Entire home

Main Street Westport, walk to shops, dining, downtown

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

Welcome to Main Street Stay!  Bright and open living space showcasing the seamless flow between the living room, dining area and kitchen
Enjoy the scenic beauty of Compo Beach, just a short drive away - your perfect spot for relaxation and coastal charm in Westport
Spacious patio with gas grill, perfect for outdoor dining and enjoying the fresh air during your stay
Unwind with your favorite shows or movies on the smart TV in this inviting living space
Show off your competitive spirit with a fun game of foosball in the lower-level lounge area

Reviews

9.0 out of 10
Wonderful
4 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Dryer
  • Kitchen
  • Pet-friendly
  • Air conditioning

Explore the area

Map
Westport, CT
  • Levitt Pavilion
    ‪16 min walk‬
  • Westport Country Playhouse
    ‪17 min walk‬
  • Compo Beach
    ‪8 min drive‬
  • Bridgeport, CT (BDR-Igor I. Sikorsky Memorial)
    ‪24 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

bedroom

1 Queen Bed

bedroom

1 Double Bed

bedroom

1 Double Bed

bedroom

1 Double 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

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.

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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.

Charcoal 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!

Property manager

iTrip Connecticut-Coast
Premier Host
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Amenities

Kitchen
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

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.
Map
Westport, CT

What's nearby

  • Levitt Pavilion - 16 min walk - 1.3 km
  • Westport Country Playhouse - 17 min walk - 1.5 km
  • Compo Beach - 8 min drive - 6.3 km
  • Norwalk Maritime Aquarium - 9 min drive - 9.5 km
  • Fairfield University - 13 min drive - 14.8 km

Getting around

  • Westport Station - 5 min drive
  • Bridgeport, CT (BDR-Igor I. Sikorsky Memorial) - 28 min drive

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

Is Main Street Westport, walk to shops, dining, downtown pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Main Street Westport, walk to shops, dining, downtown?

Check-in begins at 4:00 PM.

What time is check-out at Main Street Westport, walk to shops, dining, downtown?

Checkout is at 10:00 AM.

Where is Main Street Westport, walk to shops, dining, downtown located?

Situated in Westport, this holiday home is within 1 mile (2 km) of Westport Historical Society and Levitt Pavilion. Westport Country Playhouse and Earthplace Museum are also within 2 miles (3 km).

Reviews

9.0

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 1 out of 2 reviews
Rating 8 - Good. 1 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Charles H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect spot!

Beautiful home, great location, communicative hosts…A
Stayed 2 nights in Jun 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Dennis B.

Wesport house

It’s a good house - very basic - but gets job done - tricky driveway & noise from road is thing - we did not spend much time in house so was not much of factor Property managers were very helpful supportive

About the host

Hosted by iTrip Connecticut-Coast

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Premier Host

They consistently provide great experiences for their guests