Pleasantville Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pleasantville vacation rentals

A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

1. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveler
$111 nightly
The price is $127
Nov 10 - Nov 11
Total with taxes and fees
1 Queen Bed | Smoking
A stone staircase leading to a house with a stone wall and a metal gate.

2. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$343 nightly
The price is $392
Nov 10 - Nov 11
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

3. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveler
$114 nightly
The price is $130
Nov 10 - Nov 11
Total with taxes and fees
1 King Bed | Non-Smoking
A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

4. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveler
$116 nightly
The price is $133
Nov 10 - Nov 11
Total with taxes and fees
2 Full Beds | Non-Smoking
A hotel room with a bed, a desk, and a chair.

5. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
8.0 out of 10, Very good, (6 reviews)
$111 nightly
The price is $127
Nov 10 - Nov 11
Total with taxes and fees
1 Queen Bed | Non-Smoking
A wooden staircase leading to a small shed with a slanted roof, surrounded by dense greenery and a stone wall.

6. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Megan D.
$175 nightly
The price is $195
Nov 16 - Nov 17
Total with taxes and fees
Piermont Oasis
A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
$765 nightly
The price is $781
Nov 16 - Nov 17
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A nighttime view of a residential street with houses, trees, and parked cars.

8. 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, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
$312 nightly
The price is $357
Nov 12 - Nov 13
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$947 nightly
The price is $1,054
Nov 16 - Nov 17
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

10. '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, (9 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.
$371 nightly
The price is $424
Nov 19 - Nov 20
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

11. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
$265 nightly
The price is $295
Nov 15 - Nov 16
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A living room with a sofa, a coffee table, a lamp, a staircase, and a bookshelf.

12. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
$312 nightly
The price is $356
Nov 16 - Nov 17
Total with taxes and fees
Historic, private riverfront cottage in peaceful Greenwich
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

13. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
$164 nightly
The price is $189
Nov 10 - Nov 11
Total with taxes and fees
Stamford Suites
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

14. 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
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
$105 nightly
The price is $123
Nov 10 - Nov 11
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A room with large windows overlooking a lake and greenery.

15. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
$289 nightly
The price is $330
Nov 10 - Nov 11
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

16. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$294 nightly
The price is $297
Nov 10 - Nov 11
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

17. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
$220 nightly
The price is $252
Nov 10 - Nov 11
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
An outdoor patio with a fire pit, green chairs, and a table.

18. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (13 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
$266 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A wooden staircase leading to a gazebo in a forested area with a metal railing.

19. 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
8.6 out of 10, Excellent, (7 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.
$245 nightly
The price is $280
Nov 10 - Nov 11
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A modern living room with a sofa, a coffee table, and a bar stool.

20. 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.
$256 nightly
The price is $293
Nov 20 - Nov 21
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne

10/10 Excellent

The room was very clean and the hotel itself looked very clean. Beds were comfortable and the room was very spacious. I would definitely recommend this hotel to anyone staying in this area.
United States
Lorena
Reviewed December 27, 2023
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Find out more about Pleasantville

Everything you need to know about Pleasantville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasantville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasantville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasantville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasantville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasantville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasantville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasantville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Pleasantville?

Yes, we give you a choice of vacation rentals in Pleasantville close to Jacob Burns Film Center Theater, 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?

Modern Luxury Home w GameRoom & Parking: This vacation home rental outside of Pleasantville is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

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.

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