Vacation rentals in Lewisboro

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Top-rated vacation rentals in Lewisboro

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Guest favorite

Apartment in Mount Kisco

4.93 out of 5 average rating, 148 reviews

Cozy 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.

Guest favorite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

Guest favorite

Guest suite in Wilton

4.9 out of 5 average rating, 103 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 favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 reviews

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.

Guest favorite

Cottage in South Salem

4.96 out of 5 average rating, 112 reviews

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.

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

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.

Guest favorite

Cottage in South Salem

4.96 out of 5 average rating, 180 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 :)

Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 125 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Enter a freshly updated and 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.

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

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:)

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 reviews

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

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lewisboro vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Lewisboro's top sights

Ridgefield Playhouse32 locals recommend

King Kone11 locals recommend

Le Chateau3 locals recommend

Mountain Lakes Park8 locals recommend

Muscoot Tavern10 locals recommend

Prospector Theater15 locals recommend

Other great vacation rentals in Lewisboro

Guest favorite

Cottage in Danbury

4.97 out of 5 average rating, 111 reviews

Fern Grove Cottage

Guest favorite

Cottage in Pound Ridge

4.93 out of 5 average rating, 170 reviews

Adirondacks in Westchester

Guest favorite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 112 reviews

Barrett's Sanctuary

Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 18 reviews

Private farm cottage +hiking

Guest favorite

Guesthouse in South Salem

5.0 out of 5 average rating, 66 reviews

Newly renovated guesthouse with a patio

Guest favorite

Guesthouse in Waccabuc

4.97 out of 5 average rating, 32 reviews

French Guest House in Waccabuc

Guest favorite

Cottage in Bedford

5.0 out of 5 average rating, 57 reviews

Clover Cottage

Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 34 reviews

Guest suite with private enter

Show all

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 House Rentals in Lewisboro?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with air conditioning, over 80 homes with wifi, over 80 homes with free parking, over 70 homes with a kitchen, 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.

Vacation rentals in Lewisboro

Top-rated vacation rentals in Lewisboro

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Lewisboro vacation rentals

Stay near Lewisboro's top sights

Other great vacation rentals in Lewisboro

Cottage in Danbury

Cottage in Pound Ridge

Guesthouse in Bedford Hills

Home in Pound Ridge

Guesthouse in South Salem

Guesthouse in Waccabuc

Cottage in Bedford

Guest suite in Wilton

Quick stats about vacation rentals in Lewisboro

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Lewisboro?

Are there vacation rentals with a dedicated workspace in Lewisboro?

Are there pet-friendly vacation rentals in Lewisboro?

Do house rentals in Lewisboro have air conditioning?

What are the most popular amenities for House Rentals in Lewisboro?

Do cottage rentals in Lewisboro have wifi?

Do cottage rentals in Lewisboro have free parking?

Are there Lewisboro vacation rentals on Airbnb with pools?

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

Do cottage rentals in Lewisboro have a kitchen?

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