Town of Lewisboro, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Lewisboro, New York on RentalSaver.com!

Town of Lewisboro Rentals

From $249 per night (USD)
VRBO
The Suite at Pound Ridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the beauty Pound Ridge and the surrounding area have to offer from the comfort of your large private suite. The la ...
From $249 per night (USD)
VRBO
$Lakefront\/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem$
From $975 per night (USD)
Expedia
Lakefront\/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem
Bedrooms:
4
Bathrooms:
3
Sleeps:
9
Newly renovated modern lakefront house (3 full bathrooms and 3 bedrooms), in a charming and relaxing neighborhood, with ...
From $975 per night (USD)
Expedia
Click For Pricing
VRBO
Dreamy lake house by the beach only 1h from NYC
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to our home. Steps to Truesdale lake beach and 1h drive to NYC, you will love summertime here. Enjoy our kayak, ...
Click For Pricing
VRBO
$South Salem Vacation Rental w\/ Furnished Deck!$
From $239 per night (USD)
Expedia
South Salem Vacation Rental w\/ Furnished Deck!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover a hidden gem in South Salem, NY, at this charming 1-bed (with a loft), 1-bath vacation rental. Nestled in a ser ...
From $239 per night (USD)
Expedia
From $463 per night (USD)
VRBO
Mid-Century Modern Hilltop Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Spacious modern country retreat sited privately on a hill surrounded by trees with plenty of light. This one of a kind 3 ...
From $463 per night (USD)
VRBO
From $2310 per night (USD)
VRBO
Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!
Bedrooms:
7
Bathrooms:
8
Sleeps:
12
This one of a kind home sits on 10 acres of enclosed compound consisting of the main house (5 bedrooms & 4.5 baths), a 1 ...
From $2310 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Cozy country cottage in horse country ,private 1 hour toNYC
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Quiet Country cottage located near New Canaan,Ridgefield,Wilton, Pound Ridge , Bedford. Organic coffee,tea,fruit and sna ...
From $225 per night (USD)
VRBO
Click For Pricing
VRBO
Modern Hudson Valley Farmhouse just 50 min from NYC
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
A completely renovated 1847 Victorian Farmhouse on a private 10 acre farm. This antique farmhouse features all the moder ...
Click For Pricing
VRBO
From $399 per night (USD)
VRBO
Historic Hideaway with Lake Access!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Escape from the busy day-to-day at this charming historic hideaway by the lake. The home, circa 1760s, boasts all the st ...
From $399 per night (USD)
VRBO
From $638 per night (USD)
VRBO
Your Own House on a Lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Perfect house on the lake! Wake up to serene lake views! Kayak from your own private dock and sun deck. Host a diner on ...
From $638 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Serenity Awaits at this Cozy Lakeside Bungalow
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Twin Lakes Cottage is a dreamy lakeside getaway in South Salem, NY in Westchester County, less than 90 minutes from ...
From $420 per night (USD)
VRBO
Click For Pricing
Expedia
Westchester Escape - Estate in Waccabuc 60 Min from NYC
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
Thinking of escaping fast paced NYC life for the spring/summer? Look no further. Beautiful Westchester estate on 3 acres ...
Click For Pricing
Expedia
From $550 per night (USD)
VRBO
LIVE ON A BEAUTIFUL LAKE one hour from New York City!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy dinner with a view of Lake Waccabuc, a glacial lake one hour north of New York City. It is connected by canal to ...
From $550 per night (USD)
VRBO
$Newly renovated guesthouse with a patio\n$
From $200 per night (USD)
VRBO
Newly renovated guesthouse with a patio\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Take it easy at this unique and tranquil getaway. Our property is located a 5-min walk from Truesdale lake with access t ...
From $200 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
Large lakehouse, fishing, kayaking, heated pool, fireplaces multiple bedrooms!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Situated on a private lake with direct access to Lake Whatmore, our property has sprawling views of the water where you ...
From $1000 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Spacious Lake Home for Peace and Relaxation
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Unwind at our lakefront retreat, just an hour from NYC. The perfect blend of relaxation and recreation. During warmer mo ...
From $639 per night (USD)
Expedia
From $350 per night (USD)
VRBO
4 Seasons By The Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Adorable, three bedroom three bath cottage with all the luxurious amenities you could possibly want! Master bathroom wit ...
From $350 per night (USD)
VRBO
From $3000 per night (USD)
Expedia
Lakefront Estate in Westchester
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Spectacular estate nestled on over 10 private acres with over 300 feet of direct waterfront on Lake Waccabuc, only 1 hou ...
From $3000 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Lake Front Cozy Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Get back to nature. Hiking trails 1 mile away. Lake view and sunsets to die for. Kayaks available ( in season) Relax and ...
From $325 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Bucolic Pound Ridge with Pool- long term available
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful Bucolic Pound Ridge. Short drive to North Salem horse country, Mount Kisco shopping, Ridgefield Ct, Playhouse ...
From $311 per night (USD)
Expedia
From $764 per night (USD)
VRBO
Over Sized Colonial on Private Road.
Bedrooms:
8
Bathrooms:
5
Sleeps:
16
8900sqft. 5 bedrooms, 7 baths, 4 fireplaces, large screened in porch, large hot tub, huge stone patio, stone walls, lots ...
From $764 per night (USD)
VRBO
From $625 per night (USD)
Expedia
Peaceful Light-Filled Guesthouse 1 Hour From NYC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enter a freshly updated and thoughtfully furnished peaceful home surrounded by 14 acres of ancient trees, stone walls, a ...
From $625 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Charming Cottage located on Historic Estate 1 Hour from NYC!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
If you are looking to experience the true essence of southern New England this is the place! Impeccably restored in the ...
From $338 per night (USD)
VRBO
Click For Pricing
VRBO
Renovated Barn with Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
About this space Enjoy summer days by the pool or winters snuggled up by the fire. Unique home with 4+ bedrooms. Situate ...
Click For Pricing
VRBO
From $700 per night (USD)
VRBO
beautiful contemporary house only 1 hour from Manhattan
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Seclusion and serenity only an hour's drive from NYC. Beautiful contemporary home sitting on 6.2 gorgeous acres of lush ...
From $700 per night (USD)
VRBO
Click For Pricing
Expedia
Restored 1860 Historic Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Tinker Toy Farm! Recently renovated, this 1860 modern farmhouse is bursting with charm. Overlooking the Cross ...
Click For Pricing
Expedia
$Contemporary Pet-Friendly Retreat w\/ Game Room, Fireplace & HBOMax$
From $399 per night (USD)
VRBO
Contemporary Pet-Friendly Retreat w\/ Game Room, Fireplace & HBOMax
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Just an hour from Manhattan by train or car, come retreat to your own 3bedroom, 2.5 bath home with private pool. With it ...
From $399 per night (USD)
VRBO
From $1280 per night (USD)
VRBO
NEW OUTDOOR SPA ROOM WITH HOT TUB, FAST WI-FI, SMART TV AND A BREATHTAKING VIEW.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
WELCOME TO MOUNTAIN VISTA LUXURY RETREAT. Welcome to the Mountain Vista Luxury Retreat. An architectural marvel nestled ...
From $1280 per night (USD)
VRBO
From $750 per night (USD)
VRBO
Cozy Historic Estate on 3 acres with Chef's Kitchen, Fireplaces, Pool, Hot Tub
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Step back in time while you relax with the whole family at this peaceful Revolutionary War-era estate in the Connecticut ...
From $750 per night (USD)
VRBO
Click For Pricing
VRBO
Relaxing summer retreat across from 4,000-acre reservation
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our charming house is one half 1940s woodworker’s dream, one half bright and contemporary open space with high ceilings. ...
Click For Pricing
VRBO

RentalSaver.com Compare. Rent. Save

Search Your Destination Now!

Town of Lewisboro Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 30 Rentals

The Suite at Pound Ridge

Lakefront\/nature retreat, 50 miles from NYC, close to Le Chateau (South Salem

Dreamy lake house by the beach only 1h from NYC

South Salem Vacation Rental w\/ Furnished Deck!

Mid-Century Modern Hilltop Retreat

Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!

Cozy country cottage in horse country ,private 1 hour toNYC

Modern Hudson Valley Farmhouse just 50 min from NYC

Historic Hideaway with Lake Access!

Your Own House on a Lake

Serenity Awaits at this Cozy Lakeside Bungalow

Westchester Escape - Estate in Waccabuc 60 Min from NYC

LIVE ON A BEAUTIFUL LAKE one hour from New York City!

Newly renovated guesthouse with a patio\n

Large lakehouse, fishing, kayaking, heated pool, fireplaces multiple bedrooms!

Spacious Lake Home for Peace and Relaxation

4 Seasons By The Lake

Lakefront Estate in Westchester

Lake Front Cozy Cottage

Bucolic Pound Ridge with Pool- long term available

Over Sized Colonial on Private Road.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Charming Cottage located on Historic Estate 1 Hour from NYC!

Renovated Barn with Pool!

beautiful contemporary house only 1 hour from Manhattan

Restored 1860 Historic Home

Contemporary Pet-Friendly Retreat w\/ Game Room, Fireplace & HBOMax

NEW OUTDOOR SPA ROOM WITH HOT TUB, FAST WI-FI, SMART TV AND A BREATHTAKING VIEW.

Cozy Historic Estate on 3 acres with Chef's Kitchen, Fireplaces, Pool, Hot Tub

Relaxing summer retreat across from 4,000-acre reservation