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 favorite
Home in Wilton
4.96 out of 5 average rating, 139 reviews

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Top guest favorite
An outdoor stone patio features a wooden dining table shaded by a large blue umbrella. Surrounding the table are woven chairs, while a hammock is positioned nearby among the trees. Colorful cushions adorn white armchairs, contributing to a relaxed atmosphere.
Home in Pound Ridge
5 out of 5 average rating, 45 reviews

Private farm cottage +hiking

Private home with large stone patio with access to over 4,000 acres of trails in Ward Pound Ridge. Owner lives on the property and is happy to introduce you to the horses Lincoln, Domino, and Forceti. The house has its own driveway and sits on two acres and is quiet and private. We have a great internet connection, with two working spaces set up in the house (1 in the bedroom and another in the kitchen) for remote work. Enjoy the scenery and tranquility of northern Westchester.

Guest favorite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc
4.98 out of 5 average rating, 119 reviews

French Guest House in Waccabuc

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

Top guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 103 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Apartment in Brookfield
4.92 out of 5 average rating, 293 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.

Superhost
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.8 out of 5 average rating, 238 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.

Top guest favorite
A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.
Cottage in South Salem
4.96 out of 5 average rating, 255 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 favorite
The lakefront view showcases a modern lakehouse surrounded by trees, with large glass windows reflecting the natural surroundings. A stone path leads to the water's edge, where a wooden dock is visible alongside a small green boat.
Home in South Salem
5 out of 5 average rating, 34 reviews

Oscaleta Lake House: Modern Lux

Escapology-A spectacular destination, designed as a luxury Lakehouse with its own dock and 120' private lakefront. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork and furniture throughout this historic 1940's gem. Purpose built for your outdoor routine, Canoeing, Swimming, Hiking, Grilling etc We recommend 3+ nights if you can.

Top guest favorite
The exterior of a charming guesthouse is illuminated during twilight, with warm string lights hanging above a patio area. Large windows reveal the inviting interior, while tall trees frame the scene, creating a serene atmosphere in the evening.
Home in Pound Ridge
5 out of 5 average rating, 173 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.

Top guest favorite
The cottage is nestled among lush greenery, with a sloping yard leading to a rock bed. Large trees partially shade the structure, which features a combination of dark shingles and white trim. Windows allow soft light to illuminate the interior, enhancing the tranquil surroundings.
Cottage in Danbury
4.98 out of 5 average rating, 162 reviews

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

Guest favorite
The studio apartment features a spacious bed with a soft, textured blanket. A round mirror and two bedside lamps are positioned next to the bed. The kitchenette and dining area can be seen in the background, with modern appliances and cabinetry complementing the decor.
Apartment in Danbury
4.95 out of 5 average rating, 109 reviews

Stylish Studio with Kitchen, Central Danbury

‣ Fully Furnished Studio Apartment with kitchenette - Cooktop but no oven ‣ Central Location ‣ Walking distance to Starbuck, C-town, Ridgewood Country Club ‣ Close to the highway (some guests say you can hear cars passing by on the highway) ‣ 2 minutes from Interstate 84 ‣ 15 minutes to Danbury Fair Mall ‣ .5 miles or a 5 to 10 mins walk to food shopping

Guest favorite
A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.
Guesthouse in South Salem
4.93 out of 5 average rating, 314 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) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Popular amenities for Lewisboro vacation rentals

When is the best time to visit Lewisboro?

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Avg. priceG$62,729 GYDG$67,120 GYDG$70,256 GYDG$65,447 GYDG$67,956 GYDG$74,857 GYDG$75,066 GYDG$78,620 GYDG$67,956 GYDG$62,729 GYDG$62,729 GYDG$61,683 GYD
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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 70 house 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 free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Lewisboro have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Lewisboro. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Lewisboro?

    Make yourself at home in Lewisboro by choosing from our most frequently booked neighborhoods. We have over 190 vacation rentals in Ridgefield, over 50 vacation rentals in Bedford Hills, and over 20 vacation rentals in Katonah.

  • 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.

Quick stats about vacation rentals in Lewisboro

  • Total vacation rentals

    Explore 140 vacation rentals in Lewisboro

  • Nightly prices starting at

    Lewisboro vacation rentals start at G$12,546 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Lewisboro vacation rentals include wi-fi 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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