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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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Guesthouse in Wilton

4.96 out of 5 average rating, 111 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Guest suite in Wilton

4.9 out of 5 average rating, 132 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…

Guesthouse in Mahopac

4.94 out of 5 average rating, 173 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ other dining/ takeout options + excellent boba tea shop! Drivable to farm fresh food markets, restaurants and art museums. Endless nearby cute towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to the trails of Volz park!

Guesthouse in Bedford Hills

4.88 out of 5 average rating, 128 reviews

Barrett's Sanctuary

Airy, bright guest house with with access to a gunite pool, patio and expansive backyard for practicing your short game, playing disc golf or other sports. Loft (accessible by spiral staircase) furnished with queen bed. Single bed in alcove off living room. Central air/heat. Washer/dryer. Kitchenette w/ dishwasher. Satellite TV. LR w/ stone fireplace. Minutes to train (1h to Manhattan) and highways. Shopping/restaurants nearby. Delivery available from Seamless, Instacart and more.

Cottage in South Salem

4.97 out of 5 average rating, 130 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.

Rental unit in Redding

4.94 out of 5 average rating, 476 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your HOLIDAY getaway to the Huckleberry Quarters, a totally renovated 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 HOLIDAY getaway, writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Guest suite in Wilton

4.85 out of 5 average rating, 125 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Cottage in South Salem

4.95 out of 5 average rating, 221 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 :)

Home in Pound Ridge

5 out of 5 average rating, 148 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

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. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Guesthouse in Brewster

4.99 out of 5 average rating, 312 reviews

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.

Barn in Mount Kisco

4.91 out of 5 average rating, 563 reviews

NY Rustic Cottage Getaway

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

Guesthouse in Bedford

4.92 out of 5 average rating, 193 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.

Vacation rentals for every style

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Unique stays

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Popular amenities for Lewisboro vacation rentals

Free parking on premises

Air conditioning

Stay near Lewisboro's top sights

Ward Pound Ridge Reservation58 locals recommend

The Inn at Pound Ridge47 locals recommend

Ridgefield Playhouse32 locals recommend

Katonah Museum of Art32 locals recommend

Grace Farms31 locals recommend

The Aldrich Contemporary Art Museum29 locals recommend

Other great vacation rentals in Lewisboro

Home in Bedford

5 out of 5 average rating, 25 reviews

The Waterside Home - Pool, Tennis, Sauna & Golf

Rental unit in Bedford

4.96 out of 5 average rating, 26 reviews

Charming Cottage in historic Bedford Village

Home in Bedford

4.93 out of 5 average rating, 57 reviews

Bedford Paradise Getaway | Hot Tub | Town Center

Home in South Salem

4.94 out of 5 average rating, 34 reviews

Historic Hideaway - Lake Access

Home in South Salem

5 out of 5 average rating, 9 reviews

Casa Luna Lake House

Cottage in Pound Ridge

4.81 out of 5 average rating, 58 reviews

Pound Ridge Paradise: Your Private Cottage Retreat

Guesthouse in South Salem

4.78 out of 5 average rating, 9 reviews

Cozy In-Law Suite in South Salem

Rental unit in Mount Kisco

4.9 out of 5 average rating, 73 reviews

Clean,Comfy & Convenient. Private 1Bed Village Apt

Quick stats about vacation rentals in Lewisboro

Total rentals
130 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

Are there family-friendly vacation rentals in Lewisboro?
Lewisboro has more than 70 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 boutique hotel rentals in Lewisboro have air conditioning?
Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Boutique Hotel Rentals in Lewisboro?
Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Lewisboro have wifi?
Absolutely! We offer over 70 house rentals with wifi in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
Do boutique hotel rentals in Lewisboro have free parking?
Absolutely! We offer over 10 boutique hotel 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 cottage rentals in Lewisboro?
Experience the best of Lewisboro with our cottage 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 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.

Destinations to explore