Pleasantville Vacation Rentals from CA $130: Short-Term Rentals for 2025

Q: What are some of the best vacation rentals that Pleasantville has to offer?

3BR Prime Luxury near NYC w Arcade Room : This vacation home rental outside Pleasantville is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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Vacation Rentals in Pleasantville

Our top choices for Pleasantville vacation rentals

"Excellent sleep"

CA $210 total

includes taxes & fees

Sep 14 - Sep 15

"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."

CA $1,065 total

includes taxes & fees

Sep 11 - Sep 12

"This property is a wonderful alternative to the expensive hotels around Greenwich. It was no frills - there are two bedrooms with large beds and TVs, a bathroom, and kitchenette with a pod coffeemaker. We didn't spend a lot of time there, which worked for us. It's quiet, backcountry Greenwich, on a pond. We saw a fox and a baby deer and fell asleep to the bullfrogs. "

CA $404 total

includes taxes & fees

Sep 15 - Sep 16

"Everything was very clean and cozy.We have enjoyed our stay there. "

"This was not what was shown for it to be. The couch was not as pictured it was a love set with terrible comfort only fit two people. The freezer in small fridge picture showed a full fridge the fire alarm did not have a battery in it no fire extinguisher in area. No towels for kitchen or hot pads or wash clothes for bathroom. Chairs and bench in dining room were terribly uncomfortable to sit on just plastic. Bars on windows doors for bedrooms had locks on inside. We had to spend 265.00...

CA $582 total

includes taxes & fees

Sep 14 - Sep 15

Standard Room, 1 King Bed, Main Building | Property entrance

"it was amazing will stay again food was good comfort was great "

CA $392 total

includes taxes & fees

Sep 14 - Sep 15

"Saud was fantastic and very accommodating and communicative loved his home, and would definitely would book him again!"

CA $443 total

includes taxes & fees

Sep 15 - Sep 16

"The property was perfect for our weekend! Truly truly a beautiful view! "

CA $425 total

includes taxes & fees

Sep 11 - Sep 12

"This was an excellent House My birthday weekend was amazing I totally would book again"

"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."

"Very clean, comfortable, and quiet property. Although advertised one car parking, actually can park 2, which is good since limited street parking in a crowded neighborhood. Highly recommended if you're staying in the NYC area."

"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "

CA $445 total

includes taxes & fees

Sep 12 - Sep 13

32-inch flat-screen TV with cable channels, TV

"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"

"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."

"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."

"Great place great location"

CA $186 total

includes taxes & fees

Sep 11 - Sep 12

1 bedroom, iron/ironing board, free WiFi, bed sheets

"If I could give this place zero stars, I would. Upon arrival, I received no check-in information, which immediately set the tone for a frustrating experience. When I got to the property, the front door was already open, raising serious concerns about security. Inside, the floors were dirty, the beds were unmade, and the trash from the previous guests had not been removed. There were bugs throughout the space, and the front door handle was broken, making the property feel unsafe and poorly...

"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"

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Top Pleasantville Hotel Reviews

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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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasantville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasantville vacation rentals we have selected for you start as low as CA $130 per night. Entering your travel dates in the search wizard 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.

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Frequently asked questions

Can I find a vacation rental in Pleasantville?

Yes, we give you a choice of vacation rentals close to popular attractions in Pleasantville, 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?

3BR Prime Luxury near NYC w Arcade Room: This vacation home rental outside Pleasantville is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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 Union Church of Pocantico Hills.

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.

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Pleasantville Vacation Rentals

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Vacation Rentals in Pleasantville

Our top choices for Pleasantville vacation rentals

Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Stunning 2BR next to Bronx Zoo

Guesthouse at Norwalk Inn

4-bedroom vacation home just 20 mins to NYS times Square.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Modern Luxury Home w GameRoom & Parking

Global Luxury Suites White Plains

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Brand New Private Share Room

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Luxury Living in the Heart of NY

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Elegant Hideaway • Free Parking

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

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