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  5. Rentals by Owner

Discover Your Perfect Madison Rentals by Owner

Madison Rentals by Owner

More Top-Rated Rentals by Owner in Madison Area

Why Choose Rent By Owner for your Madison vacation rental?

What makes our Rentals by Owner 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 Madison Rentals by Owner

Where are the best neighborhoods to stay in Madison?

When exploring Madison, Connecticut, choosing the right neighborhood can greatly enhance your stay. Whether you prefer a peaceful coastal area or a charming residential community, Madison offers a variety of neighborhoods that cater to different preferences. By booking a rental by owner through Rent By Owner in Madison, you gain access to trustworthy and reliable vacation homes in prime locations. Each neighborhood provides its own unique atmosphere, ensuring you find the perfect setting for your visit to this picturesque part of Connecticut. Experience the comfort and convenience of staying in a well-suited neighborhood that complements your travel plans in Madison.

Madison Center

In the heart of the area, Madison Center offers convenient access to local shops and dining options, making it an ideal base for exploring this charming region. Here, you'll find a welcoming community atmosphere combined with easy proximity to scenic spots and cultural experiences.

View 85+ Rentals in Madison Center

Best Times to Visit Madison

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as the region offers different attractions and activities throughout the year that are best enjoyed during specific seasons.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you'll enjoy the region's vibrant atmosphere and pleasant weather, making it ideal for exploring rental properties with beautiful surroundings.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
autumn
Early Fall (September to October)

This time offers stunning fall foliage and mild temperatures, perfect for savoring the area's natural beauty while staying in a comfortable vacation rental.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Mid to Late Winter (January to February)

During the colder months, fewer visitors come here, providing a peaceful retreat with cozy rental options to enjoy the quiet season.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

As the area transitions into spring, you can find good deals on rentals while witnessing the early signs of new growth and awakening nature.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Madison

How to Book Your Madison vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Madison

More Top-Rated Rentals by Owner in Madison Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 a private outdoor patio or deck, perfect for relaxing and unwinding amidst the natural surroundings.
  • Take advantage of spacious yards suitable for outdoor activities or gatherings with family and friends.
  • Make the most of direct access to scenic walking or biking trails nearby, ideal for exploring the region’s outdoor beauty.
  • Experience a calming waterfront view if your rental is close to lakes or the shoreline, providing a serene backdrop for your stay.
  • Utilize outdoor dining areas, such as picnic tables or barbecue grills, for al fresco meals under the open sky.
  • Benefit from well-maintained gardens or landscaped grounds that enhance the outdoor experience during your visit.
  • Capitalize on available outdoor leisure facilities like fire pits or hammocks for cozy evenings and restful moments.

Top Attractions Around Madison

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities and scenic explorations that showcase the natural beauty of this destination, making it an ideal spot for relaxing days and memorable adventures during your stay.

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Family Activities

  • Hammonasset Beach State Park: Relax and enjoy a family picnic, leisurely walk along the sandy shores, or explore the scenic nature trails within this popular Connecticut state park.
  • Mystic Seaport Museum: Discover maritime history and engage in interactive exhibits that captivate children and adults alike at this engaging seaside museum nearby.
  • Booker T. Washington Park: Play, cycle, or unwind in this spacious park offering playgrounds and open green areas perfect for family outings by the water.
  • Stony Creek Quarry Adventure & Nature Park: Experience outdoor adventure with hiking, rock climbing, and exploring the natural beauty of this unique park setting here in the region.
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Adult Activities

  • Explore the Madison Beach: Enjoy a relaxing day soaking up the sun or strolling along the pristine sands in this picturesque coastal area.
  • Visit the Madison Art Cinemas: Experience independent films and indie features at a charming local theater, perfect for a cozy evening out.
  • Hike the Hammonasset River Trail: Discover scenic views and native wildlife as you walk through lush landscapes just outside the town center.
  • Enjoy Watersports on Long Island Sound: Engage in kayaking, paddleboarding, or sailing to make the most of the region’s inviting waters.

Other Places to Stay in Madison, CT

Hammonasset Beach State Park
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Madison Center
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Madison Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the area's parks and beaches to enjoy scenic views and outdoor recreation during your stay.
  • Visit nearby dining establishments: Savor regional flavors by exploring restaurants and cafes that showcase the region’s culinary delights.
  • Plan day trips around the region: Discover neighboring towns and attractions to make the most of your visit and experience the area's diversity.
  • Utilize local resources and tips: Connect with hosts or look for insider advice to uncover hidden gems and enhance your experience here.

Transportation Options

  • Madison Train Station: An ideal option for convenient travel to nearby cities and exploring the region's scenic beauty.
  • Local Bus Services: Reliable public transportation that connects various parts of the area, making it easy to reach your rental and local attractions.
  • Taxi and Rideshare Services: Flexible and on-demand options available to help you navigate here without hassle.
  • Car Rentals: Several rental agencies provide vehicles for exploring the wider Connecticut coastline and surrounding attractions at your own pace.

Local Customs Options

  • Local Seafood Dining Customs: You’ll find that enjoying fresh, locally caught seafood is a cherished tradition here, reflecting the area’s coastal heritage.
  • Historical Preservation Practices: Respect for historical sites and preservation efforts are prominent, highlighting the community’s pride in maintaining its regional history.
  • Community Events and Festivals: Participating in seasonal festivals and local events offers a great way to immerse yourself in the region’s friendly and welcoming culture.
  • Environmental Stewardship: The area values sustainable living practices, so you'll notice many initiatives aimed at protecting the natural beauty of the region.

Frequently Asked Questions About Madison Rentals by Owner

1. What are the top vacation rentals in Madison?

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

2. How many Rentbyowner vacation rentals are available in Madison?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 64 in the Madison 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 Madison. 

3. What is the cancellation policy for a rental by owner in Madison, Connecticut?

The cancellation policy varies depending on the individual listing. You should review the specific rental's cancellation terms listed on the property page or contact the owner directly to understand any fees or restrictions before booking.

4. How do I communicate with the owner of a rental in Madison, Connecticut, before booking?

You can reach out to the owner through the messaging feature provided on the Rent By Owner platform. It's recommended to ask any questions regarding the property, availability, and amenities to ensure it meets your needs.

5. Are there any additional fees associated with booking a rental by owner in this area?

Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing details. Be sure to read all the information provided or contact the owner for clarification prior to confirming your reservation.

6. What amenities are usually included in rentals by owner in this region?

Listings often feature amenities like Wi-Fi, parking, kitchen facilities, and outdoor spaces. However, amenities vary by property, so check each listing carefully to confirm what is included during your stay.

7. Is there a specific check-in and check-out process for rentals in Madison, Connecticut?

Check-in and check-out procedures are specified by each owner in the listing. Details may include key pickup, self-check-in options, or personalized arrangements. Contact the owner directly if you need further clarification about the process.

More Rentals You May Like Near Madison

More Top-Rated Rentals by Owner in Madison Area