Entire home
Main Street Westport, walk to shops, dining, downtown
Photo gallery for Main Street Westport, walk to shops, dining, downtown





4 bedrooms3 bathroomsSleeps 8
Popular amenities
Explore the area
Westport, CT
- Levitt Pavilion18 min walk
- Westport Country Playhouse2 min drive
- Compo Beach12 min drive
- Norwalk, CT (ORQ-Norwalk Heliport)8 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom #1
1 Queen Bed
Bedroom #2
1 Queen Bed
Bedroom #3
1 Queen Bed
Bedroom #4
1 Queen Bed
3 bathrooms
Hall Bathroom
Bathtub or shower · Toilet
Lower level en Suite
Toilet · Shower only
Primary en Suite
Toilet · Shower only
Spaces
Kitchen
About this property
Main Street Westport, walk to shops, dining, downtown
Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price.
Welcome to The Main Street Stay in charming Westport, CT!
Experience the timeless charm of small-town bliss in this spacious Westport retreat.
Perched above Main Steet, this PRIVATE gem offers modern comforts and serene charm just a short stroll from boutique shopping, local dining and vibrant attractions. With its perfect blend of location and convenience, it’s the ideal getaway for creating lasting memories.
-------------------------
THE SPACE (occupancy 8)
Main Level: Living room, kitchen, dining room and three bedrooms on main level (stairs required)
Discover four fully furnished sleeping quarters for rest and rejuvenation. Spacious and tastefully adorned, these rooms cater to your comfort and individual style. Whether seeking peaceful slumber or personal retreat, these bedrooms fulfill your every need.
Primary Bedroom en Suite: Queen sized bed, dresser, 2 closets, private bathroom with bathtub/shower, and lots of natural light.
Second Bedroom: Queen sized bed, dresser and closet
Third Bedroom: Queen sized bed, dresser and closet
Living Room: At the heart of the home, the living room radiates warmth and hospitality. With comfortable seating and abundant natural light, it's perfect for quiet evenings or gatherings with loved ones.
Kitchen: Fully equipped for culinary adventures including electric stove/oven, microwave, air fryer, dishwasher, Keurig Coffee Maker and so much more. Stocked with pantry essentials.
Gas Grill: Situated on porch located off kitchen.
Bathrooms: Three meticulously designed bathrooms. Crafted with attention to detail, they blend practicality with luxury, modern fixtures, and ample storage. Perfect for quick showers or leisurely soaks, these bathrooms offer the ideal relaxing ambiance. All bathrooms offer complimentary shampoo, conditioner, body wash.
Lower Level:
The lower level has a versatile living space designed for both productivity and relaxation.
Dedicated Office Area: Two desks and chairs, perfect for remote work or study.
Fourth Bedroom: Private, separated from living space by French doors, with full bath and laundry area
Bathroom: Full bath with shower/tub tucked away in the lower level fourth bedroom
Laundry: A full-sized washer and dryer are in the fourth (lower level) bedroom.
Living space: This space is equipped with a cozy couch, additional chairs, a foosball table, and a keyboard, making it a great spot for kids to unwind separately from the rest of the family.
Whether you are working remotely or just looking for a peaceful retreat, this space offers the perfect balance of functionality and comfort.
MODERN AMENITIES:
High-speed internet for connectivity
Full-sized washer and dryer in lower level bedroom
Outdoor Patio/BBQ Grill offers relaxation and recreation opportunities
Large two-car garage available for guest use
High Chair available
Bath amenities left to get you started (toilet paper, shampoo, conditioner and body wash)
GUEST ACCESS
You'll have exclusive access to the entire property during your stay. From the 4 bedrooms and 3 bathrooms to the cozy living room, every corner of this well-appointed space is at your disposal. Feel free to make yourself at home and enjoy all the amenities and comforts this property offers. It's your private sanctuary where you can relax, unwind, and create wonderful memories throughout your stay.
Other things to note
The starter pack will help you get started with your stay and includes one Paper towel, dishwasher pods, dish soap, and a few garbage bags, as well as shampoo, conditioner, and body wash.
For your safety, a security camera are installed at the front door and the front driveway of the property to monitor the exterior for the safety and security of our guests and the premises. There are no cameras or listening devices inside the property.
The camera will be active throughout your stay and is positioned solely for external monitoring and will not compromise your privacy within the accommodation.
It is worth mentioning that the property is situated on a main road, but sits up off of the street. We do want guests to be aware that they will have to back out of the driveway, but can use the neighbors driveway to back out safely.
We can't wait to host you!
NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ARE ALLOWED AT ANY TIME. The maximum number of guests or visitors for this house, as indicated in the listing, should be honored at all times, day or night. These are cause for eviction with no refund and may damage our ability to offer the home to future guests, exposing you to liability. This is a quiet residential neighborhood; please be respectful of the neighbors at all times!
Welcome to The Main Street Stay in charming Westport, CT!
Experience the timeless charm of small-town bliss in this spacious Westport retreat.
Perched above Main Steet, this PRIVATE gem offers modern comforts and serene charm just a short stroll from boutique shopping, local dining and vibrant attractions. With its perfect blend of location and convenience, it’s the ideal getaway for creating lasting memories.
-------------------------
THE SPACE (occupancy 8)
Main Level: Living room, kitchen, dining room and three bedrooms on main level (stairs required)
Discover four fully furnished sleeping quarters for rest and rejuvenation. Spacious and tastefully adorned, these rooms cater to your comfort and individual style. Whether seeking peaceful slumber or personal retreat, these bedrooms fulfill your every need.
Primary Bedroom en Suite: Queen sized bed, dresser, 2 closets, private bathroom with bathtub/shower, and lots of natural light.
Second Bedroom: Queen sized bed, dresser and closet
Third Bedroom: Queen sized bed, dresser and closet
Living Room: At the heart of the home, the living room radiates warmth and hospitality. With comfortable seating and abundant natural light, it's perfect for quiet evenings or gatherings with loved ones.
Kitchen: Fully equipped for culinary adventures including electric stove/oven, microwave, air fryer, dishwasher, Keurig Coffee Maker and so much more. Stocked with pantry essentials.
Gas Grill: Situated on porch located off kitchen.
Bathrooms: Three meticulously designed bathrooms. Crafted with attention to detail, they blend practicality with luxury, modern fixtures, and ample storage. Perfect for quick showers or leisurely soaks, these bathrooms offer the ideal relaxing ambiance. All bathrooms offer complimentary shampoo, conditioner, body wash.
Lower Level:
The lower level has a versatile living space designed for both productivity and relaxation.
Dedicated Office Area: Two desks and chairs, perfect for remote work or study.
Fourth Bedroom: Private, separated from living space by French doors, with full bath and laundry area
Bathroom: Full bath with shower/tub tucked away in the lower level fourth bedroom
Laundry: A full-sized washer and dryer are in the fourth (lower level) bedroom.
Living space: This space is equipped with a cozy couch, additional chairs, a foosball table, and a keyboard, making it a great spot for kids to unwind separately from the rest of the family.
Whether you are working remotely or just looking for a peaceful retreat, this space offers the perfect balance of functionality and comfort.
MODERN AMENITIES:
High-speed internet for connectivity
Full-sized washer and dryer in lower level bedroom
Outdoor Patio/BBQ Grill offers relaxation and recreation opportunities
Large two-car garage available for guest use
High Chair available
Bath amenities left to get you started (toilet paper, shampoo, conditioner and body wash)
GUEST ACCESS
You'll have exclusive access to the entire property during your stay. From the 4 bedrooms and 3 bathrooms to the cozy living room, every corner of this well-appointed space is at your disposal. Feel free to make yourself at home and enjoy all the amenities and comforts this property offers. It's your private sanctuary where you can relax, unwind, and create wonderful memories throughout your stay.
Other things to note
The starter pack will help you get started with your stay and includes one Paper towel, dishwasher pods, dish soap, and a few garbage bags, as well as shampoo, conditioner, and body wash.
For your safety, a security camera are installed at the front door and the front driveway of the property to monitor the exterior for the safety and security of our guests and the premises. There are no cameras or listening devices inside the property.
The camera will be active throughout your stay and is positioned solely for external monitoring and will not compromise your privacy within the accommodation.
It is worth mentioning that the property is situated on a main road, but sits up off of the street. We do want guests to be aware that they will have to back out of the driveway, but can use the neighbors driveway to back out safely.
We can't wait to host you!
NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ARE ALLOWED AT ANY TIME. The maximum number of guests or visitors for this house, as indicated in the listing, should be honored at all times, day or night. These are cause for eviction with no refund and may damage our ability to offer the home to future guests, exposing you to liability. This is a quiet residential neighborhood; please be respectful of the neighbors at all times!
Property manager
iTrip Connecticut-Coast
Premier Host
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning
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- Washer
- Dryer
- Pet-friendly
- Air conditioning
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Westport
Westport is home to this holiday home. Westport Historical Society and Levitt Pavilion are cultural highlights, and some of the area's activities can be experienced at Stepping Stones Museum for Children and Country Club of Fairfield. Looking to enjoy an event or a game while in town? See what's happening at Total Mortgage Arena or Hartford HealthCare Amphitheater.
Westport, CT
What's nearby
- Levitt Pavilion - 18 min walk - 1.5 km
- Westport Country Playhouse - 2 min drive - 1.7 km
- Historic South Norwalk - 8 min drive - 9.2 km
- Norwalk Maritime Aquarium - 8 min drive - 8.9 km
- Compo Beach - 12 min drive - 6.3 km
Getting around
Restaurants
- Bartaco - 15 min walk
- GG & Joe - 11 min walk
- Starbucks - 14 min walk
- The Granola Bar - 2 min drive
- Joe's Pizza & Italian Restaurant - 9 min walk
Frequently asked questions
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About the host
Hosted by iTrip Connecticut-Coast

Premier Host
They consistently provide great experiences for their guests
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