
Holiday rentals in Pleasantville
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pleasantville
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pleasantville holiday rentals
Other great holiday rentals in Pleasantville
Top guest favourite

Treehouse in Wallkill
4.99 out of 5 average rating, 316 reviewsThe Treecastle at the Roundhouse Homestead
ShannonRating, 5 stars2 days ago
Absolutely beyond pleased with our stay at the tree castle. Such a magical little getaway! The hosts are spectacular with communication and meeting your every need, and went above and beyond with supplying creature comforts and fresh baked goods (that are to die for!). The tree castle was so clean and stayed nice and cool despite the summer heat, even the outdoor bathroom was sparkly clean and a pleasure to use. We would come to stay again in a heartbeat, thank you for everything Dan and Melissa! And thank you for the delicious honey and letting us meet your chickens!! 🐓🐝💕💐
Top guest favourite

Home in Valhalla
5 out of 5 average rating, 15 reviewsValhalla Home
MichaelRating, 5 stars6 days ago
A perfect spot for visiting Westchester. Easy access to the City and easy access to Tarrytown etc... The place was great. A big space in a super cool 50s era house with super modern amenities.

Guest suite in Pleasantville
4.65 out of 5 average rating, 57 reviewsEntire Pleasant Private Studio APT
MarkRating, 5 stars8 months ago
Sue’s unit was the perfect place for me to stay for a weekend wedding in the town center of Pleasantville. Very convenient parking and access, clear instructions, and great communication. Nice bed and bathroom. Easy walk into town, especially nice with the turning leaves.
Guest favourite

Guest suite in Croton-on-Hudson
4.88 out of 5 average rating, 16 reviewsMountain Edge: Spacious Suite
NefretyreeRating, 5 stars1 week ago
We stayed here after a long night of travel. It was a beautiful location on the way to our final destination. It was peaceful and easy to sleep during the day. The air conditioning was nice. It was cool when we arrived and felt very cozy. The queen bed was incredibly comfortable. It was perfect for what we needed, but we wish we could have been awake longer to enjoy the scenery longer.
Top guest favourite

Private room in Sleepy Hollow
4.98 out of 5 average rating, 110 reviewsAleida'house on beautiful town.
BeatriceRating, 5 stars1 month ago
My 5 night stay at Aleida’s in Tarrytown was fantastic. Aleida was a very helpful and friendly host, I felt very at home with her. Aleida always replied to any questions promptly. The house is in a great location, only about 5 minutes walk from the station. It is also very close to the river Hudson, and you can do a beautiful riverside walk to see the Tappan Zee bridge and Sleepy Hollow lighthouse. As a woman travelling on my own, I felt very safe in Tarrytown. A couple of times I got the train back from Grand Central late at night, and I always felt comfortable walking back from Tarrytown station to the house. I also felt safe walking around the town in the evening. It’s a very safe and friendly place, and only a 50 minute train to Grand Central. There are plenty shops and things to do in the town too. I would recommend booking a show at the historic Tarrytown Music Hall - it’s really special. I will miss my chats over breakfast with Aleida and would love to come back one day.

Home in Philipstown
5 out of 5 average rating, 9 reviewsArkadia House Mid-century retreat with pool & view
AriRating, 5 stars71 months ago
Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.
Guest favourite

Guest suite in Katonah
4.9 out of 5 average rating, 77 reviewsComfy Peaceful Retreat
LyndaRating, 5 stars5 days ago
I stayed at Susan’s place in Katonah for just one night, and it was a truly lovely experience. The bedroom and private bathroom were spotless, cozy, and thoughtfully prepared—perfect for a peaceful stay tucked in the woods, yet only a few minutes from downtown Katonah’s charming shops, restaurants, and cafes. Susan was warm and welcoming from the start, offering me a bagel, cream cheese, and orange juice upon arrival—a kind gesture that meant a lot since I hadn’t had breakfast. She also graciously allowed me to check in early, which made my day much easier. The space is small but has everything you need: a super comfortable bed and pillows, tea and coffee, fresh water, fruit, cookies, and even fresh flowers on the table. It felt so inviting and cared for. I would absolutely stay again. Thank you, Susan!
Guest favourite

Home in White Plains
5 out of 5 average rating, 5 reviewsThe Washington Place: convenient, spacious, comfy
JaneRating, 5 stars6 days ago
Jose and Amy are terrific hosts - very responsive to questions and their space is very large, clean, quiet, with gorgeous floors, a large bathroom with plush cotton towels, and a fully equipped modern kitchen including New England brand ground coffee (not the pre-filled pods) to use in the Keurig machine. Everything was immaculate. Loved the comfy sofas and the huge TV in the living room. My husband and I would definitely stay there again.
Quick stats about holiday rentals in Pleasantville
Total rentals
10 properties
Nightly prices starting at
₹3,463 before taxes and fees
Total number of reviews
660 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Self check-in, Gym and BBQ grill
Local attractions
Wood & Fire, Southern Table kitchen & Bar and The Pleasantville Diner
Destinations to explore
- East River Holiday rentals
- Plainview Holiday rentals
- New York Holiday rentals
- Long Island Holiday rentals
- Hudson Valley Holiday rentals
- The Hamptons Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo