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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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Top guest favorite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

NathanRating, 5 stars4 months ago

This place was a breath of fresh air. I've noticed a trend on AirBNB of rentals that are obviously flipped investment properties with no character and no evidence of life: this place is the opposite! Charming, comfortable, with hosts who actually know the area and live in the area. This is a great family option when visiting the surrounding Hudson Valley towns. I hope I can get back here soon!

Cabin in Boiceville

4.96 out of 5 average rating, 156 reviews

Catskills Cabin Surrounded by Mountain Views+Spa!

LyleRating, 5 stars4 weeks ago

Loved the beautiful mountain views through the large windows or while enjoying the full sized deck. Three large bedrooms were great accommodations for our three couples. Very clean, very roomy and homey feel with lots of attention to the details that make for a smooth stay, Great kitchen facilities - meals were easy. Lots of “hanging out “ space perfect for spending relaxing time together. Loved playing the old vinyl records and board games. Key cabin location enables rapid access to so many activities and sites to see. So happy we chose the Fratt Lodge. We cant wait to come back!

Home in Kerhonkson

4.95 out of 5 average rating, 355 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

EppiRating, 5 stars3 days ago

FENCED. YARD!! Apart from the clean, spacious, well appointed home, the yard was the best part. And it wasn’t just boring and flat and grassy-think boulders for climbing and jumping, hills for racing, “secret passageways” for exploring. Just be prepared to look for ticks. Clearly an excellent choice for families with children, and our dog loved it most. The home has lots of character, good books to read, games for passing time. While venturing out for hikes, we enjoyed the views along the windy roads with charming homes and mountain scenery. The kitchen had so many pots and pans and plenty of dishes. Lillian was always responsive and quick. Good choice for a peaceful getaway.

Top guest favorite

Apartment in Long Beach

4.99 out of 5 average rating, 174 reviews

Incredible Long Beach Private Rental

AllanRating, 5 stars4 months ago

Absolutely superb hosts and such a great location. Steven couldn’t have been a better host, our kids and us loved his place and would highly recommend. Thoughtful touches everywhere and very clean. Hope we can stay again sometime.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

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

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

Apartment in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

Top guest favorite

Home in Millerton

4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago

We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

Home in Litchfield County

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

JadeRating, 5 stars2 months ago

We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!

Condo in Vernon Township

4.96 out of 5 average rating, 74 reviews

Peaceful Mountain Retreat

JulieRating, 5 stars1 week ago

Great condo for a family of five. Plenty of space and everything was clean and inviting. our kids especially loved the loft stocked with games and toys.

Condo in Vernon Township

4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago

We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!

Home in Cornwall

4.82 out of 5 average rating, 95 reviews

State Forest Getaway

GideonRating, 5 stars1 week ago

Elena's house turned out to be a great vacation spot for us. It was conveniently located, very well maintained and guest friendly. Though rustic on the outside, the interior was completely redone, offering all modern amenities you might want. Kitchen was better equipped than most Airbnb's we've stayed at and was fun for us to cook in Without getting into much detail I'll just say that should we be in the area again we'll definitely return to this Airbnb and always recommend it to others

Cottage in Greenwood Lake

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars1 week ago

We had a great time at Carmine's place, highly recommend.

Top guest favorite

Condo in Vernon Township

4.96 out of 5 average rating, 107 reviews

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

GregRating, 5 stars1 month ago

Massimo was so communicative, place was great, and the little extras provided -- snacks, beverages, and the set up for old time arcade games -- totally awesome! Thanks!

Quick stats about vacation rentals in Lewisboro

Total rentals
140 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 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 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 50 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 House Rentals in Lewisboro?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with free parking, over 80 homes with wifi, over 70 homes with air conditioning, over 70 homes with a kitchen, 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.
Do apartment rentals in Lewisboro have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Lewisboro. Enjoy a tailored experience with all the comforts you desire.
Are there Lewisboro house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals 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 apartment rentals in Lewisboro?
Experience the best of Lewisboro with our apartment rentals, starting at about $90 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