Pleasantville Vacation Rentals

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Check prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Pleasantville vacation rentals

Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.4 out of 10, Very Good, (20)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is ￥20,053
￥23,061 total
includes taxes & fees
Dec 16 - Dec 17
The Mansion Hotel-style
Lobby
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (79)
"It was great"
United States
Natalie
The price is ￥18,697
￥21,502 total
includes taxes & fees
Dec 18 - Dec 19
Stamford Suites
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.4 out of 10, Very Good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ￥41,297
￥47,492 total
includes taxes & fees
Dec 29 - Dec 30
Guesthouse at Norwalk Inn
Apartment (1 Bedroom) | 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 ￥18,697
￥42,872 total
includes taxes & fees
Dec 22 - Dec 23
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury House | Private kitchen
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 ￥31,006
￥50,113 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Spacious 3BR Luxe Escape near NYC
Luxury House | 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 ￥31,006
￥50,112 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Spacious 3BR Luxe Escape near NYC
Luxury Villa, Garden View | 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 ￥70,115
￥105,981 total
includes taxes & fees
Dec 16 - Dec 17
Luxury NYC Home with Free Parking for 12
Luxury Villa, Patio | Private kitchen
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 ￥69,959
￥101,483 total
includes taxes & fees
Dec 16 - Dec 17
Luxury 5 BR Home Free Parking
Luxury Apartment | Free WiFi
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 ￥31,006
￥57,749 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Prime Luxe 3-BR NYC - Free Parking
Terrace/patio
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 traveler
The price is ￥38,797
￥58,829 total
includes taxes & fees
Jan 12 - Jan 13, 2026
3BR Prime Luxury near NYC w Arcade Room
House | 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 ￥64,305
￥145,156 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Luxury House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop
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 ￥70,115
￥93,867 total
includes taxes & fees
Dec 16 - Dec 17
Modern Comfort in the Heart of NYC
Luxury House | Living area | Flat-screen TV
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 ￥58,740
￥81,139 total
includes taxes & fees
Dec 16 - Dec 17
Luxury NY Home 3BR with Easy Parking
Apartment (1 Bedroom) | Interior
Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan
3.0 star property
West Norwalk
The price is ￥34,278
￥55,311 total
includes taxes & fees
Dec 16 - Dec 17
Gold Coast Getaway! Upscale Apt Near New Canaan
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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Clean, attractive hotel and courteous staff. Note the restaurant is only open for breakfast and dinner "
Christine 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Nanuet

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
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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 vacation rental in Pleasantville?

Yes, we give you a choice of vacation rentals close to popular attractions in Pleasantville, 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?

3BR Prime Luxury near NYC w Arcade Room: This vacation home rental outside Pleasantville is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation 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 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.