Photo by Marina Timo

Holiday Rentals in Town of Lewisboro

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Town of Lewisboro

Interior
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Waccabuc
4.0 out of 10, (2)
"Clean but minimalist, big empty basement, good for a cheap stay near Caramoor"
United States
Patrick M.
The price is €183
includes taxes & fees
14 Nov - 15 Nov
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.
Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (75)
"Great stay"
Canada
Gilles
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
United States
Brian
The price is €277
includes taxes & fees
16 Nov - 17 Nov
Guesthouse at Norwalk Inn
Front of property
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property
Bridgeport
The price is €998
includes taxes & fees
18 Nov - 19 Nov
Beechmont - Perfect for Family Retreat!
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.0 out of 10, (70)
"It was great"
United States
Natalie
The price is €131
includes taxes & fees
16 Nov - 17 Nov
Stamford Suites
2 bedrooms, iron/ironing board, travel cot, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included

West End - West Side
10.0 out of 10, Exceptional, (2)
"My stay was comfortable for an over night stay after family celebration. I would definitely use this unit again if I travel without a senior person. My suggestion is to clearly identify the unit regarding the stair climbing for prospective renters for the second and third floor. Thank you,"
United States
Magalie L.
The price is €255
includes taxes & fees
1 Dec - 2 Dec
Renovated 2BR Retreat / Modern Comforts Included
Fridge, microwave, oven, stovetop
Designer 3BR Treehouse w/ Soaking Tub & Skylights

Designer 3BR Treehouse w/ Soaking Tub & Skylights

Fairfield
10.0 out of 10, Exceptional, (1)
"We came to stay near our son at Sacred Heart. The neighborhood is cute, the house is a perfect size and the location was close to everything we needed."
United States
Sarah M.
The price is €567
includes taxes & fees
30 Nov - 1 Dec
Designer 3BR Treehouse w/ Soaking Tub & Skylights
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
The price is €518
includes taxes & fees
16 Nov - 17 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.
Fridge, microwave, oven, stovetop
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Fairfield
10.0 out of 10, Exceptional, (10)
"This house is adorable! We rented it for our adult children and two grandchildren for our wedding weekend. The owner is excellent at communicating and providing information about things to do in the area. The house is immaculate and the sleeping quarters are perfect! I would definitely recommend this house for a family looking in the area and am keeping their information in my records for future use! Cannot say enough good things about the house and the owner!"
United States
Judy F.
The price is €443
includes taxes & fees
17 Nov - 18 Nov
Bright Escape, Top-Rated Design, Fire pit, Near Beach
Outdoor dining
Updated, cozy single family in Fairfield County

Updated, cozy single family in Fairfield County

Trumbull
9.4 out of 10, Exceptional, (12)
"The house was lovely and exactly as pictured. Our family of 5 had plenty of room and enjoyed the games downstairs and the large backyard. The house is very conveniently located to restaurants, shops and the Merritt Parkway. We have family nearby and would live to stay again!"
United States
Jessica B.
The price is €412
includes taxes & fees
17 Nov - 18 Nov
Updated, cozy single family in Fairfield County
Pool
Business or Weekend escape

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Very nice stay and very clean"
United States
Markel W.
The price is €125
includes taxes & fees
18 Nov - 19 Nov
Business or Weekend escape
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport
9.6 out of 10, Exceptional, (4)
"Extremely clean and well prepared home stocked with items we may need. Plenty of space for all guests. Comfortable beds. Felt safe with the use of electronic keypad entry and security system. Very well maintained. Historic feel with modern amenities. Great location in regards to where we needed to be. Able to communicate with host who assisted in accommodations. Plenty of parking. Lovely place. "
United States
natalie c.
The price is €1,223
includes taxes & fees
14 Nov - 15 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is €168
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom retreat minutes from West Point!
5 bedrooms, desk, iron/ironing board, free WiFi
Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard

West End - West Side
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
Modern + Spacious 5BR/2BA Home, Renovated Backyard
2 bedrooms, iron/ironing board, WiFi, bed sheets
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.

Downtown Bridgeport
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
1 bedroom, desk, iron/ironing board, free WiFi
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
The price is €145
includes taxes & fees
17 Nov - 18 Nov
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Interior
Sweet Studio w/ Lounge & Pool Table

Sweet Studio w/ Lounge & Pool Table

Westport
8.8 out of 10, Excellent, (6)
"This was our first time getting a VRBO while coming up for a family July 4th party. Everything was great. The space was clean and very comfortable and looked just like the pictures. It was only 5 minutes from our family’s house and very easy to find and in a nice neighborhood. The host was great and very easy to communicate with. "
United States
Annamarie W.
Sweet Studio w/ Lounge & Pool Table
Outdoor dining
Candlewood Lake Retreat; Dock, Game Room & Firepit

Candlewood Lake Retreat; Dock, Game Room & Firepit

New Milford
10.0 out of 10, Exceptional, (48)
"Everything was great! Thank you!"
United States
Ari W.
The price is €1,202
includes taxes & fees
16 Nov - 17 Nov
Candlewood Lake Retreat; Dock, Game Room & Firepit
Fridge, microwave, oven, stovetop
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Carmel Hamlet
10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
United States
Maueen Q.
The price is €866
includes taxes & fees
15 Nov - 16 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is €190
includes taxes & fees
16 Nov - 17 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Lewisboro Hotel Reviews

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

10/10 Excellent
"I Don't understand other guests Disappointment. This place was a gem 💎 Great Location, parking was cheap and the breakfast was filling. Public piano provided great entertainment. "
GLYNN 1-night trip
Posted 2 days ago
The Armon Stamford Hotel & Conference

Find out more about Town of Lewisboro

Holiday Homes in Town of Lewisboro

Search for holiday homes in Town of Lewisboro on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Town of Lewisboro using one of the methods below: 

  • View our selection of featured holiday homes in Town of Lewisboro
  • Use the map to find apartments and other holiday rentals in the Town of Lewisboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Town of Lewisboro while they last

Look no further and take a look at our great range of rental properties in Town of Lewisboro!