Holiday rentals in Westchester County

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Top-rated holiday rentals in Westchester County

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 377 reviews

Cozy private apartment with Hudson River views

This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.

24–31 May

€ 106 per night
Superhost

Guest suite in Greenwich

4.91 out of 5 average rating, 423 reviews

Charming Greenwich studio, 0.2 miles from train

A charming and spacious "studio" with private entry/exit and very close proximity to Cos Cob train station in Greenwich. Opens to a private back yard. Small library, stone walls, small desk, private hall and bath, and room for 2 (or 3) make it ideal for a weekend getaway with easy access to NYC, Port Chester, Stamford, and New Haven. Five minute walk to Cos Cob village for bakeries, juice and coffee shops, and restaurants. Kid-friendly. Air mattress or crib available upon request.

9–16 May

€ 144 per night
Guest favourite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 705 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

The most booked/popular Airbnb in the area! FREE private driveway. A few blocks to the Hudson River. Super charming, slightly quirky private Shangri-La w/free range chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp, though tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. E-fireplace inside. Firepit outside. Stars galore. 2 patios, yard, hammock, gardens.

30 Jun – 7 Jul

€ 157 per night

Popular amenities for Westchester County holiday rentals

Other great holiday rentals in Westchester County

Guest favourite

Flat in Yonkers

4.94 out of 5 average rating, 210 reviews

Large, relaxing private 1 bedroom apartment.

15–22 Sep

€ 126 per night
Guest favourite

Flat in Dobbs Ferry

4.86 out of 5 average rating, 164 reviews

Private charming Studio efficiency

17–24 Jul

€ 107 per night
Guest favourite

Earthen home in Ossining

4.87 out of 5 average rating, 143 reviews

The Babbling Brook

6–13 Jul

€ 122 per night
Superhost

Flat in Peekskill

4.84 out of 5 average rating, 114 reviews

Little haven by the woods

5–12 Jan

€ 136 per night
Guest favourite

Home in Stamford

4.98 out of 5 average rating, 130 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

13–20 Apr

€ 110 per night
Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 158 reviews

The Little Cottage in the Woods

11–18 Sep

€ 133 per night
Guest favourite

Flat in Mount Kisco

4.93 out of 5 average rating, 147 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

2–9 Sep

€ 131 per night
Guest favourite

Guest suite in Mount Vernon

4.82 out of 5 average rating, 243 reviews

Cozy Studio Getaway w/easy access to NYC/CT

13–20 Jan

€ 99 per night
Guest favourite

Home in Yonkers

4.96 out of 5 average rating, 227 reviews

Conefrey's.

18–25 Aug

€ 110 per night
Guest favourite

Flat in Hastings-on-Hudson

4.99 out of 5 average rating, 86 reviews

30min>Manhattan/on Hudson River/Small town living!

15–22 Jul

€ 113 per night
Guest favourite

Flat in White Plains

4.93 out of 5 average rating, 46 reviews

Clean, convenient, close to station & downtown WP

16–23 Aug

€ 139 per night
Superhost

Home in Hastings-on-Hudson

5.0 out of 5 average rating, 3 reviews

Rivertown Retreat 25 mins to NYC

13–20 May

€ 172 per night

Destinations to explore