Pleasantville Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Pleasantville vacation rentals

Property grounds

Vacation Home in Greenwich

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥21,158
￥42,793 total
includes taxes & fees
Mar 10 - Mar 11
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

Vacation Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥24,850
￥51,456 total
includes taxes & fees
Mar 11 - Mar 12
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Cottage in Fort Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (132 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥29,663
￥48,014 total
includes taxes & fees
Mar 10 - Mar 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Private kitchen

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,300
￥43,945 total
includes taxes & fees
Mar 10 - Mar 11
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior detail

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥31,570
￥84,142 total
includes taxes & fees
Mar 12 - Mar 13
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Fridge, microwave, oven, stovetop

Vacation Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,501
￥65,869 total
includes taxes & fees
Mar 10 - Mar 11
Contemporary Cozy Cottage
Property grounds

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥25,560
￥62,765 total
includes taxes & fees
Mar 12 - Mar 13
Seabreeze at the beach west beach Stamford ct.
TV

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
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.
The price is ￥14,745
￥29,736 total
includes taxes & fees
Mar 23 - Mar 24
Cozy 1-bedroom retreat minutes from West Point!
Offices

Apartment in Downtown Stamford

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,720
￥48,691 total
includes taxes & fees
Mar 11 - Mar 12
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Terrace/patio

Vacation Home in Southeast Yonkers

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
8.2 out of 10, Very Good, (18 reviews)
"Great location"
United States
Jordan S.
The price is ￥14,910
￥21,275 total
includes taxes & fees
Mar 14 - Mar 15
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥11,834
￥40,678 total
includes taxes & fees
Mar 10 - Mar 11
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
TV

Apartment in Port Chester

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
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
The price is ￥34,712
￥60,817 total
includes taxes & fees
Mar 11 - Mar 12
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Dining

Apartment in Fort Lee

Gorgeous, 2- bedroom apartment walking distance to GWB!
9.8 out of 10, Exceptional, (10 reviews)
"Clean, modern, convenient property. Online pictures were accurate, check in was easy. Highly recommend. Would stay there again without hesitation."
United States
Rebecca
The price is ￥31,240
￥56,411 total
includes taxes & fees
Mar 21 - Mar 22
Gorgeous, 2- bedroom apartment walking distance to GWB!
Property grounds

Apartment in Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck 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.
The price is ￥17,324
￥24,348 total
includes taxes & fees
Mar 10 - Mar 11
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥16,882
￥56,901 total
includes taxes & fees
Mar 22 - Mar 23
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

Villa in White Plains

Luxury NYC Home Game Room Free Parking
4.0 star property
The price is ￥86,779
￥122,763 total
includes taxes & fees
Mar 10 - Mar 11
Luxury NYC Home Game Room Free Parking
TV, fireplace, books, offices

Vacation Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
The price is ￥57,905
￥137,106 total
includes taxes & fees
Mar 10 - Mar 11
New Beach Home near Stamford Downtown/Shippan
TV, fireplace, offices

Vacation Home in Historic District

Family Cottage with 4 King Beds and Fire Pit
10.0 out of 10, Exceptional, (10 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is ￥33,765
￥85,138 total
includes taxes & fees
Apr 1 - Apr 2
Family Cottage with 4 King Beds and Fire Pit
Living area

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is ￥31,398
￥59,420 total
includes taxes & fees
Mar 10 - Mar 11
Luxury 3BR Home Game Room Free Parking
Living area

Vacation Home in Lincoln Park

Cheerful Home in Yonkers NY
7.6 out of 10, Good, (4 reviews)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is ￥39,445
￥92,895 total
includes taxes & fees
Mar 10 - Mar 11
Cheerful Home in Yonkers NY
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

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

8/10 Good
"I can appreciate this place . Has the needed amenities and the property is fairly well kept and the room has adequate temp control and the view is great. They do need a bit more parking . "
Jasmine 1-night trip
Posted 2 hours ago
LIV Hotel Bronx - Newly Built

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 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental outside of Pleasantville is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.