A calm lake reflecting a forested hill during sunset.

Vacation Rentals in Town of Lewisboro

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Our top choices for Town of Lewisboro vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (191 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥21,107
￥24,273 total
includes taxes & fees
Oct 12 - Oct 13
Stamford Suites
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥28,089
￥41,959 total
includes taxes & fees
Oct 12 - Oct 13
DUNE Fairfield Beach
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

3. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is ￥15,831
￥29,338 total
includes taxes & fees
Oct 12 - Oct 13
Welcome to Sweet Abby Rose!
A modern living room with a large window, a sofa, a coffee table, and a TV.

4. 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, (14 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is ￥17,572
￥30,815 total
includes taxes & fees
Nov 9 - Nov 10
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,206
￥47,995 total
includes taxes & fees
Oct 13 - Oct 14
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

6. 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 ￥50,013
￥57,515 total
includes taxes & fees
Oct 20 - Oct 21
Guesthouse at Norwalk Inn
A swimming pool at night with blue lighting.

7. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is ￥14,248
￥24,103 total
includes taxes & fees
Oct 18 - Oct 19
Business or Weekend escape
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

8. 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 ￥23,430
￥68,718 total
includes taxes & fees
Oct 12 - Oct 13
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 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 ￥19,615
￥36,391 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom retreat minutes from West Point!
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.

10. 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 ￥16,670
￥50,596 total
includes taxes & fees
Oct 18 - Oct 19
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Private kitchen

11. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is ￥23,747
￥42,507 total
includes taxes & fees
Oct 12 - Oct 13
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern living room with a sofa, a coffee table, and a bar stool.

12. 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 ￥22,797
￥49,646 total
includes taxes & fees
Oct 18 - Oct 19
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

13. 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 ￥23,082
￥36,874 total
includes taxes & fees
Oct 25 - Oct 26
The Perch in the Purchase -- Cozy, unique, and private
A motel with a blue awning and a '6 Now Open' sign.

14. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
9.0 out of 10, Wonderful, (4 reviews)
"Short trip so just needed something quick, location near Westchester Airport suited us well."
United States
Anonymous traveler
The price is ￥18,372
￥21,014 total
includes taxes & fees
Oct 12 - Oct 13
1 Queen Bed | Non-Smoking
A campfire with a wooden table and benches by a lake.

15. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥27,071
￥55,195 total
includes taxes & fees
Oct 12 - Oct 13
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

16. 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 ￥26,754
￥44,235 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

17. 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
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥24,934
￥51,472 total
includes taxes & fees
Oct 13 - Oct 14
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

18. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
The price is ￥19,757
￥49,950 total
includes taxes & fees
Nov 2 - Nov 3
Renovated 2BR Retreat / Modern Comforts Included
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

19. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.8 out of 10, Good, (6 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is ￥23,935
￥55,982 total
includes taxes & fees
Oct 18 - Oct 19
Modern 2 Bed in BlackRock
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.

20. '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 ￥24,506
￥48,851 total
includes taxes & fees
Nov 1 - Nov 2
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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

West Gate Inn Nyack

West Gate Inn Nyack

8/10 Good
"The price was cheap. The rooms are old and need updated. Things were clean. Breakfast is free for as long as you stay."
Laura 4-night trip
Posted less than an hour ago
West Gate Inn Nyack

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Vacation Apartments in Town of Lewisboro

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