Vacation rentals in Lewisboro

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Top-rated vacation rentals in Lewisboro

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

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Top guest favourite
A serene yoga studio features a black yoga mat complemented by a wooden block. Large sliding glass doors provide a view of the lush forest outside, enhancing the natural tranquility of the space.
Cottage in Warwick
4.99 out of 5 average rating, 124 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top guest favourite
Guest suite in Wilton
4.91 out of 5 average rating, 176 reviews

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Guest favourite
A tranquil scene of the property showcases a green lawn with lush trees and a fire pit, surrounded by natural landscapes. The classic colonial home stands in the background, offering a serene view of the outdoor space.
Guest suite in South Salem
4.93 out of 5 average rating, 332 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds, 1 sofa bed ) totally self contained apt over 2 floors ,with its own seperate entrance.The ground floor has a mud room and full eat in kitchen.The 1 st floor has a sitting room,bathroom and 2 bedrooms. The space is the end wing of and attached to Shaker Hollow, a classic 1795 colonial.A Stone patio with outdoor furniture overlooks 3 1/2 acres of garden and a meadow .There is the use of a large fire pit and gas BBQ.

Top guest favourite
Cottage in South Salem
5 out of 5 average rating, 127 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

Guest favourite
Barn in Katonah
4.96 out of 5 average rating, 138 reviews

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers blooming in June, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool and cedar hot tub. Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Guest favourite
A private, gated entrance is illuminated by soft lights lining the gravel driveway. Lush trees frame the pathway, leading towards a stately home that glows warmly in the evening light. The manicured lawn enhances the serene setting.
Guesthouse in Waccabuc
4.99 out of 5 average rating, 135 reviews

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Top guest favourite
A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.
Home in Pound Ridge
5 out of 5 average rating, 182 reviews

Peaceful Light-Filled Guesthouse salt pool/sauna

**Pool open, as of May 18, 2026.** Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna.. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Guest favourite
Cottage in South Salem
4.96 out of 5 average rating, 267 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Top guest favourite
Cottage in Pawling
4.99 out of 5 average rating, 169 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favourite
A serene outdoor pool is set within a tranquil environment, surrounded by lush greenery. The water appears inviting and clear, with a gentle ripple effect on the surface. A wooden deck borders the pool, creating a spacious area for relaxation.
Guesthouse in Bedford
4.92 out of 5 average rating, 229 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Top guest favourite
A quaint blue cottage is nestled among vibrant trees, reflecting a peaceful aesthetic. The pond in the foreground features natural greenery and a water fountain, creating a serene environment surrounded by nature.
Cottage in Redding
4.94 out of 5 average rating, 287 reviews

Cozy Cottage by the pond

This sweet little cottage on our pond is your perfect mini vacation with direct access to one of CT's best kept secrets, Huntington State Park is steps away. Peaceful and quiet you can also hike, bike, kayak, x/c ski and explore the countryside.

Top guest favourite
Home in Katonah
4.92 out of 5 average rating, 104 reviews

Peace and Stunning Views in Katonah

A fully renovated, immaculate home with endless views, glorious sunsets and privacy - only 10 minutes from downtown Katonah. With a wide open floor plan, and floor to ceiling sunny windows, this is a perfect house for relaxing or entertaining.

Popular amenities for Lewisboro vacation rentals

When is the best time to visit Lewisboro?

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Frequently Asked Questions

  • Are there family-friendly house rentals in Lewisboro?

    Lewisboro has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Lewisboro?

    Experience the best of Lewisboro with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly house rentals in Lewisboro?

    Four-legged friends are welcome in Lewisboro. Choose from more than 20 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Lewisboro?

    Yes! Work meets play with ease at over 50 house rentals in Lewisboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Lewisboro house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Lewisboro, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Lewisboro?

    Make yourself at home in Lewisboro by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Bedford Hills, over 20 vacation rentals in Katonah, and over 180 vacation rentals in Ridgefield.

  • Do guesthouse rentals in Lewisboro have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lewisboro have a kitchen?

    Absolutely! We offer over 70 house rentals with a kitchen in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Lewisboro have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lewisboro have free parking?

    Absolutely! We offer over 70 house rentals with free parking in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Lewisboro

  • Total vacation rentals

    Explore 130 vacation rentals in Lewisboro

  • Nightly prices starting at

    Lewisboro vacation rentals start at $83 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Lewisboro vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lewisboro rentals

  • 4.9 Average rating

    Lewisboro stays are highly rated by guests—averaging 4.9 out of 5!

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