Pleasantville Holiday Rentals : Search Short-Term Rentals

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

Modern Luxury Home w GameRoom & Parking : This holiday 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 that you can cook with friends or family.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pleasantville holiday 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 traveller

includes taxes & fees

3 Nov - 4 Nov

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

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

Ossining

Karen O.

includes taxes & fees

4 Nov - 5 Nov

A stone staircase leading to a house with a stone wall and a metal gate.

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

Croton-on-Hudson

Eva C.

includes taxes & fees

5 Nov - 6 Nov

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.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

3 Nov - 4 Nov

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

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

CROTON HDSN

Margaret S.

includes taxes & fees

3 Nov - 4 Nov

6. 1 King Bed | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

3 Nov - 4 Nov

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

7. 2 Full Beds | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

3 Nov - 4 Nov

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

8. 1 Queen Bed | Non-Smoking

Elmsford

includes taxes & fees

3 Nov - 4 Nov

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

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

Croton-on-Hudson

Mateo A.

includes taxes & fees

3 Nov - 4 Nov

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

10. Piermont Oasis

Piermont

Megan D.

includes taxes & fees

10 Nov - 11 Nov

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

includes taxes & fees

15 Nov - 16 Nov

A room with large windows overlooking a lake and greenery.

12. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

includes taxes & fees

3 Nov - 4 Nov

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

13. 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.

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with stainless steel appliances, light wood cabinets, and a red toaster.

14. Flex Comfort Apts of Westchester #2

Rye Brook

Andres T.

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

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

Southeast Yonkers

Jordan S.

includes taxes & fees

3 Nov - 4 Nov

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

16. Stamford Suites

Downtown Stamford

Christine

includes taxes & fees

8 Nov - 9 Nov

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

Downtown Stamford

Marisa C.

includes taxes & fees

10 Nov - 11 Nov

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

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

Highland Falls

Andrew L.

includes taxes & fees

3 Nov - 4 Nov

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Pleasantville Hotel Reviews

Royal Regency Hotel

10/10 Excellent

"Great to stay recommended"

DoubleTree by Hilton Fort Lee - George Washington Bridge

10/10 Excellent

"The hotel was decent overall, but there were a few noticeable issues with parking and room cleanliness. While the cleanliness concerns were not major, we did notice that the window gaps had not been cleaned thoroughly, as there were dead bugs and dust present. Additionally, the bathroom panel was loose or undone, and we were unsure whether it had been left that way by housekeeping or if there was an underlying maintenance issue. The biggest concern, however, was the air conditioning system. We had to request assistance to have it reset because the room was uncomfortably hot. Despite setting the temperature to 70°F, the room remained around 80°F. Over time, the heat became increasingly uncomfortable, and we felt that the staff did not fully understand our frustration with being unable to adjust the room temperature. Although the staff assured us that the system was functioning normally, the room's temperature made it difficult to feel comfortable during our stay."

Find out more about Pleasantville

Everything you need to know about Pleasantville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Pleasantville holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasantville holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasantville holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville holiday 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 holiday.

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 holiday rental in Pleasantville?

Yes, there are holiday rentals in Pleasantville close to Jacob Burns Film Center Theater, or you can select a more secluded option if you're looking for a relaxing stay. Pleasantville is known for its restaurants and sporting events.

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

Modern Luxury Home w GameRoom & Parking: This holiday 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 that 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 wider area, you’ll find Jacob Burns Film Center Media Arts Lab and New York Medical College.

What’s a holiday rental in Pleasantville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pleasantville. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pleasantville holiday rentals

1. 1 Queen Bed | Smoking

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

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

4. Summer Pool Oasis Custom Bar Arcade Pool Table

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

6. 1 King Bed | Non-Smoking

7. 2 Full Beds | Non-Smoking

8. 1 Queen Bed | Non-Smoking

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

10. Piermont Oasis

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

12. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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

14. Flex Comfort Apts of Westchester #2

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

16. Stamford Suites

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

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

Find holiday rentals that suit your style

Top Pleasantville Hotel Reviews

Royal Regency Hotel

Tarrytown House Estate

DoubleTree by Hilton Fort Lee - George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

West Gate Inn Nyack

J House Greenwich

Hampton Inn White Plains/Tarrytown

LIV Hotel Bronx - Newly Built

Hampton Inn & Suites Teaneck Glenpointe

Find out more about Pleasantville

Frequently asked questions

Go further with the Expedia app