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Vacation Homes in Town of Lewisboro

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Top Cities in Town of Lewisboro

Vacation HomesVacation Homes

Cross River

Cross River

Featured Vacation Homes in Town of Lewisboro

Business or Weekend escape
Pool

Business or Weekend escape

9.2 out of 10, Wonderful, (43)
"Very nice owner with great communication. "
The price is HK$667
HK$1,150 total
includes taxes & fees
10 Aug - 11 Aug
Business or Weekend escape
Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (18)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is HK$1,300
HK$2,468 total
includes taxes & fees
6 Aug - 7 Aug
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Historic Connecticut Home w/ Grill & Spacious Yard
Dining

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (12)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Microwave, oven, stovetop, dishwasher

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Modern NY Home w/ Views By Hudson Valley Hiking!
TV, fireplace, books, video library

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Charming 2-bedroom house with WiFi, AC in Fairfield
Interior

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is HK$1,166
HK$2,730 total
includes taxes & fees
6 Aug - 7 Aug
Charming 2-bedroom house with WiFi, AC in Fairfield
Charming Highland Falls Home < 2 Mi to West Point!
Exterior

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is HK$2,771
HK$5,449 total
includes taxes & fees
3 Sept - 4 Sept
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Beach

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Spacious 4-bedroom house in charming Rye with AC
Miscellaneous

Spacious 4-bedroom house in charming Rye with AC

The price is HK$1,570
HK$3,564 total
includes taxes & fees
5 Aug - 6 Aug
Spacious 4-bedroom house in charming Rye with AC
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Property grounds

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Hickory on Willow Lake
Children’s area

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is HK$3,336
HK$4,818 total
includes taxes & fees
5 Aug - 6 Aug
Hickory on Willow Lake
St Julian's Place - Large updated Apt @ 40 Min NYC
Property grounds

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"This is the 3rd time we've stayed here. The apartment looks great and is convenient for us to visit family. We always enjoy staying here."
St Julian's Place - Large updated Apt @ 40 Min NYC
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.
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Top Town of Lewisboro Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Room was spotless, bed was comfortable, front desk was super friendly. The cleaners were super nice every morning. The pool/hot tub was a nice touch. Highly recommend to anyone looking to stay in the area. "
Joshua 2-night trip
Posted 7 hours ago
Hyatt Regency Greenwich