A calm lake reflecting a forested hill during sunset.

Holiday Rentals in Town of Lewisboro

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Our top choices for Town of Lewisboro holiday rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is €234
includes taxes & fees
7 Oct - 8 Oct
DUNE Fairfield Beach
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

2. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is €357
includes taxes & fees
1 Oct - 2 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern living room with a large window, a sofa, a coffee table, and a TV.

3. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (13 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is €175
includes taxes & fees
20 Oct - 21 Oct
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

4. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (185 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is €143
includes taxes & fees
1 Oct - 2 Oct
Stamford Suites
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

5. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is €342
includes taxes & fees
1 Oct - 2 Oct
Luxury Designer 2 bedroom+office/3bed vacation home.
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

6. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is €280
includes taxes & fees
1 Oct - 2 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern living room with a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

7. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is €230
includes taxes & fees
1 Oct - 2 Oct
Spacious Studio with Pool Table
A house surrounded by a dense forest with a hammock and a small shed.

8. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
A campfire with a wooden table and benches by a lake.

9. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is €273
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A house with a view of a bridge and mountains.

10. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is €301
includes taxes & fees
6 Oct - 7 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

11. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is €293
includes taxes & fees
7 Oct - 8 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is €249
includes taxes & fees
12 Oct - 13 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern living room with a sofa, a coffee table, and a bar stool.

13. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is €279
includes taxes & fees
4 Oct - 5 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

14. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is €363
includes taxes & fees
4 Oct - 5 Oct
Guesthouse at Norwalk Inn
Living area

15. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is €224
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-bedroom retreat minutes from West Point!
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

16. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
The price is €274
includes taxes & fees
4 Oct - 5 Oct
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

17. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
The price is €137
includes taxes & fees
6 Oct - 7 Oct
1 King Bed | Non-Smoking
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

18. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is €211
includes taxes & fees
18 Oct - 19 Oct
The Perch in the Purchase -- Cozy, unique, and private
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

19. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is €415
includes taxes & fees
6 Oct - 7 Oct
Local Artist Inspired | Walk to WestPoint + King Bed
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

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

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is €311
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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

Sonesta White Plains Downtown

Sonesta White Plains Downtown

8/10 Good
"Clean room, comfortable bed"
Anthony 1-night trip
Posted 2 hours ago
Sonesta White Plains Downtown

Find out more about Town of Lewisboro

Holiday Homes in Town of Lewisboro

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