Holiday Rentals Pleasantville from £105: Find Short-Term Rentals & Holiday Accommodations

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.

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In two weeks

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Our top choices for Pleasantville holiday rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Ossining

includes taxes & fees

21 Oct - 22 Oct

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.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

3. Snow Days & City Escapes: Spacious Ossining Home

Ossining

Justeen P.

includes taxes & fees

21 Oct - 22 Oct

An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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

Ossining

natalie l.

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

5. Luxury NYC Home Game Room Free Parking

White Plains

"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...

Jorge

includes taxes & fees

24 Oct - 25 Oct

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

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

Croton-on-Hudson

Eva C.

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with a built-in oven, a large window, and a flat-screen TV mounted above the sink.

7. Luxury Urban Retreat + Spacious & Stylish

White Plains

includes taxes & fees

17 Oct - 18 Oct

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

8. 1 King Bed | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

20 Oct - 21 Oct

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

9. Stamford Suites

Downtown Stamford

Alice

includes taxes & fees

18 Oct - 19 Oct

A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

10. Luxury NYC Home with Free Parking for 12

White Plains

daniel

includes taxes & fees

16 Oct - 17 Oct

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

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

Croton-on-Hudson

Mateo A.

includes taxes & fees

27 Oct - 28 Oct

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

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

CROTON HDSN

Margaret S.

includes taxes & fees

3 Nov - 4 Nov

A white door with a brass lock and a small mailbox to the left.

13. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Croton-on-Hudson

Ann S.

includes taxes & fees

1 Nov - 2 Nov

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

14. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

includes taxes & fees

8 Nov - 9 Nov

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

15. Guesthouse at Norwalk Inn

Historic District

Ronbert

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

16. 1 Queen Bed | Smoking

Elmsford

Anonymous traveller

includes taxes & fees

20 Oct - 21 Oct

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

17. 2 Full Beds | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

20 Oct - 21 Oct

A motel with a blue awning and a '6 Now Open' sign.

18. 1 Queen Bed | Non-Smoking

Elmsford

Anonymous traveller

includes taxes & fees

20 Oct - 21 Oct

A breakfast buffet with pastries, fruits, and a coffee station.

19. 3BR Prime Luxury NY - Free Parking

White Plains

Osmond

includes taxes & fees

27 Oct - 28 Oct

A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

20. Prime Luxe 3-BR NYC - Free Parking

White Plains

includes taxes & fees

17 Oct - 18 Oct

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Top Pleasantville Hotel Reviews

Hyatt Regency Greenwich

8/10 Good

"The property is very pretty. Unfortunately the greenhouse style ceiling in the lobby was leaking due to heavy rain. The rooms were clean but the bathroom needs some work. Not quite clean enough for my standards. It needs some freshening up. The staff is friendly. Breakfast was ok but the staff seems to need more training to meet the standards of this type of hotel."

Baymont by Wyndham White Plains - Elmsford

8/10 Good

"It was very clean. Bed was comfortable. Elevators had issues. The pool water was not as warm as others described. Overall the stay was good. I would stay there again."

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, apart-hotels, 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 favorite 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 depends 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 £105 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 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.

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Check prices for these dates

Our top choices for Pleasantville holiday rentals

1. Snow Days & City Escapes: Spacious Ossining Home

2. Summer Pool Oasis Custom Bar Arcade Pool Table

3. Snow Days & City Escapes: Spacious Ossining Home

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

5. Luxury NYC Home Game Room Free Parking

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