nightly
The price is $997
Oct 5 - Oct 6
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.

12. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,107 nightly
The price is $1,233
Oct 5 - Oct 6
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A garden with a stone wall, a wooden fence, and a gravel path.

13. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (22 reviews)
"Great place to stay! "
United States
Megan D.
$188 nightly
The price is $209
Oct 27 - Oct 28
Total with taxes and fees
Piermont Oasis
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
$281 nightly
The price is $313
Nov 1 - Nov 2
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

15. 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
Oct 4 - Oct 5
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.

16. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$146 nightly
The price is $168
Oct 12 - Oct 13
Total with taxes and fees
Stamford Suites
A campfire with a wooden table and benches by a 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, (42 reviews)
"Nice stay"
United States
Christopher J.
$275 nightly
The price is $311
Oct 7 - Oct 8
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.

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
8.0 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.
$266 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A stone staircase leading up to a house, surrounded by greenery and a blue tarp.

19. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
$336 nightly
The price is $384
Oct 11 - Oct 12
Total with taxes and fees
Garden Loft with Patios & Green Space · Westchester Retreat
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
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$299 nightly
The price is $307
Oct 4 - Oct 5
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.
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Top Pleasantville Hotel Reviews

Hampton Inn & Suites Teaneck Glenpointe

Hampton Inn & Suites Teaneck Glenpointe

8/10 Good
"Pool was cloudy and didn’t appear to be working well. The gym looked nice. I noticed the light automatically shuts off as when I walked in to check it out someone was working out in the dark. We had a nice city view. Bar wasn’t open until ten I requested a soda that they advertised at the front desk and you would have thought I was asking for a golden ring or something. The staff looked at me in complete disgust. I asked for one for myself and my husband and was told I could have only one per room and I’d have to buy the second one. I again questioned there are two of us, after she rolled her eyes at me I could see I was obviously going to have to pay for a second drink. So staff was slightly rude. It was pricey for what it was No pool/hot tub Breakfast was nothing like some of the other reviews I read. Some cereal yogurt waffles you know the regular stuff Close to manhattan about 30 minute drive Overall if I can get a deal on this app then I’d stay again but I’m not going out of my way to seek this hotel out."
Seth 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Teaneck Glenpointe

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 $168 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.