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

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

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (32)
"Hot tub was awesome. Near bear mountain, also relatively easy train access to NYC across bridges."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (21)
"The perfect location just one hour north of New York City to host a weekend leadership summit."
Modern, Magical Woodsy Escape 1 Hour From NYC

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

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"It was a quick trip to see woman’s army basketball game. It was an excellent stay and excellent accommodations. "
The price is SAR 938
SAR 1,410 total
includes taxes & fees
19 Mar - 20 Mar
Contemporary Cozy Cottage

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (12)
"I enjoyed everything about this property except the description stated there were 2 steps to enter property. It failed to metro the 15 stairs once you opened the door. My aunt struggled with this so be aware when booking this property if you have accessibility needs. "
Glen Cove Home: Walk to Boardwalk + Dining!

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.2 out of 10, Wonderful, (5)
"Great location, quite dead end. Excellent value, we had a very comfortable stay.Walking distance to the station for Metro North into NYC. Great deli just around the corner. Responsive hosts, will gladly use again!! "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (38)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

Charming 3-bedroom house with AC, WiFi in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (15)
"The home was clean and the area is beautiful! It was a wonderful experience staying in a historic home and the owners were fantastic!"
Historic Hideaway with Lake Access!

Chill Vibes & Luxe Living: Pool, Playground & Fire

10.0 out of 10, Exceptional, (1)
Chill Vibes & Luxe Living: Pool, Playground & Fire

'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!

Modern Farmhouse Walking Distance to West Point

9.2 out of 10, Wonderful, (7)
"A second stay at this home. The location truly can't be beat at this cozy historic home. The home has lots of charm from the wood floors, to the covered front porch, to the nice backyard. Restaurants and Pubs are a quick walk, a wine store is a few paces away for that relaxing end-of-night glass. I previously reviewed the place and noted a lack of a baking sheet (as did a prior reviewer). We purchased one for the kitchen on our stay as well as a stock pot - cold night air called for a pot...
Modern Farmhouse Walking Distance 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.

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 SAR 1,219
SAR 1,962 total
includes taxes & fees
13 Mar - 14 Mar
Luxury 3Bed Private Apartment Near Manhattan

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (19)
"This property worked out perfectly for our family group. We needed a home that could accommodate 14 people across 3 generations comfortably and this property definitely addressed our needs. The home is huge, very well laid out, and well appointed. It was very clean and functional. It had a nice homey feel and wasn't cluttered with the owner's things. Some specifics:• There are a LOT of spacious bedrooms. Most have en-suite bathrooms, which is great.• The main level is well laid out and has lots...
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

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 SAR 1,238
SAR 2,833 total
includes taxes & fees
16 Mar - 17 Mar
New Beach Home near Stamford Downtown/Shippan

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (95)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
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)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is SAR 634
SAR 729 total
includes taxes & fees
26 Mar - 27 Mar
Stamford Suites

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (15)
"Perfect location. Great service. Amenities pretty cool "
Luxury Apartments by Hyatus at The Asher
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.