Pleasantville Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Pleasantville vacation rentals

Property grounds

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, (31 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
$254 nightly
The price is $288
Apr 20 - Apr 21
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$164 nightly
The price is $178
Apr 27 - Apr 28
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio

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
Apr 20 - Apr 21
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
$367 nightly
The price is $389
Apr 20 - Apr 21
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$291 nightly
The price is $330
Apr 28 - Apr 29
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$269 nightly
The price is $269
Apr 20 - Apr 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$438 nightly
The price is $483
Apr 20 - Apr 21
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (16 reviews)
"Excellent space and accommodations. "
United States
angela c.
$185 nightly
The price is $206
Apr 27 - Apr 28
Total with taxes and fees
Piermont Oasis
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (19 reviews)
"Great Unit."
United States
Rudy R.
$299 nightly
The price is $307
Apr 20 - Apr 21
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
$276 nightly
The price is $313
Apr 20 - Apr 21
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Luxury Apartment | Living area

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
10.0 out of 10, Exceptional, (1 review)
$255 nightly
The price is $285
Apr 27 - Apr 28
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area
Private kitchen

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
$271 nightly
The price is $310
Apr 20 - Apr 21
Total with taxes and fees
Modern 1BR Apt / Free Parking / Near NYC
Dining

Gorgeous, 2- bedroom apartment walking distance to GWB!

Gorgeous, 2- bedroom apartment walking distance to GWB!
Fort Lee
10.0 out of 10, Exceptional, (11 reviews)
"Yes nice place"
United States
Scott b.
$338 nightly
The price is $373
Apr 20 - Apr 21
Total with taxes and fees
Gorgeous, 2- bedroom apartment walking distance to GWB!
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
$430 nightly
The price is $492
May 1 - May 2
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
Smart TV

Comfortable 1BR Apt / Parking / Perfect for Families & Groups

Comfortable 1BR Apt / Parking / Perfect for Families & Groups
Bryn Mawr
$303 nightly
The price is $356
Apr 20 - Apr 21
Total with taxes and fees
Comfortable 1BR Apt / Parking / Perfect for Families & Groups
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
$310 nightly
The price is $325
Apr 20 - Apr 21
Total with taxes and fees
Luxury House Near West Point
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
$361 nightly
The price is $413
Apr 22 - Apr 23
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Living area

Modern 1BR / Free Parking / Comfortable Stay

Modern 1BR / Free Parking / Comfortable Stay
Bryn Mawr
$264 nightly
The price is $311
Apr 30 - May 1
Total with taxes and fees
Modern 1BR / Free Parking / Comfortable Stay
Property grounds

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
7.6 out of 10, Good, (4 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.
$178 nightly
The price is $202
Apr 21 - Apr 22
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (15 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$423 nightly
The price is $429
Apr 20 - Apr 21
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + 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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

8/10 Good
"Bed ok a little soft for my taste... not enough towels and better lighting would have been good"
Mendy 2-night trip
Posted 1 hour ago
Baymont by Wyndham White Plains - Elmsford

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 $135 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 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental outside of Pleasantville is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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.