Holiday rentals in Pleasantville

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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 reviews

The 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 reviews

Valhalla 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 reviews

Entire 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 reviews

Mountain 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 reviews

Aleida'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 reviews

Arkadia 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 reviews

Comfy 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 reviews

The 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