Vacation rentals in Lewisboro

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Top-rated vacation rentals in Lewisboro

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Rental unit in Pound Ridge

The Suite at Pound Ridge

Enjoy the beauty Pound Ridge and the surrounding area have to offer from the comfort of your large private suite. The land surrounding the home is state-owned, allowing for a canopy of trees everywhere you look. Check out Leon Levy preserve known for hiking trails right down the road or other preserves right near by. Hungry? The Pound Ridge Inn restaurant is a must and is only a few minutes away. Be sure to also check out the local town shops and take a quick trip over the border to CT. Enjoy!

$199 per night

Guesthouse in Waccabuc

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated 8 acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s like staying in a 5-Star European luxury hotel suite (house designed by David Easton) with heated stone floors and heated towel rack, new top of the line Sealy mattress, gold taps, private entrance and it’s very serene. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train station).

$248 per night

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Guest suite in Bedford

Sweet Suite in walkable historic Bedford Village

Bright and cozy 2 BR apartment with a vintage vibe. High speed Internet/Wifi/Smart TV. Walk right into historic Bedford Village for shops, restaurants, the Bedford Playhouse, churches, groceries, galleries, the public library and the Village Green.

$148 per night