Main Street Westport, walk to shops, dining, downtown provides laundry facilities and more. Stay connected with in-room WiFi.
Reviews
8.88.8 out of 10
Excellent
Entire home
4 bedrooms3 bathrooms
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air-conditioning
Parking available
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
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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.
PET MUST BE APPROVED PRIOR TO BOOKING
We love furry friends, but all pets must be approved before booking. Pets are not allowed on furniture, must be crated if left alone, and you are responsible for cleaning up after them. A pet fee of $20 per pet, per day applies and may be added to your reservation after booking.
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!
IMPORTANT BEFORE BOOKING
- Primary guest must be 25+ years of age
- Family-friendly rental only. No parties, events, or gatherings permitted
- Maximum occupancy must be respected. Only registered guests allowed on the property
Verification & Booking Policy
- Guests may be required to complete ID verification prior to check-in
- Access will not be provided until verification is complete
- Reservations made under false or misleading information may be canceled without refund
Respect for Property & Neighbors
- This home is located in a quiet residential area. Guests are expected to respect the property, follow house rules, and be considerate of neighbors at all times
Failure to follow these guidelines may result in additional charges or removal from the property without refund
Property amenities
Internet
Available in the house: WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee/tea maker
Microwave
Refrigerator
Toaster
Dining
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Towels provided
Living spaces
Dining table
Entertainment
TV
Outdoor areas
Charcoal grill
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the area
Westport is home to this holiday home. Levitt Pavilion and Westport Country Playhouse 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 Hartford HealthCare Amphitheater or Total Mortgage Arena. Visit our Westport travel guide
Is Main Street Westport, walk to shops, dining, downtown pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Main Street Westport, walk to shops, dining, downtown?
On-site parking is available at the 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 2 miles (3 km) of Levitt Pavilion, Westport Country Playhouse and Westport Farmers Market. Old Mill Beach and Rolnick Observatory are also within 3 miles (5 km).
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Main Street Westport, walk to shops, dining, downtown Reviews
Reviews
Excellent
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Beautiful home, great location, communicative hosts…A
Charles H.
Stayed 2 nights in Jun 2025
From a partner site
8/10 Good
Dennis B.
21 May 2025
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
Dennis B.
From a partner site
10/10 Excellent
Julie S.
4 Oct 2025
Family 2025
We enjoyed staying at this property. It had plenty of space for our family. We were in the area to visit our family and it was very near to them. We had everything we needed for our stay. The welcome book and goodies were a nice addition. We were close to shopping for anything we wanted, and lots of different food options as well. The only issue we encountered while there was when all of us (6 total) were there, there was not enough living room furniture for all of us to sit. We managed fine, but there are lots of steps to the property if that were an issue for you. As stated in the listing, the driveway is steep and can be difficult to back out of at time with the traffic. Overall, this was a great property and we would stay again.
Julie
Illinois