Discover Your Perfect Fairfield County Vacation Homes

Best Vacation Homes in Fairfield County

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9.8 (52 Reviews)
Bed & Breakfast
West Lane Inn
  • Air Conditioner
  • Parking
  • TV
View Availability
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Fairfield County Large Vacation Homes

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Why Choose Rent By Owner for your Fairfield County 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.

Best Times to Visit Fairfield County

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here ensures you experience the best of what this region has to offer, whether you're seeking vibrant local events or peaceful moments in your vacation rentals.

Peak Season Highlights

spring
Spring (March to May)

During this time, the area experiences a burst of natural beauty as flowers bloom and temperatures rise, making it an ideal period for exploring outdoor activities in your vacation rentals.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F
autumn
Fall (September to November)

The region's vibrant foliage creates a picturesque backdrop, attracting visitors who prefer to enjoy crisp air and scenic surroundings from their vacation rentals.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Winter (December to February)

Cold weather and fewer tourists characterize this season, offering a peaceful retreat from the crowds while still providing cozy accommodations for winter enthusiasts.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Summer (June to August)

While summer can be lively, it’s also when the area sees lower occupancy outside peak months, allowing you to enjoy more private and relaxed stays in your vacation rentals.

Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F

Weekly Weather Forecast for Fairfield County

How to Book Your Fairfield County 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 Fairfield County

More Top-Rated Vacation Rentals in Fairfield County 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 with a fully equipped patio or barbecue area.
  • Relax by a private swimming pool or hot tub, perfect for unwinding after exploring the region.
  • Take advantage of expansive lawns or gardens ideal for outdoor activities and gatherings.
  • Benefit from scenic walking or jogging trails directly accessible from your rental.
  • Make use of outdoor fireplaces or fire pits for cozy evenings under the stars.
  • Utilize spacious decks or verandas that offer beautiful views of the surrounding landscape.
  • Engage in recreational sports with access to tennis courts, volleyball nets, or other outdoor amenities nearby.

Top Attractions Around Fairfield County

What attractions are nearby?

Here, you can explore a variety of outdoor activities and cultural attractions that showcase the best of this region’s natural beauty and local heritage while enjoying your stay in nearby vacation rentals.

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Family Activities

  • Stepping Stones Museum for Children: Engage with interactive exhibits designed to inspire learning and creativity for kids of all ages within the region.
  • Connecticut Audubon Society Birdcraft Museum and Sanctuary: Explore family-friendly walking trails and observe local bird species in a peaceful natural setting nearby.
  • The Maritime Aquarium at Norwalk: Discover marine life through hands-on exhibits and captivating animal encounters, perfect for family outings here.
  • Connecticut Botanical Center: Enjoy outdoor exploration and educational programs amidst beautifully maintained gardens that make for a lovely day with your loved ones.
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Adult Activities

  • Wine Tasting Tours: Explore local vineyards and indulge in wine tasting experiences that highlight the region's renowned viticulture.
  • Golfing: Enjoy a round of golf at some of the area's scenic courses, offering stunning views and challenging layouts for enthusiasts.
  • Historic Site Visits: Discover the rich history of this destination by visiting historic landmarks and museums that tell the story of the region.
  • Fine Dining: Savor exquisite culinary offerings at upscale restaurants emphasizing farm-to-table cuisine native to here’s vibrant food scene.

Other Places to Stay in Fairfield County, CT

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Fairfield County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area's attractions with more tranquility and better availability for your preferred vacation rentals.
  • Explore Local Cuisine and Dining Options: Tasting authentic regional flavors enhances your experience, and many rental properties are conveniently located near top local restaurants.
  • Take Advantage of Water Activities and Outdoor Recreation: The region offers a variety of outdoor pursuits that can be easily accessed from your rental, providing memorable adventures amidst natural beauty.
  • Utilize Smart Booking Strategies: Securing your vacation rentals early ensures better choices and competitive rates, allowing you to maximize your stay here with confidence.

Transportation Options

  • Metro-North Railroad: You can easily access commuter rail services connecting to New York City and other parts of the region, making it convenient for day trips or commuting.
  • Connecticut Post Road (Route 1): This major highway offers straightforward driving options through the area, linking you to neighboring towns and local attractions.
  • Bradley International Airport: A primary airport serving the area, providing domestic flights that simplify travel both nationally and internationally.
  • Local Bus Services: Several regional bus operators offer routes around the destination, perfect for exploring nearby communities without needing a car.

Local Customs Options

  • Welcoming Hospitality: You’ll notice a warm and friendly approach from locals, reflecting the region's tradition of hospitality that makes visitors feel at home.
  • Seasonal Celebrations: Participating in seasonal festivals and events is common here, offering you an authentic taste of local customs throughout the year.
  • Community Gatherings: Local community events often center around neighborhood gatherings and farmers' markets, inviting you to engage with residents easily.
  • Respect for Tradition: The area's residents value and preserve their historical customs, which you can observe through various cultural practices and local craftsmanship.

Frequently Asked Questions About Fairfield County?

1. What are the top vacation rentals in Fairfield County?

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

2. How many vacation rentals have private pools in Fairfield County?

There are 100 vacation rentals with private pools near Fairfield County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Fairfield County are best for families?

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

4. How many Rentbyowner vacation rentals are available in Fairfield County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1169 in the Fairfield County 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 Fairfield County. 

5. What is the cancellation policy for booking a vacation rental in Fairfield County?

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the options and any applicable fees.

6. How do I find the best vacation rental deals in the region?

To secure the best deals, compare different listings, check for special offers or discounts, and read reviews to ensure quality and value for your stay.

7. Are there any restrictions on bringing pets to vacation rentals here?

Pet policies are set by individual hosts, so it’s important to read each listing carefully or speak with the owner to confirm if pets are allowed during your visit.

8. What amenities can I expect from vacation rentals in this destination?

Amenities vary across properties, so review each listing’s features such as Wi-Fi, parking, kitchens, and outdoor spaces to find the best fit for your needs.

9. How do I ensure my booking is secure and reliable in this area?

Book only through reputable platforms that offer secure payment options and verified listings to ensure a trustworthy and seamless reservation process.

Fairfield County Top Rated Vacation Rentals

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