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

Pleasantville Vacation 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.

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Dates

November 2026

December 2026

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Our top choices for Pleasantville vacation rentals

A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

1. 1 Queen Bed | Smoking

Elmsford

Anonymous traveler

$121 nightly

Nov 12 - Nov 13

Total with taxes and fees

A compact bathroom with a toilet, sink, and shower.

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

Croton-on-Hudson

Eva C.

$353 nightly

Nov 12 - Nov 13

Total with taxes and fees

3. 1 King Bed | Non-Smoking

Elmsford

Anonymous traveler

$124 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

4. 2 Full Beds | Non-Smoking

Elmsford

Anonymous traveler

$126 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hotel room with a bed, a desk, and a chair.

5. 1 Queen Bed | Non-Smoking

Elmsford

$121 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden staircase leading to a small shed with a slanted roof, surrounded by dense greenery and a stone wall.

6. Piermont Oasis

Piermont

Megan D.

$180 nightly

Nov 18 - Nov 19

Total with taxes and fees

A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

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

Ossining

Karen O.

$747 nightly

Nov 16 - Nov 17

Total with taxes and fees

A nighttime view of a residential street with houses, trees, and parked cars.

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

CROTON HDSN

Margaret S.

$311 nightly

Nov 18 - Nov 19

Total with taxes and fees

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

$916 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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

Croton-on-Hudson

Mateo A.

$355 nightly

Nov 19 - Nov 20

Total with taxes and fees

An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

11. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

$273 nightly

Nov 15 - Nov 16

Total with taxes and fees

A living room with a sofa, a coffee table, a lamp, a staircase, and a bookshelf.

12. Historic, private riverfront cottage in peaceful Greenwich

Greenwich

$320 nightly

Nov 18 - Nov 19

Total with taxes and fees

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

13. Stamford Suites

Downtown Stamford

Christine

$149 nightly

Nov 22 - Nov 23

Total with taxes and fees

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

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

Southeast Yonkers

Jordan S.

$107 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with large windows overlooking a lake and greenery.

15. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

$286 nightly

Nov 12 - Nov 13

Total with taxes and fees

A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

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

Highland Falls

Andrew L.

$288 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Downtown Stamford

Marisa C.

$218 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

New Rochelle

Drew C.

$253 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden staircase leading to a gazebo in a forested area with a metal railing.

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

Greenwich

"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...

Kathleen W.

$252 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a bar stool.

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

Downtown Stamford

michelle b.

$263 nightly

Nov 20 - Nov 21

Total with taxes and fees

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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 hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

SpringHill Suites by Marriott Tarrytown Westchester County

Tarrytown

10/10 Excellent

James

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 spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

Sheraton Tarrytown Hotel

Tarrytown

10/10 Excellent

Jason

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

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 modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

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

An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area.

Sonesta White Plains Downtown

White Plains

10/10 Excellent

Amy

A modern lounge with leather sofas, a patterned rug, and red pendant lights.

Hotel Nyack, a JdV by Hyatt Hotel

Nyack

10/10 Excellent

JASON

A Holiday Inn Express & Suites sign with a bench and flower beds in front.

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

Peekskill

10/10 Excellent

David Allen

A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

Ardsley Acres Hotel Westchester

Ardsley

10/10 Excellent

Valerie

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 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

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 $125 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.

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

Bundle & Save

OneKeyCash

Upfront pricing

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. 1 King Bed | Non-Smoking

4. 2 Full Beds | Non-Smoking

5. 1 Queen Bed | Non-Smoking

6. Piermont Oasis

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

12. Historic, private riverfront cottage in peaceful Greenwich

13. Stamford Suites

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

15. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

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

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

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

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

Find vacation rentals that suit your style

Top Pleasantville Hotel Reviews

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

10/10 Excellent

Find out more about Pleasantville

Everything you need to know about Pleasantville vacation rentals

Pleasantville vacation rentals: An excellent choice for every season

How to find incredible deals on Pleasantville rentals

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?

Explore a world of travel with Expedia