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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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Guest suite in Wilton

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…

Guesthouse in Norwalk

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Cottage in South Salem

Serene lake front cottage 1 hour from NYC

Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.

Barn in Mount Kisco

NY Rustic Cottage Getaway

minimum of 3 nights during Covid-19 in order to keep things safe for guests... Prices are slightly elevated winter due to the cost of oil Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Rental unit in Brookfield

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Cottage in South Salem

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 :)

Guest suite in Haverstraw

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Guesthouse in Mahopac

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Enter a thoughtfully furnished peaceful home surrounded by 14 acres of ancient trees, stone walls, and open meadows, in the town of Pound Ridge, NY. This natural light-filled guesthouse features all the elements needed to relax and unwind. In the summer months, guests have access to a heated saltwater pool, bask in the sun under a majestic maple tree, and enjoy the outdoor fire pit while stargazing at night.

Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Cottage in Bedford

Tudor Cottage In Heart of Bedford

Come stay in open fresh air!!!! Discount for lengthy stays!!! Delightful Tudor Cottage set in heart of Bedford, next to BRLA and numerous barns, preserves and great towns for shopping and dining. Recently renovated with two bedrooms, bathroom, full kitchen and washer dryer. The perfect country get away only 45 mins away from NYC!

Vacation rentals for every style

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Lewisboro vacation rentals

Free parking on premises

Air conditioning

Stay near Lewisboro's top sights

Grand Prix New York Racing & Entertainment8 locals recommend

Muscoot Farm33 locals recommend

Grace Farms31 locals recommend

Wolf Conservation Center - BY APPOINTMENT ONLY13 locals recommend

Katonah Museum of Art32 locals recommend

Mountain Lakes Park8 locals recommend

Other great vacation rentals in Lewisboro

Guesthouse in Peekskill

Peekskill Carriage House Downtown Studio

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

Rental unit in Mount Kisco

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

Cottage in Cortlandt

The Little Cottage in the Woods

Guesthouse in Katonah

Adorable one bedroom guesthouse

Rental unit in Stamford

Standalone Cottage surrounded by woods

Guesthouse in Waccabuc

French Guest House in Waccabuc

Home in Pound Ridge

Private farm cottage +hiking

Quick stats about vacation rentals in Lewisboro

Total rentals
130 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
$60 before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Lewisboro?
Lewisboro has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Lewisboro?
Yes! Work meets play with ease at over 80 vacation rentals in Lewisboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Lewisboro?
Four-legged friends are welcome in Lewisboro. Choose from more than 40 vacation rentals for guests traveling with pets.
Do house rentals in Lewisboro have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Lewisboro?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do cottage rentals in Lewisboro have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Lewisboro have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
Are there Lewisboro vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Lewisboro, available on Airbnb. Make a splash and soak up the sun in style!
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.
Do cottage rentals in Lewisboro have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore