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- Rentals by Owner
Discover Your Ideal Fairfield County, Connecticut Rental by Owner for a Comfortable Stay
Discover Your Perfect Fairfield County Rentals by Owner
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Rentals by Owner
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Luxury Vacation Rentals
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Pet Friendly Vacation Rentals
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Unique Vacation Rentals
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Cabin Rentals
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Cottage Rentals
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Ski Chalet Rentals
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Timeshares
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Family Vacation Rentals
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Vacation Rentals with Pools
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Large Group Vacation Rentals
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Sustainable Travel
Fairfield County Rentals by Owner
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- Security/Safety
- Bedding/Linens
- Air Conditioner
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- Balcony/Terrace
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- TV
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- TV
- View
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- View
- Air Conditioner
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- Pool
- Air Conditioner
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- View
- Air Conditioner
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- Pet Friendly
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- Security/Safety
- Child Friendly
- Pet Friendly
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- Bedding/Linens
Why Choose Rent By Owner for your Fairfield County vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Fairfield County
When should you plan your Rentals by Owner stay?
Choosing the right time to vacation here can help you enjoy the region’s best experiences, ensuring your rent by owner booking in Fairfield County, Connecticut, aligns perfectly with your preferred season and weather conditions.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During these months, you can enjoy the region's lush landscapes and pleasant weather, making it an ideal time for outdoor activities and exploring local attractions.
Early Fall (September to October)
This period offers beautiful foliage and comfortable temperatures, perfect for experiencing the area's scenic beauty and vibrant local events.
Off-Season Highlights
Winter (December to February)
The colder months see fewer visitors, providing a peaceful atmosphere for relaxing staycations or enjoying cozy accommodations in the region.
Late Fall (November)
As the leaves fall and temperatures drop, this quieter season offers more affordable rental options and less crowded attractions.
Weekly Weather Forecast for Fairfield County
How to Book Your Fairfield County vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Fairfield County
Common Rentals by Owner Amenities
What amenities can you expect?
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 entertaining with a private patio or deck, perfect for relaxing after exploring the area.
- Take advantage of a spacious backyard ideal for outdoor games and family gatherings.
- Make the most of a well-maintained garden or landscaped yard that adds to your outdoor experience.
- Relax in a hot tub or outdoor spa, offering a soothing retreat under the stars.
- Benefit from access to a swimming pool, whether private or community-based, during your stay.
- Utilize an outdoor grilling area to prepare meals while enjoying the fresh air.
- Experience scenic views from a balcony or veranda that showcases the natural beauty of this destination.
Top Attractions Around Fairfield County
What attractions are nearby?
In this area, you can enjoy a variety of outdoor activities, cultural experiences, and scenic attractions that make it an ideal destination for your stay, all easily accessible from your Rent By Owner rental in Fairfield County.

Family Activities
- Connecticut's Beardsley Zoo: Experience a day of family fun exploring the region’s only zoo, which offers engaging exhibits and interactive animal encounters.
- The Maritime Aquarium at Norwalk: Discover marine life through captivating exhibits and touch tanks that make learning about ocean habitats both fun and educational.
- Fairfield Park & Recreation: Enjoy outdoor activities, playgrounds, and sports facilities perfect for a family outing in the area’s lush green spaces.
- Stepping Stones Museum for Children: Immerse your kids in hands-on science and art exhibits designed to ignite curiosity and foster creativity within the region.
Adult Activities
- Visit the Bruce Museum in Greenwich: Explore engaging art and science exhibits that highlight the region’s rich cultural offerings.
- Enjoy a round of golf at local courses: Tee off at premier golf courses here, perfect for a relaxing day dedicated to your favorite sport.
- Take a scenic hike in the surrounding parks: Discover scenic trails and natural beauty in nearby parks that showcase the area's lush landscapes.
- Experience fine dining in charming local eateries: Savor exquisite cuisine at highly-rated restaurants that capture the essence of this destination's culinary scene.
Other Places to Stay in Fairfield County, CT
Fairfield County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Check out the area's community happenings to immerse yourself in local culture and enjoy free or low-cost entertainment during your stay.
- Utilize Prime Booking Times: Book your rental during off-peak seasons or well in advance to secure the best rates and availability in this popular destination.
- Discover Hidden Gems: Venture beyond typical tourist spots to uncover unique shops, eateries, and scenic spots that showcase the region's authentic charm.
- Plan Transportation Ahead: Consider local transit options or rental vehicles to easily navigate the area and access all its attractions conveniently.
Transportation Options
- Metro-North Railroad: This commuter rail service provides convenient connections from the area to New York City and other parts of Connecticut, making it an ideal transportation option for quick city access.
- Interstate Highway System: Major highways such as I-95 and I-91 offer direct routes for driving around the region, giving you flexibility in exploring Fairfield County at your own pace.
- Local Bus Services: Regional bus services operate throughout the area, providing affordable and reliable transportation for daily commutes and excursions within Fairfield County.
- Private Car Services and Taxis: Numerous private transportation companies offer on-demand rides, ensuring secure and comfortable travel throughout the region.
Local Customs Options
- Local Seafood Dining: You’ll find that enjoying fresh seafood is a cherished tradition here, reflecting the region’s maritime heritage.
- Historic Preservation customs: Respect for historic architecture and landmarks is highly valued, offering you a glimpse into the area's rich history.
- Community Events and Celebrations: Participating in seasonal festivals and local parades allows you to experience the vibrant community spirit of this destination.
- Respect for Nature and Outdoor Activities: The region encourages environmentally conscious outdoor recreation, making it ideal for exploring scenic parks and waterways responsibly.
Frequently Asked Questions About Fairfield County Rentals by Owner
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:
- Lower Lvl Private 2BR/1BA Family/Pet Friendly
- Bright Stylish Chic 4BR 4BA Home Pet Friendly!
- Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!
- Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit
- Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio.more!
- Sunny Westport Studio Apt. Above Historic Mill
- Candlewood Lakefront 3bd/2 bath house w/180 degree views!
- Quaint duplex with private yard. Walk to beach, dining, & shopping!
- Make lifelong memories at this New England Quintessential Country Getaway
- Private French Country Estate-New Canaan CT-Pool-Film Set-August available
2. 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 955 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.
3. What is the cancellation policy for rentals by owner in Fairfield County?
4. How do I communicate with the property owner during my stay in Fairfield County?
5. Are there any additional fees I should be aware of when booking a vacation rental here?
6. What amenities can I expect in a rental by owner in this area?
7. How do I ensure the rental meets my needs before booking?
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