Pleasantville Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Pleasantville holiday rentals

Fridge, microwave, oven, stovetop

Stylish 2BR Midtown West Near Times Square

Stylish 2BR Midtown West Near Times Square
Bronx
10.0 out of 10, Exceptional, (1 review)
"This is a great location everything you need right at your doorstep. Good food, public transportation. We had a great time. Thank you!"
United States
Bianca N.
The price is HK$695
HK$2,810 total
includes taxes & fees
8 Feb - 9 Feb
Stylish 2BR Midtown West Near Times Square
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$701
HK$1,449 total
includes taxes & fees
9 Feb - 10 Feb
Cozy 1-bedroom retreat minutes from West Point!
Private kitchen

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
The price is HK$774
HK$2,030 total
includes taxes & fees
9 Feb - 10 Feb
Luxury 1BR located in Prime Yonkers Area
Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$930
HK$2,228 total
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking
Property grounds

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is HK$883
HK$1,930 total
includes taxes & fees
9 Feb - 10 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$813
HK$2,250 total
includes taxes & fees
18 Feb - 19 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$641
HK$2,632 total
includes taxes & fees
9 Feb - 10 Feb
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is HK$859
HK$2,126 total
includes taxes & fees
8 Feb - 9 Feb
Luxe 1BR Oasis - Prime NY Stay
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,055
HK$2,168 total
includes taxes & fees
8 Feb - 9 Feb
Charming 1-bedroom apartment in Carmel with WiFi, AC
Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$859
HK$2,147 total
includes taxes & fees
8 Feb - 9 Feb
Elegant Hideaway with Free Parking
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 reviews)
"Great location"
United States
Jordan S.
The price is HK$738
HK$1,054 total
includes taxes & fees
8 Feb - 9 Feb
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Living area

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
The price is HK$1,555
HK$2,904 total
includes taxes & fees
8 Feb - 9 Feb
Luxury 3BR Family Home Game Room Parking
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$914
HK$3,331 total
includes taxes & fees
10 Feb - 11 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,469
HK$2,378 total
includes taxes & fees
8 Feb - 9 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Free WiFi

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is HK$1,555
HK$2,904 total
includes taxes & fees
8 Feb - 9 Feb
Two Wash
Desk, free WiFi, bed sheets

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

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is HK$894
HK$1,996 total
includes taxes & fees
17 Feb - 18 Feb
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Living area

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
The price is HK$1,172
HK$2,553 total
includes taxes & fees
8 Feb - 9 Feb
Uscale 2BR Escape in the Heart of NYC
Fridge, microwave, oven, stovetop

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is HK$1,222
HK$2,205 total
includes taxes & fees
10 Feb - 11 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,231
HK$2,564 total
includes taxes & fees
17 Feb - 18 Feb
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (13 reviews)
"Absolutely perfect location--so lovely to walk to restaurants, ice cream, views, etc. Would definitely stay here again."
United States
joelle a.
The price is HK$938
HK$1,645 total
includes taxes & fees
15 Feb - 16 Feb
Piermont Oasis
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

Best Western Fort Lee

Best Western Fort Lee

10/10 Excellent
"Staff was nice and room was nice and clean, breakfast was good also. "
Bianca 1-night trip
Posted 2 days ago
Best Western Fort Lee

Find out more about Pleasantville

Search for holiday rentals in Pleasantville on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasantville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pleasantville!

Frequently asked questions

Can I find a holiday rental in Pleasantville?

Yes, there are holiday rentals close to the most popular sights in Pleasantville, 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?

Waterfront Retreat Center for Health & Wellness: This holiday home rental outside of Pleasantville is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

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.