Discover Your Perfect Westport Vacation Homes

Westport Pet Friendly Vacation Rentals

10.0 (1 Review)
House
Modern Farmhouse
  • Air Conditioner
  • Parking
  • Pet Friendly
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Westport Large Vacation Homes

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Why Choose Rent By Owner for your Westport Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Westport Vacation Rentals

Where are the best neighborhoods to stay in Westport?

When planning your stay in Westport, Connecticut, choosing the right neighborhood can greatly enhance your vacation experience. The area offers charming communities that blend coastal beauty with convenient access to local amenities. Whether you're seeking a peaceful retreat or a lively atmosphere, Westport neighborhoods provide a variety of options to suit your preferences. Exploring different parts of this picturesque town allows you to enjoy the best of Connecticut’s coastal charm while staying comfortably within reach of all the attractions you desire. Booking a well-situated vacation rental in Westport ensures a memorable and stress-free visit to this inviting New England destination.

East Norwalk

This part of the region offers convenient access to local amenities and a tranquil atmosphere, making it a great choice for those seeking a relaxed stay near key attractions. Here, you'll find comfortable vacation rentals that provide both accessibility and comfort in a welcoming neighborhood.

View 81+ Rentals in East Norwalk

Best Times to Visit Westport

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as each season offers unique opportunities to enjoy the natural beauty and local charm of this destination's surroundings.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you'll experience warm weather ideal for outdoor activities and enjoying the coastal scenery here. This is when the area sees many visitors seeking a vibrant, lively atmosphere.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 65°F (18°C)
autumn
Fall (September to November)

Autumn offers stunning foliage and mild weather, making it a popular time to explore local landscapes and enjoy the region's natural beauty. Vacation rentals tend to book quickly during this picturesque season.

Average Temperature Daytime: roughly 70°F (21°C) - Nighttime: around 50°F (10°C)

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and fewer visitors, providing a quieter experience in the area. It's an ideal time to find more affordable vacation rentals and enjoy peaceful surroundings.

Average Temperature Daytime: around 40°F (4°C) - Nighttime: close to 30°F (-1°C)
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Spring (March to May)

Spring ushers in milder weather and blooming landscapes, attracting those looking for a serene getaway. Off-peak rates may be available, making it a good time for budget-conscious travelers.

Average Temperature Daytime: approximately 60°F (16°C) - Nighttime: about 40°F (4°C)

Weekly Weather Forecast for Westport

How to Book Your Westport Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Westport

More Top-Rated Vacation Rentals in Westport Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining spaces perfect for gathering with family and friends amidst scenic views.
  • Take advantage of private gardens or landscaped yards ideal for relaxation or outdoor activities.
  • Make use of spacious decks or patios for sunbathing or watching sunsets over the area’s natural beauty.
  • Benefit from access to swimming pools, whether private or shared, for refreshment during warm months.
  • Explore well-maintained outdoor fireplaces or fire pits, perfect for cozy evenings outdoors.
  • Utilize outdoor grills or barbecue stations to prepare delicious meals while enjoying the fresh air.
  • Experience proximity to beaches or waterfronts, allowing easy access to water-based recreation in this coastal destination.

Top Attractions Around Westport

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and cultural experiences just moments from your vacation rentals, making your stay both relaxing and engaging.

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Family Activities

  • Westport Country Playhouse: Enjoy engaging performances and family-friendly shows at this historic theater, offering a cultural experience in the area.
  • Westport Library Children's Programs: Participate in creative storytimes and educational activities designed to keep young minds entertained and inspired here.
  • Pleasure Point Park: Spend a relaxing day at this scenic waterfront park with playgrounds, picnic spots, and access to the beach for family outings.
  • Compo Beach: Take advantage of the sandy shores and calm waters at this popular Westport destination, ideal for swimming and building sandcastles with your loved ones.
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Adult Activities

  • Visit Westport's Main Street: Explore the charming shops, galleries, and eateries that capture the vibrant local culture of this coastal town.
  • Relax at Compo Beach: Spend a day soaking up the sun or strolling along the scenic shoreline of this popular Connecticut beach destination.
  • Discover the Westport Historical Society: Immerse yourself in the area's rich history through engaging exhibits and well-preserved landmarks.
  • Enjoy a Round of Golf at a Local Course: Tee off amid picturesque surroundings at one of the region's highly-rated golf courses, perfect for leisure and relaxation.

Other Places to Stay in Westport, CT

Earthplace Museum
Earthplace Museum Vacation Rentals
Old Mill Beach
Old Mill Beach Vacation Rentals
Levitt Pavilion
Levitt Pavilion Vacation Rentals
Westport Farmers Market
Westport Farmers Market Vacation Rentals
Westport Historical Society
Westport Historical Society Vacation Rentals
Westport Country Playhouse
Westport Country Playhouse Vacation Rentals
Sherwood Island State Park
Sherwood Island State Park Vacation Rentals
Greens Farms
Greens Farms Vacation Rentals
Rolnick Observatory
Rolnick Observatory Vacation Rentals
Burying Hill Beach
Burying Hill Beach Vacation Rentals
Compo Beach
Compo Beach Vacation Rentals
Alvord Beach
Alvord Beach Vacation Rentals
More Places to Stay Near Westport

Westport Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region’s renowned eateries to experience authentic flavors unique to this destination.
  • Plan Outdoor Activities: Make the most of your stay by engaging in outdoor pursuits such as beaches, parks, or scenic trails that highlight the area's natural beauty.
  • Visit Cultural Attractions: Discover the local art galleries and historical sites that offer insight into the area's rich heritage and vibrant community.
  • Choose Prime Accommodation Locations: Book your vacation rentals strategically situated near key attractions to maximize convenience and enjoyment during your visit.

Transportation Options

  • Westport Transit: The local bus service offers convenient transportation throughout the area, making it easy for you to explore your surroundings without a car.
  • Metro-North Railroad: Commuter trains connect here with New York City and other regional destinations, ideal for day trips or traveling to nearby urban centers.
  • Taxi Services and Rideshares: Reliable taxi companies and popular rideshare options like Uber provide flexible transportation options within the region.
  • Car Rentals: Several rental agencies operate in the area, offering the freedom to explore Westport and its scenic surroundings at your own pace.

Local Customs Options

  • Westport's Maritime Heritage: You’ll find that the local customs here often celebrate the area's rich maritime history through community events and traditions rooted in seafaring life.
  • Charming Main Street Hospitality: Visitors frequently experience the warm, welcoming atmosphere by engaging with shop owners and locals who cherish their town’s friendly community spirit.
  • Seasonal Festivals and Events: Participating in seasonal festivals is a common way for visitors to appreciate the region’s cultural heritage and enjoy the vibrant local community.
  • Artisan Craftsmanship: Supporting local artisans during your stay allows you to immerse yourself in the area's craftsmanship, which is a notable aspect of the regional customs.

Frequently Asked Questions About Westport?

1. What are the top vacation rentals in Westport?

There are a lot of options in Westport. If you plan on staying in the Westport area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Westport:

2. How many vacation rentals have private pools in Westport?

There are 15 vacation rentals with private pools near Westport. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Westport are best for families?

If you are looking for a family-friendly vacation home in Westport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Westport:

4. How many Rentbyowner vacation rentals are available in Westport?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 114 in the Westport area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Westport. 

5. What is the cancellation policy for vacation rentals in Westport, Connecticut?

Cancellation policies vary by listing, so it’s important to review the specific terms provided on each property’s page. You can find detailed information and contact the owner directly to clarify any questions about cancellations.

6. How do I ensure my booking in Westport meets my needs?

You should carefully read the property description, amenities, and reviews before confirming your reservation. If you have special requirements, reach out to the host to confirm that the property suits your needs.

7. Are there additional fees I should be aware of when booking here?

Additional fees such as cleaning charges or service fees are typically outlined in the listing details. Always review these costs before completing your booking to ensure transparency and avoid surprises.

8. What is the process for checking in and out of a vacation rental in this region?

Check-in and check-out procedures are specified in each listing. Communicate with your host beforehand if you have any special requests or need clarification on key collection or departure times.

9. Is it possible to modify or extend my stay at a vacation rental in Westport?

Modifications or extensions depend on the availability of the property and the owner's policies. Contact the host directly through the platform to discuss your plans and confirm if adjustments can be accommodated.