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

Apartment in Mount Kisco

4.93 out of 5 average rating, 149 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.

Oct 31 – Nov 7

G$27,718 GYD per night

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

Jan 1 – 8

G$34,869 GYD per night

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…

Aug 5 – 12

G$29,178 GYD per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 208 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.

Aug 23 – 30

G$24,325 GYD per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 3 – 10

G$26,116 GYD per night

Guest favorite

Cottage in South Salem

4.96 out of 5 average rating, 113 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.

Oct 5 – 12

G$72,427 GYD per night

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.

Oct 18 – 25

G$29,803 GYD per night

Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 539 reviews

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

Mar 22 – 29

G$32,371 GYD per night

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.

Sep 17 – 24

G$25,478 GYD per night

Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 126 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.

Sep 22 – 29

G$145,178 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 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

Nov 26 – Dec 3

G$25,907 GYD per night

Guest favorite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Oct 7 – 14

G$21,266 GYD per night

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

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Feb 18 – 25

G$17,622 GYD per night

Guest favorite

Cottage in South Salem

4.96 out of 5 average rating, 181 reviews

Private cottage in horse country &1 hour from NYC!

Aug 29 – Sep 5

G$51,088 GYD per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 reviews

Peekskill Carriage House Downtown Studio

Oct 28 – Nov 4

G$27,401 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

Sep 27 – Oct 4

G$28,238 GYD per night

Guest favorite

Home in Pound Ridge

5.0 out of 5 average rating, 18 reviews

Private farm cottage +hiking

Aug 27 – Sep 3

G$43,246 GYD per night

Guest favorite

Guesthouse in South Salem

5.0 out of 5 average rating, 66 reviews

Newly renovated guesthouse with a patio

Jul 12 – 19

G$42,356 GYD per night

Guest favorite

Cottage in Bedford

5.0 out of 5 average rating, 57 reviews

Clover Cottage

Mar 3 – 10

G$40,846 GYD per night

Guest favorite

Guest suite in Wilton

4.95 out of 5 average rating, 39 reviews

Guest suite with private enter

Jul 28 – Aug 4

G$20,342 GYD per night

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
G$12,509 GYD 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 wifi, over 10 homes with free parking, over 10 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 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.

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

Guest suite in Haverstraw

Cottage in South Salem

Guesthouse in Peekskill

Cottage in Cortlandt

Home in Pound Ridge

Guesthouse in South Salem

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 Cottage 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 cottage rentals in Lewisboro?

Do house rentals in Lewisboro have a kitchen?

Destinations to explore