Holiday rentals in Pound Ridge

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Top-rated holiday rentals in Pound Ridge

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

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

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.

2–9 Sep

₹11,122 per night
Guest favourite

Guest house 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

25 Sep – 2 Oct

₹23,509 per night
Guest favourite

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.

22–29 Jun

₹19,352 per night

Popular amenities for Pound Ridge holiday rentals

Other great holiday rentals in Pound Ridge

Guest favourite

Home in Stamford

4.98 out of 5 average rating, 130 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

13–20 Apr

₹8,199 per night
Guest favourite

Home in Stamford

4.97 out of 5 average rating, 217 reviews

Midcentury Modern ZenHouse Sculptor Studio

15–22 Nov

₹35,854 per night
Guest favourite

Guest house in Pound Ridge

4.95 out of 5 average rating, 60 reviews

A Lovely Cottage in the Woods

19–26 Apr

₹19,723 per night
Guest favourite

Home in Pound Ridge

5.0 out of 5 average rating, 17 reviews

Private farm cottage +hiking

15–22 Jun

₹17,295 per night
Guest favourite

Guest suite in Wilton

5.0 out of 5 average rating, 24 reviews

Guest suite with private enter

30 Apr – 7 May

₹7,830 per night
Guest favourite

Flat in Stamford

5.0 out of 5 average rating, 49 reviews

Standalone Cottage surrounded by woods

8–15 Oct

₹8,469 per night
Guest favourite

Guest house in Pound Ridge

5.0 out of 5 average rating, 14 reviews

Renovated guesthouse on private 7 acre property

21–28 Nov

₹22,366 per night
Guest favourite

Cottage in Bedford

5.0 out of 5 average rating, 57 reviews

Clover Cottage

16–23 Dec

₹16,336 per night
Guest favourite

Guest suite in Stamford

4.97 out of 5 average rating, 35 reviews

Retreat in North Stamford

31 Jul – 7 Aug

₹11,799 per night
Superhost

Cottage in Pound Ridge

4.8 out of 5 average rating, 50 reviews

Private Cottage in Pound Ridge

2–9 Jan

₹19,680 per night
Guest favourite

Guest house in Bedford

5.0 out of 5 average rating, 13 reviews

Red Coat Cottage

26 Jul – 2 Aug

₹25,431 per night
Guest favourite

Guest suite in Wilton

4.9 out of 5 average rating, 99 reviews

Serene Pond Views charming private patio…

17–24 Apr

₹10,495 per night

Destinations to explore