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Madison Luxury Rentals

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Madison Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Madison 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 Madison Vacation Rentals

Where are the best neighborhoods to stay in Madison?

Discover the charm of Madison, Connecticut, as you consider where to stay during your visit. This picturesque New England town offers a variety of neighborhoods, each with a unique atmosphere that caters to different travel preferences. Whether you prefer the serene seaside surroundings or the quaint, historic districts, Madison provides a welcoming environment for your vacation. Choosing a neighborhood in Madison ensures you are close to local attractions, beaches, and scenic spots, making it easy to create memorable experiences. Experience the best of this coastal community by selecting a comfortable and conveniently located vacation rental that suits your needs.

Madison Center

Staying near the heart of this destination offers convenient access to local shops and dining, providing an authentic experience of the area's charming atmosphere. Here, you'll find a variety of vacation rentals that make exploring the region effortless and enjoyable.

View 84+ Rentals in Madison Center

Best Times to Visit Madison

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this charming area can enhance your experience, as each season offers unique opportunities to enjoy the region’s scenic beauty and local ambiance.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During the late spring to early summer months, this region experiences its most vibrant and welcoming atmosphere, making it an ideal time for enjoying outdoor activities and scenic views.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F
autumn
Early Fall (September to October)

The early fall season offers pleasant weather and stunning foliage, offering a picturesque setting perfect for exploring and relaxing in this destination's natural beauty.

Average Temperature Daytime: around 65°F to 70°F - Nighttime: around 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

During the winter months, the area sees fewer visitors, providing a quieter atmosphere where you can enjoy a cozy retreat amid serene surroundings.

Average Temperature Daytime: around 35°F to 40°F - Nighttime: around 20°F to 25°F
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Late Autumn (November)

Late autumn is considered off-peak, when the leaves have fallen, and the region quiets down, offering a peaceful environment for those seeking solitude and tranquility.

Average Temperature Daytime: around 50°F to 55°F - Nighttime: around 35°F to 40°F

Weekly Weather Forecast for Madison

How to Book Your Madison 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 Madison

More Top-Rated Vacation Rentals in Madison 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 summer meals with views of the surrounding nature.
  • Relax in a private backyard with lush landscaping and comfortable seating areas.
  • Take advantage of a spacious deck or patio ideal for entertaining friends and family.
  • Make the most of a fire pit for cozy evenings under the stars, a popular feature in the area.
  • Explore well-maintained gardens that add to the natural beauty of your stay.
  • Use a dedicated outdoor grilling station to prepare delicious meals during your visit.
  • Stroll through scenic walking paths or access nearby outdoor recreation spots easily from here.

Top Attractions Around Madison

What attractions are nearby?

During your stay, you can enjoy a variety of outdoor activities and scenic explorations nearby, making it an ideal destination for those seeking both relaxation and adventure in this charming coastal region.

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Family Activities

  • Hammonasset Beach State Park: Spend a day at this popular Connecticut state park, where you can enjoy swimming, picnicking, and exploring nature along the sandy shoreline.
  • Madison Art Cinemas: Experience family-friendly movies in a cozy setting, making for a perfect indoor activity during your stay here.
  • Devil's Hopyard State Park: Discover hiking trails, waterfalls, and scenic views that make this outdoor destination ideal for adventurous families exploring the region.
  • Madison Beach Marina: Take part in boating or paddleboarding adventures on the water, offering memorable experiences for all ages in the area.
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Adult Activities

  • Visit the Madison Beach Hotel: Experience luxurious seaside relaxation and scenic ocean views at this renowned hotel in the region.
  • Explore Hammonasset Beach State Park: Enjoy walking along pristine sands, swimming, or picnicking at this popular Connecticut destination for outdoor enthusiasts.
  • Discover local art galleries and studios: Immerse yourself in the vibrant arts scene that showcases the creative spirit of the area’s talented artists.
  • Enjoy kayaking or paddleboarding on nearby waters: Engage in water sports that offer a refreshing way to explore the scenic coastline here.

Other Places to Stay in Madison, CT

Hammonasset Beach State Park
Hammonasset Beach State Park Vacation Rentals
Hammonasset Beach
Hammonasset Beach Vacation Rentals
Meigs Point Nature Center
Meigs Point Nature Center Vacation Rentals
Madison Center
Madison Center Vacation Rentals
Deacon John Grave House
Deacon John Grave House Vacation Rentals
Anna Mia's
Anna Mia's Vacation Rentals
RJ Julia Booksellers
RJ Julia Booksellers Vacation Rentals
Scranton Memorial Library
Scranton Memorial Library Vacation Rentals
Allis-Bushnell House and Museum
Allis-Bushnell House and Museum Vacation Rentals
North Madison Shopping Center
North Madison Shopping Center Vacation Rentals
More Places to Stay Near Madison

Madison Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Take advantage of the pristine shoreline by spending time at nearby beaches to enjoy relaxing seaside activities and breathtaking views.
  • Visit Scenic Trails: Discover the area's natural beauty through its well-maintained hiking and biking trails, perfect for outdoor enthusiasts seeking adventure.
  • Dine at Local Eateries: Savor regional flavors by dining at popular local restaurants that showcase the region’s culinary diversity.
  • Plan Seasonal Activities: Align your visit with seasonal events and festivals to experience the area's vibrant community spirit and cultural offerings.

Transportation Options

  • Madison Train Station: The train station offers convenient rail connections to nearby cities, making it easy for you to explore the region without hassle.
  • Local Bus Services: Local bus routes provide affordable and reliable transportation options within the area, ideal for short trips around Madison.
  • Rental Car Services: Several rental car agencies operate nearby, giving you the flexibility to discover the surrounding Connecticut coastline and towns at your own pace.
  • Taxis and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available here, offering a quick and comfortable way to get around during your stay.

Local Customs Options

  • Traditional Clambakes: Participating in local clambakes offers a genuine taste of this region's maritime heritage, often held during community gatherings here.
  • Seafood Etiquette: Respect for fresh seafood, especially oysters and lobster, is deeply rooted, and you'll find locals appreciate proper handling and dining manners at the region’s eateries.
  • New England Hospitality: Warm welcomes and friendly interactions reflect the area's cherished tradition of neighborliness, making your stay more comfortable and authentic.
  • Historic Preservation Customs: Appreciating the effort to maintain historical sites and architecture here shows your respect for the area's rich cultural history during your visit.

Frequently Asked Questions About Madison?

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. Which vacation homes in Madison are best for families?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 84 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. 

4. What is the cancellation policy for vacation rentals in Madison, Connecticut?

Cancellation policies vary by property, so you should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations in this area.

5. How do I confirm my booking for a vacation rental in Madison, Connecticut?

Once you select your preferred property, you'll typically need to complete the reservation process on the listing page, which may include providing payment details and contacting the property owner if necessary, to ensure your booking is secure.

6. Are there any house rules or restrictions I should be aware of before booking?

Yes, each vacation rental has its own set of house rules and restrictions listed in the property details. It’s important to read these carefully and reach out to the owner if you have any questions or special requests.

7. What amenities can I expect when booking a vacation rental here?

Amenities vary from property to property, but many here offer essentials like Wi-Fi, parking, and fully equipped kitchens. Check the individual listing for specific amenities available during your stay.

8. How do I find the most suitable vacation rental in Madison, Connecticut for my needs?

You can filter search results based on your preferences, such as size, price range, and desired amenities. Additionally, reading reviews and contacting property owners can help you choose the best option for your visit to the region.