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Westchester County Holiday Rentals

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Our top choices for Westchester County holiday rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is S$1,064
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

2. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is S$452
includes taxes & fees
6 Oct - 7 Oct
Elegant Hideaway with Free Parking
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

3. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is S$770
includes taxes & fees
6 Oct - 7 Oct
Spacious 3BR Luxe Escape near NYC
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

4. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is S$1,498
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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 Westchester County Hotel Reviews

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Room was very clean and the estate is very pretty. The breakfast had pretty much anything you could think of and was good quality. Parking was a little tricky but there were weddings both days we stayed"
Michelle 2-night trip
Posted 2 hours ago
Tarrytown House Estate