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Compare 287 Vacation Homes in Pleasantville with updated reviews, rates, and availability.

Cozy Indoor Hot Tub, Fire Pit & Game Room

9.6 out of 10, Exceptional, (4)
"It was a wonderdul and relaxing stay with the family"
Cozy Indoor Hot Tub, Fire Pit & Game Room

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (56)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (94)
"I cannot say enough good things about Deirdre's beautiful home and how grateful my family was to be able to stay here during our visit to Stamford. The house is perfect for a family with younger kids; they were so excited to have their very own play room! The rooms and bathrooms are well equipped with everything you might need, as was the kitchen. Deirdre in particular was so communicative and helpful with all of our questions. We very much hope to have an excuse to stay here again!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Cozy and beautiful house

10.0 out of 10, Exceptional, (20)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (14)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!

Up-to-date Home w/ Pool, Playground & Fireplace!

10.0 out of 10, Exceptional, (1)
Up-to-date Home w/ Pool, Playground & Fireplace!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (23)
"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "
Updated Home w/ Patio Half Mile to West Point

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (38)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

9.6 out of 10, Exceptional, (49)
"We stayed here with our 3 dogs between Christmas and New Years. It is in a gorgeous neighborhood of sprawling estate homes. This property had tons of room to spread out. The yard is HIGE and completely fenced in. The rooms are decorated with the photography work of the owner and other interesting pieces. Plenty to do on site and not too far from the city. Lisa was great and even let our dogs out to potty so we could relax traveling into the city for a show and dinner. We would love to...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (11)
"Host was very accommodating and easy to communicate with!"
The price is AED 1,194
AED 1,939 total
includes taxes & fees
24 Feb - 25 Feb
Luxury 3Bed Private Apartment Near Manhattan

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

2.0 star property
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (25)
"Akuvi is an outstanding host. Prior to and during our stay he was immediately responsive to all of the messages/requests I sent him. The listing on VRBO is accurate and if you look at the description and pictures you'll get exactly what you're looking at"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Quiet apartment with balcony parking walking distance to church and cross county

2.0 star property
10.0 out of 10, Exceptional, (1)
"Host is kind and welcoming. The place is in a very quiet neighborhood. Plenty of street parking. 25 min from nyc. Highly recommend "
Quiet apartment with balcony parking walking distance to church and cross county

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
Waterview House Walking Distance from Cove Beach

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is AED 1,212
AED 2,770 total
includes taxes & fees
24 Feb - 25 Feb
New Beach Home near Stamford Downtown/Shippan

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is AED 918
AED 1,363 total
includes taxes & fees
24 Feb - 25 Feb
Contemporary Cozy Cottage

Marvelous 4-bedroom house in Woodlawn Heights, family friendly.

10.0 out of 10, Exceptional, (3)
"This home was perfect for us and our group of friends whom were flying in to surprise a local Bronx friend for his 40th. The bedrooms were great and overall clean and decorated nicely. The location of this home was close to everything from walking distance to a 15-20min drive. We enjoyed the front porch and backyard for a cocktail or two. Not to mention that the house manager was great on communication. Thank you and we highly recommend!"
Marvelous 4-bedroom house in Woodlawn Heights, family friendly.

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house and right outside West Point"
The price is AED 1,653
AED 2,768 total
includes taxes & fees
24 Feb - 25 Feb
West Point Family Retreat, 5 min walk to Thayer!
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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Other property types in Pleasantville

Global Luxury Suites White Plains

3.5 star property
7.0 out of 10, Good, (28)
"I was very impressed with this "hotel". It is more of an AirBB as your unit is an apartment in an apartment building with permant residents. It comes nicely furnished, including basic kitchen essentials (like service for four, pots and pans, coffee maker, etc). All of the amenities are modern, and the in-unit washer dryer is a huge plus. I also really appreciated some of the welcome gifts, including some coffee/tea, laundry detergent, and your basic hygiene essentials. Property communicates...
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is AED 621
AED 714 total
includes taxes & fees
8 Mar - 9 Mar
Stamford Suites

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is AED 617
AED 900 total
includes taxes & fees
24 Feb - 25 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.