Pleasantville Holiday Rentals

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Check prices for these dates

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Pleasantville holiday rentals

Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$1,976
HK$2,273 total
includes taxes & fees
21 Dec - 22 Dec
Guesthouse at Norwalk Inn
Living area
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very good, (21)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is HK$926
HK$1,065 total
includes taxes & fees
27 Dec - 28 Dec
The Mansion Hotel-style
Dining
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is HK$3,501
HK$5,292 total
includes taxes & fees
20 Jan - 21 Jan 2026
Luxury NYC Home with Free Parking for 12
Dining
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
The price is HK$3,501
HK$4,688 total
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Comfort in the Heart of NYC
Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$934
HK$2,141 total
includes taxes & fees
4 Jan - 5 Jan 2026
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Private kitchen
JayZero

JayZero

JayZero
2.0 star property
Bryn Mawr
The price is HK$770
HK$2,021 total
includes taxes & fees
5 Jan - 6 Jan 2026
JayZero
Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is HK$1,548
HK$2,503 total
includes taxes & fees
19 Jan - 20 Jan 2026
Spacious 3BR Luxe Escape near NYC
Private kitchen
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveller
The price is HK$1,937
HK$2,938 total
includes taxes & fees
19 Jan - 20 Jan 2026
3BR Prime Luxury near NYC w Arcade Room
Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is HK$1,548
HK$2,503 total
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC
Free WiFi
Two Wash

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is HK$1,548
HK$2,892 total
includes taxes & fees
20 Jan - 21 Jan 2026
Two Wash
Exterior
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (81)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is HK$859
HK$988 total
includes taxes & fees
21 Dec - 22 Dec
Stamford Suites
5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
The price is HK$2,981
HK$6,985 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Dining
Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$1,548
HK$2,884 total
includes taxes & fees
4 Jan - 5 Jan 2026
Prime Luxe 3-BR NYC - Free Parking
Living area
Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
The price is HK$5,058
HK$6,818 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury 5 BR Home Free Parking
Private kitchen
Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$856
HK$2,138 total
includes taxes & fees
4 Jan - 5 Jan 2026
Elegant Hideaway with Free Parking
Free WiFi
Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is HK$856
HK$2,117 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe 1BR Oasis - Prime NY Stay
Interior
Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$1,548
HK$2,930 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury 3BR Home Game Room Free Parking
Free WiFi
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
The price is HK$1,548
HK$2,892 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury 3BR Family Home Game Room Parking
Living area
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking
3.0 star property
Southeast Yonkers
3.0 out of 10, (4)
"There was nothing luxury about this place. Please dont let the pictures fool you and its non refundable. Communication is horrible. They even tried charging cleaning fee for a dirty house, i took a total loss and just stayed at hotels "
United States
Jose
The price is HK$2,933
HK$4,052 total
includes taxes & fees
21 Dec - 22 Dec
Luxury NY Home 3BR with Easy Parking
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

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

10/10 Excellent
"Staff was very nice and the housekeepers as well "
mariely 4-night trip
Posted 3 days ago
Hampton Inn & Suites Yonkers

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:

  • View our selection of featured holiday rentals in Pleasantville
  • Use the map to find apartments and other holiday homes in the Pleasantville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pleasantville while they last

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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside Pleasantville is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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.