Vacation rentals in Pound Ridge

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Top-rated vacation rentals in Pound Ridge

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

Guest favorite

Apartment in Mount Kisco

4.93 out of 5 average rating, 147 reviews

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

This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Nov 13 – 20

R2,526 ZAR per night
Guest favorite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 111 reviews

Barrett's Sanctuary

Airy, bright guest house with with access to a gunite pool*, patio and expansive backyard for practicing your short game, playing disc golf or other sports. Loft (accessible by spiral staircase) furnished with queen bed. Single bed in alcove off living room. Central air/heat. Washer/dryer. Kitchenette w/ dishwasher. Satellite TV. LR w/ stone fireplace. Minutes to train (1h to Manhattan) and highways. Shopping/restaurants nearby. Delivery available from Seamless, Instacart and more. *Nominal fee

Sep 25 – Oct 2

R5,339 ZAR per night
Guest favorite

Cottage in Pound Ridge

4.93 out of 5 average rating, 168 reviews

Adirondacks in Westchester

Located on quiet, private 5.5 acre estate with swimmable lake, fantastic landscape. Complete privacy, like being in the Adirondacks, but just one hour from NYC. Cottage has high end appliances (Sub-Zero, Miele) with separate road and entrance. Perfect for a getaway from NYC and easily accessible by car or train (Stamford station). Can be combined with Adirondacks in Westchester 2 to provide an additional bedroom in a separate building to accommodate a total of four guests. Excellent wifi.

Feb 24 – Mar 3

R4,395 ZAR per night

Popular amenities for Pound Ridge vacation rentals

Other great vacation rentals in Pound Ridge

Guest favorite

Cottage in Bedford

4.98 out of 5 average rating, 119 reviews

Tudor Cottage In Heart of Bedford

Sep 27 – Oct 4

R9,216 ZAR per night
Guest favorite

Home in Stamford

4.98 out of 5 average rating, 130 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Apr 13 – 20

R1,862 ZAR per night
Guest favorite

Home in Stamford

4.97 out of 5 average rating, 217 reviews

Midcentury Modern ZenHouse Sculptor Studio

May 11 – 18

R6,618 ZAR per night
Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 17 reviews

Private farm cottage +hiking

May 14 – 21

R3,928 ZAR per night
Guest favorite

Guesthouse in Pound Ridge

4.95 out of 5 average rating, 60 reviews

A Lovely Cottage in the Woods

Apr 17 – 24

R4,479 ZAR per night
Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 22 reviews

Guest suite with private enter

Apr 30 – May 7

R1,778 ZAR per night
Guest favorite

Guesthouse in Pound Ridge

5.0 out of 5 average rating, 14 reviews

Renovated guesthouse on private 7 acre property

Nov 18 – 25

R5,079 ZAR per night
Guest favorite

Cottage in Bedford

5.0 out of 5 average rating, 57 reviews

Clover Cottage

Jun 24 – Jul 1

R3,710 ZAR per night
Guest favorite

Apartment in Stamford

5.0 out of 5 average rating, 49 reviews

Standalone Cottage surrounded by woods

Jul 3 – 10

R2,063 ZAR per night
Guest favorite

Guest suite in Stamford

4.97 out of 5 average rating, 35 reviews

Retreat in North Stamford

Jul 28 – Aug 4

R2,680 ZAR per night
Superhost

Cottage in Pound Ridge

4.8 out of 5 average rating, 50 reviews

Private Cottage in Pound Ridge

Dec 31 – Jan 7

R4,469 ZAR per night
Guest favorite

Guesthouse in Bedford

5.0 out of 5 average rating, 13 reviews

Red Coat Cottage

Nov 17 – 24

R5,776 ZAR per night

Destinations to explore