Compare Town of Lewisboro Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Town of Lewisboro

Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.

Pool

Hot Tub

At this villa, guests have access to features like laundry facilities.

Washer

Dryer

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

$1,444 nightly

$1,565 total

Oct 26 - Oct 27

Total with taxes and fees

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities. This smoke-free villa also has barbecue grills.

Pool

Kitchen

Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.

Kitchen

Washer

Family Retreat with Autumn Views and Game Room

Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.

Pool

Hot Tub

$800 nightly

$905 total

Oct 18 - Oct 19

Total with taxes and fees

This vacation home features a hot tub, laundry facilities, and local meal delivery service. Friendly staff can provide concierge services, and also offer advice about sightseeing. Additional amenities include barbecue grills and a garden.

Hot Tub

Kitchen

Guests staying at this villa enjoy access to a marina, an outdoor pool, and free WiFi in public areas. You can take advantage of free parking if you drive. This smoke-free villa also has a garden.

Pool

Kitchen

Scenic Spring Home With Outdoor Dining Charm

Guests staying at Family Retreat With Autumn Views and Fireplace enjoy a gym, WiFi in public areas, and a garden. Free parking is included with your stay.

Pet friendly

Parking included

Charming 2-bedroom villa in serene Holmes with AC, WiFi

This villa is a smoke-free villa.

Pool

Air conditioning

Don't see what you're looking for?

See all available properties in Town of Lewisboro

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Villas

Book luxury villas in Town of Lewisboro
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Town of Lewisboro. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Town of Lewisboro, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Town of Lewisboro
You won’t have a problem finding your own space in Town of Lewisboro. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Town of Lewisboro on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Town of Lewisboro rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Town of Lewisboro Villas essential information

Accommodation	11 Villas
Lowest Price	$905
Highest Price	$1,565
Popular accommodation	Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Spacious Retreat w/ Pool, Hot Tub & Game Room, Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT, 3 bedroom villa in bridgeport, Family Retreat with Autumn Views and Game Room, 7BD house home party wedding , Hudson Valley Estate on 4 Acres w/ Private Pool!, Scenic Spring Home With Outdoor Dining Charm, Charming 2-bedroom villa in serene Holmes with AC, WiFi