Holiday In The Hamptons - Vacation Rentals in Madison
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Luxury Places to Stay in Madison
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Top-Rated Vacation Rentals with a Pool in Madison
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Pet-Friendly Vacation Rentals in Madison
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Large Vacation Homes & Villas in Madison
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Wheelchair Accessible Vacation Homes in Madison
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Madison Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Madison
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About Madison Vacation Rentals
With more than 188 Madison vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidayinthehamptons and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Madison.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidayinthehamptons Madison, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Madison. Places to stay near Madison are 916.45 ft² on average, with prices averaging US $554 a night.
Holidayinthehamptons makes it easy and safe to find and compare vacation rentals in Madison with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Madison
| Type | Count |
|---|---|
| Vacation Homes | 125 |
| Cottages | 27 |
| Holiday Apartments | 19 |
| Hotels | 7 |
| B&B | 4 |
| Cabin Rentals | 2 |
| Others | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Madison
★ Pro Tip: Holidayinthehamptons makes it easy to compare the best listings on Holidayinthehamptons homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayinthehamptons homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Madison.
Weather in Madison
View the weather forecast for Madison before booking your Madison Vacation Rentals to confirm your best time to go.
Top Attractions Around Madison, CT
Holidayinthehamptons offers a large selection of top attractions around Madison. Research things to do on your vacation before you visit Madison.
Other Places to Stay Near Madison, CT
Complexes around Madison, CT
Madison Vacation Rental Frequently Asked Questions
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:
- The Homestead
- Direct waterfront renovated cottage.
- COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
- Awesome Views of Long Island Sound! Relax, swim, walk and feel the sea breezes!
- TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12
- Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
- Ideal Madison home just steps to the beach
- Great home walkable to everything!
- Charming 2-Bedroom Ranch on a Quiet Cul-de-Sac - Minutes to Beach and Town Green
- The gardners Cottage 1 mile from long Island Sound - pet friendly
How many vacation rentals have private pools in Madison?
There are 5 vacation rentals with private pools near Madison. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Madison?
Currently, the total number of properties listed in 2026 is over 188 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.
