Photo by Marina Timo

Town of Lewisboro Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Top Holiday Rentals Destinations in Town of Lewisboro

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is NZ$814
includes taxes & fees
2 July - 3 July
My little place Cozy Open concept for quiet time.

Business or Weekend escape

9.4 out of 10, Exceptional, (39)
"Very nice owner with great communication. "
The price is NZ$242
includes taxes & fees
6 July - 7 July
Business or Weekend escape

Seaview Ave House-4BR/8PPL Retreat

9.6 out of 10, Exceptional, (10)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
The price is NZ$1,219
includes taxes & fees
2 July - 3 July
Seaview Ave House-4BR/8PPL Retreat

Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

10.0 out of 10, Exceptional, (1)
"Great experience. Very close to a lot of downtown restaurants and Bridgeton. 10 to 15 mnutes from the beach. Lots of added special touches and amenities. Great job by the host."
The price is NZ$299
includes taxes & fees
7 July - 8 July
Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

Upscale 4BR Retreat at the Reservoir!

The price is NZ$1,437
includes taxes & fees
20 July - 21 July
Upscale 4BR Retreat at the Reservoir!

Centric property close to all the great things in the city

8.2 out of 10, Very good, (12)
"This rental was great accommodation"
The price is NZ$498
includes taxes & fees
1 July - 2 July
Centric property close to all the great things in the city

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

The price is NZ$2,435
includes taxes & fees
1 July - 2 July
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Charming 2-bedroom house with WiFi, AC in Fairfield

10.0 out of 10, Exceptional, (1)
"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 NZ$574
includes taxes & fees
1 July - 2 July
Charming 2-bedroom house with WiFi, AC in Fairfield

Marine Theme - 4 BR - Backyard - Fire pit

9.8 out of 10, Exceptional, (6)
"Had a great stay at Sarah’s place. She was very communicative and helpful before and during our stay. The house was nice and large - it was great having two living rooms for our large group. Convenient location close to many stores and sights!"
The price is NZ$839
includes taxes & fees
6 July - 7 July
Marine Theme - 4 BR - Backyard - Fire pit

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
The price is NZ$314
includes taxes & fees
23 July - 24 July
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

10.0 out of 10, Exceptional, (17)
"Very comfortable home. Lots of thought in providing all needed for a stay. We so appreciated the hosts communication...made life pleasant. We will repeat!"
The price is NZ$1,187
includes taxes & fees
6 July - 7 July
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

10.0 out of 10, Exceptional, (5)
"And the bed was confortable"
The price is NZ$973
includes taxes & fees
1 July - 2 July
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

Updated, cozy single family in Fairfield County

9.2 out of 10, Wonderful, (10)
"House was great, hosts were attentive. Enjoyed our stay"
The price is NZ$907
includes taxes & fees
1 July - 2 July
Updated, cozy single family in Fairfield County

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is NZ$4,027
includes taxes & fees
1 July - 2 July
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 NZ$1,228
includes taxes & fees
1 July - 2 July
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (20)
"Easy entrance and exit policy. Great communication from owners. Perfect location. "
The price is NZ$1,844
includes taxes & fees
30 July - 31 July
Waterview House Walking Distance from Cove Beach

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (20)
"Everything was great"
The price is NZ$1,730
includes taxes & fees
1 July - 2 July
Stylish Beach Home near Stamford Downtown/Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is NZ$959
includes taxes & fees
13 July - 14 July
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"Great home with fun ping pong table!"
The price is NZ$2,252
includes taxes & fees
5 July - 6 July
New Beach Home near Stamford Downtown/Shippan

The Luxury downtown. Pool Jim basketball

The price is NZ$423
includes taxes & fees
9 July - 10 July
The Luxury downtown. Pool Jim basketball
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.
Save an average of 15% on thousands of hotels when you're signed in