Pleasantville Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Pleasantville holiday rentals

Property grounds

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,049
HK$2,144 total
includes taxes & fees
13 Mar - 14 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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, (132 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,471
HK$2,381 total
includes taxes & fees
12 Mar - 13 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,281
HK$3,795 total
includes taxes & fees
12 Mar - 13 Mar
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,760
HK$3,266 total
includes taxes & fees
12 Mar - 13 Mar
Contemporary Cozy Cottage
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$739
HK$1,055 total
includes taxes & fees
14 Mar - 15 Mar
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Property grounds

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is HK$1,267
HK$3,112 total
includes taxes & fees
12 Mar - 13 Mar
Seabreeze at the beach west beach Stamford ct.
Offices

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)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is HK$1,127
HK$2,414 total
includes taxes & fees
16 Mar - 17 Mar
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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$1,056
HK$2,179 total
includes taxes & fees
12 Mar - 13 Mar
Charming 1-bedroom apartment in Carmel with WiFi, AC
Living area

Cheerful Home in Yonkers NY

Cheerful Home in Yonkers NY
Lincoln Park
7.6 out of 10, Good, (4 reviews)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is HK$1,955
HK$4,604 total
includes taxes & fees
13 Mar - 14 Mar
Cheerful Home in Yonkers NY
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$587
HK$2,017 total
includes taxes & fees
12 Mar - 13 Mar
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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$748
HK$1,493 total
includes taxes & fees
7 Apr - 8 Apr
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

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$859
HK$1,207 total
includes taxes & fees
19 Mar - 20 Mar
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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$845
HK$2,873 total
includes taxes & fees
17 Mar - 18 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
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$1,099
HK$2,241 total
includes taxes & fees
18 Mar - 19 Mar
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,721
HK$3,051 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Interior

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$1,150
HK$2,945 total
includes taxes & fees
24 Mar - 25 Mar
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90 reviews)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$1,024
HK$2,353 total
includes taxes & fees
12 Mar - 13 Mar
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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
9.8 out of 10, Exceptional, (6 reviews)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is HK$884
HK$3,295 total
includes taxes & fees
12 Mar - 13 Mar
Sleek Escape: Modern 3 BR- 4 Min from West Point !
TV, fireplace, books, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
The price is HK$2,870
HK$6,795 total
includes taxes & fees
12 Mar - 13 Mar
New Beach Home near Stamford Downtown/Shippan
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

6/10 Okay
"Internet was not free. You have to be a member "
Shakeema 3-night trip
Posted 3 hours 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:

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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 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Pleasantville is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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.