Discover Your Perfect Fairfield Vacation Homes

Fairfield Luxury Rentals

New
Cottage
Waterfront
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
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Fairfield Pet Friendly Vacation Rentals

8.6 (320 Reviews)
House
The Inn at Fairfield Beach
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
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Fairfield Large Vacation Homes

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Why Choose Rent By Owner for your Fairfield 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 Fairfield Vacation Rentals

Where are the best neighborhoods to stay in Fairfield?

Choosing the right neighborhood in Fairfield, Connecticut, is essential to creating a memorable stay. Whether you're seeking a peaceful area near scenic waterfronts or a lively community close to local amenities, Fairfield offers diverse options for every traveler. Each neighborhood provides unique charm and easy access to the best attractions, making it simple to find the perfect setting for your vacation. When planning your visit, consider the distinct neighborhoods in Fairfield to enjoy a comfortable and convenient experience during your time in this welcoming coastal town.

West End - West Side

This neighborhood offers easy access to urban amenities while providing a comfortable and convenient place to stay in Fairfield. You’ll find a blend of local charm and accessibility, making it ideal for exploring the surrounding region.

View 184+ Rentals in West End - West Side

Greenfield Hill

Known for its picturesque rural setting, Greenfield Hill provides a peaceful retreat within the area, perfect for those seeking tranquility and scenic views. It’s an excellent choice for a relaxing stay surrounded by natural beauty.

View 89+ Rentals in Greenfield Hill

Brooklawn - St. Vincent

Situated close to local attractions, this neighborhood combines community warmth with convenient access to Fairfield's attractions. It’s ideal for travelers looking for a comfortable and connected stay here.

View 169+ Rentals in Brooklawn - St. Vincent

Best Times to Visit Fairfield

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation in Fairfield involves considering seasonal weather patterns and local events, ensuring you enjoy a memorable stay in this charming destination while making the most of your booking experience here.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this area experiences warm weather and longer daylight hours, making it an ideal season for outdoor activities and enjoying local events.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to November)

The vibrant fall foliage attracts visitors seeking scenic views and pleasant weather, perfect for exploring this destination's charming surroundings.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

Snowfall and colder temperatures characterize this season, offering a quieter atmosphere for those looking to enjoy a peaceful retreat.

Average Temperature Daytime: 34°F to 42°F - Nighttime: 25°F to 30°F
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Spring (March to May)

Early spring sees milder weather and blooming landscapes, though occasional rain may bring fewer visitors during this time.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Fairfield

How to Book Your Fairfield 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

More Top-Rated Vacation Rentals in Fairfield 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 relaxing outdoor seating areas perfect for unwinding after a day of exploring the region.
  • Take advantage of well-maintained patios or decks ideal for outdoor dining and entertaining.
  • Make use of private backyard spaces that provide a peaceful retreat surrounded by natural beauty.
  • Benefit from access to outdoor grills for preparing meals during your stay in this destination.
  • Discover spacious lawns and gardens that are perfect for outdoor activities and family fun.
  • Utilize outdoor fireplaces or fire pits to gather with loved ones on cooler evenings.
  • Explore nearby walking trails or scenic paths that offer a great way to experience the area's natural environment.

Top Attractions Around Fairfield

What attractions are nearby?

In this charming destination, you can explore beautiful beaches, enjoy scenic parks, and discover local cultural attractions that offer a relaxing and engaging experience just moments from your Fairfield vacation rentals.

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Family Activities

  • Fairfield Museum and History Center: Explore engaging exhibits and learn about the area's rich history in this family-friendly museum.
  • South Benson Park: Enjoy outdoor activities, playgrounds, and picnicking in this scenic park perfect for family outings in the region.
  • Sunset Hill Park: Experience beautiful views, walking trails, and open spaces to relax and play with your loved ones here.
  • Connecticut Audubon Birdcraft Museum: Discover local bird species and participate in educational programs suitable for all ages in nearby Fairfield.
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Adult Activities

  • Visit the Fairfield Museum and History Center: Explore local history exhibits that offer insight into the area's rich heritage, perfect for an enriching day out.
  • Enjoy a round at the Pequonnock River Golf Course: Perfect your swing at this well-maintained course nestled in the region's scenic surroundings.
  • Relax at Jennings Beach: Spend leisurely hours soaking up the sun or strolling along the shoreline in this popular coastal spot.
  • Discover vibrant art at the Fairfield Arts Council: Engage with local creative talents through exhibitions and cultural events held throughout the year.

Other Places to Stay in Fairfield, CT

Fairfield University
Fairfield University Vacation Rentals
Bellarmine Museum of Art
Bellarmine Museum of Art Vacation Rentals
Regina A. Quick Center for the Arts
Regina A. Quick Center for the Arts Vacation Rentals
South Benson Marina
South Benson Marina Vacation Rentals
Connecticut Audubon Birdcraft Museum
Connecticut Audubon Birdcraft Museum Vacation Rentals
Fairfield Medicine
Fairfield Medicine Vacation Rentals
Fairfield Theater Company
Fairfield Theater Company Vacation Rentals
Jennings Beach
Jennings Beach Vacation Rentals
Fairfield Museum and History Center
Fairfield Museum and History Center Vacation Rentals
Penfield Beach
Penfield Beach Vacation Rentals
Fairfield Beach
Fairfield Beach Vacation Rentals
Pine Creek Par 3 Golf Course
Pine Creek Par 3 Golf Course Vacation Rentals
More Places to Stay Near Fairfield

Fairfield Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the area's charming parks and waterfront spots to relax and enjoy the natural beauty surrounding your vacation rental.
  • Sample Regional Cuisine: Discover local dining options that showcase the region's fresh seafood and classic American dishes, enhancing your stay here.
  • Plan for Seasonal Events: Check out seasonal festivals and community events to immerse yourself in the local culture during your visit.
  • Utilize Nearby Amenities: Make the most of nearby shopping centers, fitness facilities, and entertainment venues to add convenience and entertainment to your trip.

Transportation Options

  • Fairfield Metro Railroad Station: Provides convenient rail service connecting you directly to New York City and other regional destinations, making travel easy from here.
  • Interstate 95: Offers quick access for driving throughout the area and along the East Coast, ideal for exploring Fairfield and beyond by car.
  • Shuttle Services: Local shuttle options transport you between key locations within the region, ensuring hassle-free movement during your stay.
  • Public Bus Transit: Connects various parts of the area, allowing you to navigate Fairfield effortlessly without a vehicle.

Local Customs Options

  • Local Seafood Cuisine: You’ll find that enjoying fresh, locally-sourced seafood is a cherished custom in this area, reflecting its coastal heritage.
  • Historical Preservation: Respect for the region’s history is evident through community efforts to preserve historic sites and architecture, offering you a glimpse into its rich past.
  • Seasonal Festivals: Participating in seasonal festivals and community events is a common tradition, allowing visitors to experience local culture firsthand.
  • Maritime Traditions: Embracing maritime customs such as boating and fishing demonstrates the area's longstanding relationship with the sea, creating authentic experiences for travelers.

Fairfield Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Fairfield?

There are a lot of options in Fairfield. If you plan on staying in the Fairfield 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:

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

There are 2 vacation rentals with private pools near Fairfield. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Fairfield, 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:

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 131 in the Fairfield 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. 

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

The cancellation policy varies depending on the specific property listing. You should review the property's cancellation terms carefully before booking or contact the owner directly for detailed information.

6. How do I confirm my reservation and what are the payment options?

Reservation confirmation typically occurs after completing the online booking process and submitting payment through the platform. Payment methods can include credit cards or other accepted electronic options; details will be provided during the booking process.

7. Are there any additional fees or charges I should be aware of when booking a rental here?

Additional fees such as cleaning fees, service charges, or taxes may apply depending on the property. These will be displayed during the booking process, so review the total costs before confirming your reservation.

8. What amenities are usually included in Fairfield vacation rentals, and how can I find this information?

Amenities vary by property but often include essentials like free Wi-Fi, parking, and kitchen facilities. For precise details, consult the property listing or reach out to the owner to ensure the amenities meet your needs.

9. Is it possible to extend my stay or make changes to my booking once confirmed?

Modifications or extensions depend on the availability and the owner's policies. Contact the property owner directly through the platform to discuss possible adjustments and ensure they can accommodate your request.