Pleasantville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Pleasantville

The Mansion Hotel-style
4.5 star property
7.6 out of 10, Good, (5)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is ¥21,514
¥24,741 total
includes taxes & fees
Nov 2 - Nov 3
The Mansion Hotel-style
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ¥17,416
¥29,597 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom retreat minutes from West Point!
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (19)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is ¥11,641
¥30,431 total
includes taxes & fees
Nov 2 - Nov 3
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ¥18,489
¥39,002 total
includes taxes & fees
Oct 31 - Nov 1
Charming 1-bedroom apartment in Carmel with WiFi, AC
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
United States
Scott G.
The price is ¥22,065
¥62,971 total
includes taxes & fees
Nov 5 - Nov 6
House on the Babbling Brook- Quiet 2BR + King Bed!
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is ¥17,195
¥45,874 total
includes taxes & fees
Nov 3 - Nov 4
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
8.0 out of 10, Very Good, (17)
"Great place great location"
United States
Daquan H.
The price is ¥14,380
¥20,519 total
includes taxes & fees
Nov 2 - Nov 3
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Cozy Cottage with Grill | Walk to Lake
9.8 out of 10, Exceptional, (22)
"Our second time staying at the cottage and we love it so much. So comfortable. So close to the lake, and just fabulous!"
United States
CarlyS
The price is ¥29,308
¥76,656 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Cottage with Grill | Walk to Lake
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (5)
"Lovely little home in Stamford."
United States
Pat A.
The price is ¥23,967
¥50,693 total
includes taxes & fees
Nov 7 - Nov 8
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (4)
"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 ¥24,286
¥40,112 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Piermont Oasis
10.0 out of 10, Exceptional, (5)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
United States
Anonymous traveler
The price is ¥18,260
¥31,862 total
includes taxes & fees
Nov 5 - Nov 6
Piermont Oasis
3BR West Point Retreat-3min to Back Gate+ King Bed
9.0 out of 10, Wonderful, (2)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
The price is ¥17,195
¥66,623 total
includes taxes & fees
Nov 3 - Nov 4
3BR West Point Retreat-3min to Back Gate+ King Bed
Cozy Private Share Room
2.0 star property
6.8 out of 10, (17)
"I loved the area. Instructions were very clear. House was clean and kept clean 100% of the time. Privacy was kept the entire time. "
United States
Marvin
Cozy Private Share Room
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
2.0 star property
The price is ¥12,174
¥17,406 total
includes taxes & fees
Oct 31 - Nov 1
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
Private Suite
2.0 star property
The price is ¥17,043
¥30,110 total
includes taxes & fees
Nov 8 - Nov 9
Private Suite
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very Good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ¥42,030
¥48,335 total
includes taxes & fees
Nov 6 - Nov 7
Guesthouse at Norwalk Inn
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
10.0 out of 10, Exceptional, (5)
"We had an excellent stay! Our hosts were kind and helpful. The home was modern and very well kept, very clean. I would highly recommend this location and home to anyone traveling in the area."
United States
Suzanne A.
The price is ¥19,925
¥45,938 total
includes taxes & fees
Nov 3 - Nov 4
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Modern Luxe 1BR Apt in Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ¥20,543
¥56,113 total
includes taxes & fees
Nov 3 - Nov 4
Modern Luxe 1BR Apt in Downtown Stamford
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (123)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ¥28,608
¥46,824 total
includes taxes & fees
Nov 9 - Nov 10
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"Maria is a wonderful host. We enjoyed our stay. Thank you."
United States
Jack B.
The price is ¥18,670
¥43,166 total
includes taxes & fees
Nov 6 - Nov 7
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pleasantville Hotel Reviews

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 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 of 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 Union Church of Pocantico Hills.

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.