Town of Lewisboro Rentals
From $305 per night (USD)VRBO
The Suite at Pound Ridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the beauty Pound Ridge and the surrounding area have to offer from the comfort of your large private suite. The la ...
From $305 per night (USD)VRBO
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Westchester Escape - Estate in Waccabuc 60 Min from NYC
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Thinking of escaping fast paced NYC life for the spring/summer? Look no further. Beautiful Westchester estate on 3 acres ...
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From $3614 per night (USD)VRBO
Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 12
This one of a kind home sits on 10 acres of enclosed compound consisting of the main house (5 bedrooms & 4.5 baths), a 1 ...
From $3614 per night (USD)VRBO
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Dreamy lake house by the beach only 1h from NYC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to our home. Steps to Truesdale lake beach and 1h drive to NYC, you will love summertime here. Enjoy our kayak, ...
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From $758 per night (USD)VRBO
Mid-Century Modern Hilltop Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Spacious modern country retreat sited privately on a hill surrounded by trees with plenty of light. This one of a kind 3 ...
From $758 per night (USD)VRBO
From $845 per night (USD)Expedia
Peaceful Light-Filled Guesthouse 1 Hour From NYC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, ...
From $845 per night (USD)Expedia
From $1317 per night (USD)VRBO
Over Sized Colonial on Private Road.
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
8900sqft. 5 bedrooms, 7 baths, 4 fireplaces, large screened in porch, large hot tub, huge stone patio, stone walls, lots ...
From $1317 per night (USD)VRBO
From $709 per night (USD)VRBO
Your Own House on a Lake
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Perfect house on the lake! Wake up to serene lake views! Kayak from your own private dock and sun deck. Host a diner on ...
From $709 per night (USD)VRBO
From $229 per night (USD)VRBO
Cozy country cottage in horse country ,private 1 hour toNYC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Quiet Country cottage located near New Canaan,Ridgefield,Wilton, Pound Ridge , Bedford. Organic coffee,tea,fruit and sna ...
From $229 per night (USD)VRBO
From $3413 per night (USD)Expedia
Lakefront Estate in Westchester
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Spectacular estate nestled on over 10 private acres with over 300 feet of direct waterfront on Lake Waccabuc, only 1 hou ...
From $3413 per night (USD)Expedia
From $808 per night (USD)VRBO
beautiful contemporary house , only one hour from Manhattan
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Seclusion and serenity in the quaint small town of Pound Ridge only an hour's drive from NYC. Beautiful and renovated co ...
From $808 per night (USD)VRBO
From $381 per night (USD)Expedia
Historic Hideaway with Lake Access!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape from the busy day-to-day at this charming historic hideaway by the lake. The home, circa 1760s, boasts all the st ...
From $381 per night (USD)Expedia
From $404 per night (USD)VRBO
4 Seasons By The Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Adorable, three bedroom three bath cottage with all the luxurious amenities you could possibly want! Master bathroom wit ...
From $404 per night (USD)VRBO
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Newly renovated guesthouse with a patio\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take it easy at this unique and tranquil getaway. Our property is located a 5-min walk from Truesdale lake with access t ...
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Renovated Barn with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
About this space Enjoy summer days by the pool or winters snuggled up by the fire. Unique home with 4+ bedrooms. Situate ...
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From $1463 per night (USD)Expedia
RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
WELCOME TO MOUNTAIN VISTA LUXURY RETREAT. Welcome to the Mountain Vista Luxury Retreat. An architectural marvel nestled ...
From $1463 per night (USD)Expedia
From $262 per night (USD)VRBO
South Salem Vacation Rental w/ Furnished Deck!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover a hidden gem in South Salem, NY, at this charming 1-bed (with a loft), 1-bath vacation rental. Nestled in a ser ...
From $262 per night (USD)VRBO
From $729 per night (USD)VRBO
Fully renovated 4 bedroom lake front home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Freshly renovated house on Lake Waccabuc. Fully furnished with amenities, including bi-monthly house keeping, 2 assigned ...
From $729 per night (USD)VRBO
From $484 per night (USD)VRBO
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This historical 2-bedroom cottage sits next door to the main house, with a separate driveway and entrance, and four park ...
From $484 per night (USD)VRBO
From $2822 per night (USD)VRBO
Luxurious 7-Bedroom Katonah Estate with Pool & Scenic Lake Views.
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Ever dreamed of staying in a French-Italian mansion and feeling like royalty—without leaving New York? Welcome to Luxara ...
From $2822 per night (USD)VRBO
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Beautiful Pound Ridge with a pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perched among the trees of peaceful Pound Ridge, this 4-bedroom retreat feels like your own private treehouse. The spraw ...
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From $1618 per night (USD)VRBO
Outdoor Entertainment Areas: Spacious Katonah Gem!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Home Gym | Fireside Relaxation | Expansive Yard w/ Pool | Near Hiking & Biking Trails Your ultimate getaway with loved ...
From $1618 per night (USD)VRBO
From $183 per night (USD)VRBO
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this delightful gem in Waccabuc. This cozy apartment features 2 queen beds, a living room with a sofa bed, and ...
From $183 per night (USD)VRBO