Pleasantville Holiday Rentals

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Holiday Rentals in Pleasantville

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (17)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$292
includes taxes & fees
26 Oct - 27 Oct
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
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 traveller
The price is AU$326
includes taxes & fees
26 Oct - 27 Oct
Piermont Oasis
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 AU$365
includes taxes & fees
31 Oct - 1 Nov
Charming 1-bedroom apartment in Carmel with WiFi, AC
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is AU$342
includes taxes & fees
21 Oct - 22 Oct
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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 AU$211
includes taxes & fees
21 Oct - 22 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
The Mansion Hotel-style
4.5 star property
The price is AU$250
includes taxes & fees
21 Oct - 22 Oct
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 AU$285
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom retreat minutes from West Point!
Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!
6.8 out of 10, (15)
"It was very clean and in a great area. "
United States
Kyle
The price is AU$286
includes taxes & fees
20 Oct - 21 Oct
Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!
'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 AU$473
includes taxes & fees
27 Oct - 28 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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
Cozy Apartment to Relax - Apartment "B"
2.0 star property
The price is AU$501
includes taxes & fees
22 Oct - 23 Oct
Cozy Apartment to Relax - Apartment "B"
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 AU$449
includes taxes & fees
30 Oct - 31 Oct
Guesthouse at Norwalk Inn
Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (6)
"Very nice! Easy to work with and house was what we expected. "
United States
Jack P.
The price is AU$619
includes taxes & fees
16 Nov - 17 Nov
Seabreeze at the beach west beach Stamford ct.
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 AU$572
includes taxes & fees
22 Oct - 23 Oct
Modern Luxe 1BR Apt in Downtown Stamford
Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (19)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is AU$402
includes taxes & fees
22 Oct - 23 Oct
Walk to WP Gate + Free Parking!
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
9.2 out of 10, Wonderful, (9)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AU$420
includes taxes & fees
25 Oct - 26 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AU$755
includes taxes & fees
29 Oct - 30 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
price will make you book twice , luxury living
10.0 out of 10, Exceptional, (1)
"We had a great stay! Room was very open and clean and our host was friendly and welcoming! "
United States
Sage
The price is AU$282
includes taxes & fees
23 Oct - 24 Oct
price will make you book twice , luxury living
New Modern Apartment
10.0 out of 10, Exceptional, (4)
"great place to stay at absolutely comfortable and great neighborhood!"
United States
fransheska r.
The price is AU$365
includes taxes & fees
12 Nov - 13 Nov
New Modern Apartment
Apartment B - Next to Hiking Trail - Back Entrance
2.0 star property
The price is AU$514
includes taxes & fees
20 Oct - 21 Oct
Apartment B - Next to Hiking Trail - Back Entrance
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

Find out more about Pleasantville

Everything you need to know about Pleasantville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pleasantville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasantville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasantville holiday rentals we have selected for you start as low as AU$211 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville holiday 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 holiday.

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 holiday rental in Pleasantville?

Yes, there are holiday rentals close to the most popular sights in Pleasantville, 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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Pleasantville is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday 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 wider area, you’ll find Jacob Burns Film Center Media Arts Lab and Union Church of Pocantico Hills.

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.