Luxury Properties for rent in Madison, Connecticut

Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths,...

Presented by Mel Abbott | William Pitt Sotheby's International Realty

Enjoy the best weeks of summer in Madison in this exceptional, academic rental! Available August 10th, this beautifully-crafted residence offers the ideal blend of comfort and...

Presented by Mel Abbott | William Pitt Sotheby's International Realty

Waterview summer rental available for july only as August is now rented. This quintessential Seasonal Beach Cottage with water views is special The views out over Long Island...

Presented by Todd Gould | William Pitt Sotheby's International Realty

Available for the month of august. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

Available for the month of june. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

Available for the month of july. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

Available early september to the end of may, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

July is available at $20,000/mo. August has been rented. Also available for April, May and June at $12,000/mo. Academic available at $6500/mo. Discover coveted Madison living on a...

Presented by Diana Hartman | William Pitt Sotheby's International Realty

Embrace the serene beauty of Middle Beach with this exquisite academic rental, available from September 15th through May 15th, 2027. This direct waterfront property offers a...

Presented by Sue Knapp | William Pitt Sotheby's International Realty

Available for April, May and June at $12,000/mo. Could be available year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane...

Presented by Diana Hartman | William Pitt Sotheby's International Realty

Year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning...

Presented by Diana Hartman | William Pitt Sotheby's International Realty

Available from early september 2026 to end of may 2027! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

Available for month of june 2026. Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the...

Presented by Kirsten Adams | William Pitt Sotheby's International Realty

Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling...

Presented by Phoebe Schreiner | William Pitt Sotheby's International Realty

Available for the Sept 2026 through June 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout...

Presented by Sue Knapp | William Pitt Sotheby's International Realty