Pleasantville Vacation Rentals

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Dec 12 - Dec 14
In two months
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Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Pleasantville

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Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (76)
"It was great"
United States
Natalie
$120 nightly
The price is $138
Dec 7 - Dec 8
Total with taxes and fees
Stamford Suites
Terrace/patio
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1)
"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."
United States
Anonymous traveler
$687 nightly
The price is $769
Nov 28 - Nov 29
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very Good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$262 nightly
The price is $302
Dec 16 - Dec 17
Total with taxes and fees
Guesthouse at Norwalk Inn
Lounge
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$220 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Reception
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 star property
White Plains
6.8 out of 10, (33)
"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."
United States
Ramon
Global Luxury Suites White Plains
2 bedrooms, in-room safe, WiFi
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Bronx
9.0 out of 10, Wonderful, (8)
"We had a wonderful time. The apartment was exactly as described in the posting. Every room was super clean, bright, and welcoming. We were very comfortable. Eche was very helpful. We appreciated how quickly he responded to our questions. He checked in with us and made sure we had everything we needed. Many nice extra touches made us feel at home. We plan to stay here next time we are in town!"
United States
Karen C.
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
House | Living area
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.0 star property
Southeast Yonkers
7.2 out of 10, Good, (5)
"This was an excellent House My birthday weekend was amazing I totally would book again"
United States
Keisheena
Modern Luxury Home w GameRoom & Parking
Smart TV
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

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

Bronx
9.8 out of 10, Exceptional, (13)
"Excellent property close to Fordham, very clean and nice amenities! Hope to stay here on our next visit to see our daughter at Fordham."
United States
Amy B.
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
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, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
$272 nightly
The price is $308
Nov 29 - Nov 30
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Smart TV
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

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

Scarsdale
9.0 out of 10, Wonderful, (4)
"Space was clean, nice, and hosts were very helpful and communicative."
United States
Steven C.
$282 nightly
The price is $323
Nov 30 - Dec 1
Total with taxes and fees
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
Living area
Luxury NY Home close to NYC

Luxury NY Home close to NYC

2.0 star property
Southeast Yonkers
Luxury NY Home close to NYC
Fridge, microwave, oven, stovetop
Marvelous 5-bedroom house with AC in Yonkers

Marvelous 5-bedroom house with AC in Yonkers

2.0 star property
Bryn Mawr
2.0 out of 10, (1)
"Cancelled my stay at check out time while I was at the NY airport— said there was a “power outage”. “Upgraded” me to a luxury property that turned out to be a dirty 3rd floor walk up. When I asked for a refund, they lied to VRBO and said I never showed up. I had to prove to VRBO with texts and phone records that they cancelled me. I suspected a bait and switch. Also, VRBO had to start an investigation because the phone number from the owner was an unknown number—my information had been...
United States
Amy L.
Marvelous 5-bedroom house with AC in Yonkers
1 bedroom, iron/ironing board, free WiFi, bed sheets
Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

White Plains
10.0 out of 10, Exceptional, (1)
"This location was tranquil and close to everything I expected for meals and entertainment. Easy to get to and felt warm and inviting. Fayeem was responsive and helpful towards my requests. I look forward to staying here again. Thank you!"
United States
Moses A.
Elegant Hideaway • Free Parking
In-room dining
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4.0 star property
Southeast Yonkers
2.0 out of 10, (1)
"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."
United States
Ebony
Luxury Living in the Heart of NY
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

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

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
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
8.2 out of 10, Very Good, (18)
"Great place great location"
United States
Daquan H.
$115 nightly
The price is $135
Nov 29 - Nov 30
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Property grounds
Comfortable 1 family home in Tuckahoe that's near train

Comfortable 1 family home in Tuckahoe that's near train

Tuckahoe
$632 nightly
The price is $704
Nov 28 - Nov 29
Total with taxes and fees
Comfortable 1 family home in Tuckahoe that's near train
Luxury House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4.0 star property
White Plains
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
Luxury NY Home with Free Parking
Fridge, microwave, oven, stovetop
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Northeast Yonkers
8.8 out of 10, Excellent, (44)
"Perfect place and plenty of parking. "
United States
Alyssa M.
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
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

Sleepy Hollow Hotel

Sleepy Hollow Hotel

10/10 Excellent
"excellent place "
Boruch 1-night trip
Posted 1 day ago
Sleepy Hollow 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 $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 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 of 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.