A calm lake surrounded by autumn-colored trees reflecting in the water.

Pleasantville Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Pleasantville holiday rentals

Private kitchen

1. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$1,405
HK$2,776 total
includes taxes & fees
6 Sept - 7 Sept
Elegant Hideaway with Free Parking
Interior

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is HK$1,114
HK$2,274 total
includes taxes & fees
19 Aug - 20 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Property grounds

3. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$861
HK$1,211 total
includes taxes & fees
16 Aug - 17 Aug
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Property grounds

4. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (20 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$941
HK$1,643 total
includes taxes & fees
7 Sept - 8 Sept
Piermont Oasis
Living area

5. NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is HK$854
HK$2,125 total
includes taxes & fees
18 Aug - 19 Aug
NY Luxury Apt Free Parking in PRIME Area
Living area

6. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"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...
United States
Jorge
The price is HK$3,883
HK$5,610 total
includes taxes & fees
30 Aug - 31 Aug
Luxury NYC Home Game Room Free Parking
Interior

7. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is HK$1,687
HK$2,149 total
includes taxes & fees
9 Aug - 10 Aug
1BR Queen near NYC | Trails, Biking & Sauna Bliss
1 bedroom, iron/ironing board, free WiFi, bed sheets

8. 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
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is HK$741
HK$1,058 total
includes taxes & fees
10 Aug - 11 Aug
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
5 bedrooms

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is HK$6,032
HK$10,503 total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Smart TV

10. Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is HK$4,229
HK$7,062 total
includes taxes & fees
9 Aug - 10 Aug
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
Offices

11. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is HK$1,130
HK$2,444 total
includes taxes & fees
9 Aug - 10 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Smart TV, video games, DVD player, books

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

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is HK$2,109
HK$3,793 total
includes taxes & fees
10 Aug - 11 Aug
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Exterior

13. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (153 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is HK$1,054
HK$1,213 total
includes taxes & fees
9 Aug - 10 Aug
Stamford Suites
Property grounds

14. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
The price is HK$1,561
HK$2,826 total
includes taxes & fees
8 Sept - 9 Sept
Garden Loft with Patios & Green Space · Westchester Retreat
3 bedrooms, iron/ironing board, Internet, bed sheets

15. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is HK$3,883
HK$6,523 total
includes taxes & fees
6 Sept - 7 Sept
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
TV

16. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is HK$1,726
HK$3,239 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Dining

17. Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is HK$1,177
HK$2,334 total
includes taxes & fees
24 Aug - 25 Aug
Romantic Hide Out
Property grounds

18. 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
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,671
HK$3,177 total
includes taxes & fees
8 Sept - 9 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Outdoor banquet area

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.6 out of 10, Excellent, (8 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$5,335
HK$9,525 total
includes taxes & fees
10 Aug - 11 Aug
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Dining

20. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is HK$3,177
HK$4,943 total
includes taxes & fees
12 Aug - 13 Aug
Luxury NYC Home with Free Parking for 12
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

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent
"yes all good"
GRAZIELLA 3-night trip
Posted 2 hours ago
Sleepy Hollow Hotel, a Dolce by Wyndham

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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  • 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 in Pleasantville close to Jacob Burns Film Center Media Arts Lab, 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Pleasantville is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

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.