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.
Flat in Mount Kisco
4.93 out of 5 average rating, 147 reviewsCozy 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.
13–20 Nov
Guest house in Bedford Hills
4.91 out of 5 average rating, 111 reviewsBarrett'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
Cottage in Pound Ridge
4.93 out of 5 average rating, 168 reviewsAdirondacks 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.
24 Feb – 3 Mar
Holiday rentals for every style
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Popular amenities for Pound Ridge holiday rentals
Other great holiday rentals in Pound Ridge
Cottage in Bedford
4.98 out of 5 average rating, 119 reviewsTudor Cottage In Heart of Bedford
27 Sep – 4 Oct
Home in Stamford
4.98 out of 5 average rating, 130 reviewsSTAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
13–20 Apr
Home in Stamford
4.97 out of 5 average rating, 217 reviewsMidcentury Modern ZenHouse Sculptor Studio
11–18 May
Home in Pound Ridge
5.0 out of 5 average rating, 17 reviewsPrivate farm cottage +hiking
14–21 May
Guest house in Pound Ridge
4.95 out of 5 average rating, 60 reviewsA Lovely Cottage in the Woods
17–24 Apr
Guest suite in Wilton
5.0 out of 5 average rating, 22 reviewsGuest suite with private enter
30 Apr – 7 May
Guest house in Pound Ridge
5.0 out of 5 average rating, 14 reviewsRenovated guesthouse on private 7 acre property
18–25 Nov
Cottage in Bedford
5.0 out of 5 average rating, 57 reviewsClover Cottage
24 Jun – 1 Jul
Flat in Stamford
5.0 out of 5 average rating, 49 reviewsStandalone Cottage surrounded by woods
3–10 Jul
Guest suite in Stamford
4.97 out of 5 average rating, 35 reviewsRetreat in North Stamford
28 Jul – 4 Aug
Cottage in Pound Ridge
4.8 out of 5 average rating, 50 reviewsPrivate Cottage in Pound Ridge
31 Dec – 7 Jan
Guest house in Bedford
5.0 out of 5 average rating, 13 reviewsRed Coat Cottage
17–24 Nov
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