Pleasantville Vacation Rentals from AED 290: Search Short-Term Rentals

Q: 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.

A calm lake surrounded by autumn-colored trees reflecting in the water.

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Our top choices for Pleasantville vacation rentals

A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

1. 1 Queen Bed | Smoking

Elmsford

Anonymous traveler

AED 501 total

includes taxes & fees

29 Nov - 30 Nov

A wooden deck with a railing overlooking a body of water and trees.

2. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson

Eva C.

AED 1,483 total

includes taxes & fees

23 Nov - 24 Nov

A garden pathway with stepping stones, surrounded by dense foliage and a stone wall.

3. Piermont Oasis

Piermont

Megan D.

AED 736 total

includes taxes & fees

29 Nov - 30 Nov

A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

4. 2 Full Beds | Non-Smoking

Elmsford

Anonymous traveler

AED 525 total

includes taxes & fees

23 Nov - 24 Nov

5. 1 King Bed | Non-Smoking

Elmsford

Anonymous traveler

AED 513 total

includes taxes & fees

29 Nov - 30 Nov

6. 1 Queen Bed | Non-Smoking

Elmsford

AED 501 total

includes taxes & fees

29 Nov - 30 Nov

A rectangular swimming pool with a brick wall and a basketball hoop.

7. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining

Karen O.

AED 2,801 total

includes taxes & fees

16 Nov - 17 Nov

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

8. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

CROTON HDSN

Margaret S.

AED 1,252 total

includes taxes & fees

18 Nov - 19 Nov

A large, two-story house with a prominent front entrance, multiple windows, and a driveway.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

AED 3,873 total

includes taxes & fees

18 Nov - 19 Nov

A modern kitchen with white cabinetry, a stainless steel stove, a dishwasher, and a tiled backsplash.

10. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Croton-on-Hudson

Mateo A.

AED 1,490 total

includes taxes & fees

19 Nov - 20 Nov

A modern hotel room with a large window, a sofa, a coffee table, and a decorative statue.

11. Stamford Suites

Downtown Stamford

Christine

AED 629 total

includes taxes & fees

22 Nov - 23 Nov

A covered area with exercise equipment, chairs, and a view through large windows.

12. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

AED 1,117 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a patterned bedspread, a headboard, bedside tables, and a window with curtains.

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

Southeast Yonkers

Jordan S.

AED 395 total

includes taxes & fees

16 Nov - 17 Nov

A cozy room with a large window, a comfortable seating area with cushions, a wooden deck outside, and a decorative quilt on the bed.

14. Historic, private riverfront cottage in peaceful Greenwich

Greenwich

AED 1,331 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Highland Falls

Andrew L.

AED 1,027 total

includes taxes & fees

17 Nov - 18 Nov

16. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Downtown Stamford

Marisa C.

AED 946 total

includes taxes & fees

22 Nov - 23 Nov

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

17. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

AED 1,200 total

includes taxes & fees

15 Nov - 16 Nov

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

Greenwich

CSQUARED A.

AED 1,055 total

includes taxes & fees

14 Nov - 15 Nov

An outdoor patio with a fire pit, green chairs, and a table.

19. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle

Drew C.

AED 1,062 total

includes taxes & fees

16 Nov - 17 Nov

20. Cozy 1-bedroom retreat minutes from West Point!

Highland Falls

Zack C.

AED 733 total

includes taxes & fees

8 Dec - 9 Dec

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Find vacation rentals that suit your style

Top Pleasantville Hotel Reviews

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

10/10 Excellent

Lorena

A bar area with a long counter, multiple chairs, and a television mounted on the wall.

SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

10/10 Excellent

James

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

Baymont by Wyndham White Plains - Elmsford

Elmsford

10/10 Excellent

Norma Jean

An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

Westchester Marriott

Tarrytown

10/10 Excellent

This hotel was nice, the only thing I was not a big fan of was the overcrowded lobby. I felt like it was a hassle to enter and exit the doors because people were permitted to block doorways and the main hallway to get to the elevators. I understand people are eager to congregate, but a kind reminder to move over for guests just trying to get up to their rooms by staff would have made the experience much more welcoming.

KELLY

A modern hotel lobby with a central sofa, two armchairs, a coffee table, and a chandelier. The room features a large window with a city view.

Cambria Hotel & Suites - White Plains Downtown

White Plains

10/10 Excellent

Keeping in mind its 3-star classification, this hotel does not disappoint. Front desk staff is outstanding. Metro-North station is in easy walking distance. Of special note: In partnership with the Chazz Palminteri restaurant next door, guests can order a meal, get it delivered and charged to the room. Very nice option when traveling all day. On a lesser note, the slamming doors made a lot of disruption. Soft close, as in other hotels, would improve the guest experience and be worth the...

William

A Sheraton hotel with a large entrance, multiple windows, and a Starbucks on the ground floor.

Sheraton Tarrytown Hotel

Tarrytown

10/10 Excellent

Jason

A modern high-rise hotel with a curved facade, multiple floors, and a well-lit entrance.

Residence Inn by Marriott White Plains Westchester County

White Plains

10/10 Excellent

The receptionist was awesome, professional, and really connects with us, very positive, courteous, informative, and shows a lot of customer care, great service. The corner suite was pretty awesome spacious, and felt like I was in a new home or an apartment. Very clean. I would recommend the suites , especially with the kitchen for multiple nights and long stays. I've been to the Chinese restaurant, and it's got awesome dim sum, and pretty authentic. Everything else you want is local and a few...

Anonymous traveler

An outdoor seating area with modern furniture, a fire pit, and ambient lighting.

Sonesta White Plains Downtown

White Plains

10/10 Excellent

Amy

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

Hotel MTK Mount Kisco

Mount Kisco

10/10 Excellent

Overall our stay at MTK was very positive. Generally staff was responsive and friendly but not our experience in the restaurant. Service person barely greeted us, sat looking at his phone, apparently not checking on our food for which we waited a very long time. He made it quite clear that he did not enjoy his job and did not want to be there. However, we definitely would stay at MTK again without hesitation.

Shirley

A buffet with labeled trays of turkey sausage and cookies.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

David Allen

Hotel Nyack, a JdV by Hyatt Hotel

Nyack

10/10 Excellent

JASON

A multi-story hotel with a prominent "Hyatt Place" sign, featuring a modern architectural design with a mix of glass and brick facades.

Hyatt Place New York/Yonkers

Southeast Yonkers

10/10 Excellent

Sarah

A spacious hotel dining area with a long table, multiple chairs, and modern pendant lighting.

Hampton Inn & Suites Yonkers - Westchester

Northeast Yonkers

10/10 Excellent

Everything about this hotel was great: check-in was easy, the room was clean and spacious, and most importantly, the staff was really friendly and helpful. An example: I asked one of the women who was keeping things clean in the breakfast are what the flavor of the two muffins were. (Did I mention that there was a full breakfast?) A few minutes after answering, she came back to tell me that they also had blueberry in the back, if I was interested. Above and beyond!

Susan

A neatly made bed with white linens and a beige throw blanket, a bedside table with a lamp, and a framed cityscape picture on the wall.

Ardsley Acres Hotel Westchester

Ardsley

10/10 Excellent

Valerie

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.

Pleasantville Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pleasantville vacation rentals

1. 1 Queen Bed | Smoking

2. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

3. Piermont Oasis

4. 2 Full Beds | Non-Smoking

5. 1 King Bed | Non-Smoking

6. 1 Queen Bed | Non-Smoking

7. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

9. Summer Pool Oasis Custom Bar Arcade Pool Table

10. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

11. Stamford Suites

12. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

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

14. Historic, private riverfront cottage in peaceful Greenwich

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

16. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

17. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

18. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

19. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

20. Cozy 1-bedroom retreat minutes from West Point!

Find vacation rentals that suit your style

Top Pleasantville Hotel Reviews

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Pleasantville?

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

What’s there to see and do in Pleasantville?

What’s a vacation rental in Pleasantville like?