Madison Holiday Homes from £125: Search Holiday Homes in Madison

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Our top choices for Madison holiday homes

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

1. Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

Morgan M.

includes taxes & fees

17 Nov - 18 Nov

A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

2. Historic New England home ,Reunions Beach pass

Guilford

Dr. Maureen C.

includes taxes & fees

16 Nov - 17 Nov

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

3. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

Karol T.

includes taxes & fees

15 Nov - 16 Nov

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

4. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

Alexis L.

includes taxes & fees

15 Nov - 16 Nov

A marina with multiple docks and boats, surrounded by residential buildings and greenery.

5. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

Wallace R.

includes taxes & fees

30 Nov - 1 Dec

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

6. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

includes taxes & fees

16 Nov - 17 Nov

7. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

Jamie S.

includes taxes & fees

30 Nov - 1 Dec

A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

8. Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford

Alan

includes taxes & fees

9 Dec - 10 Dec

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

9. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

Cindy M.

includes taxes & fees

20 Nov - 21 Nov

A cozy living room with a sofa, a coffee table, and a dining area with chairs.

10. NEW private studio 1.1 miles to beach in East Lyme

East Lyme

Agatha C.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a central island, bar stools, and pendant lighting.

11. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham

Iris F.

includes taxes & fees

15 Nov - 16 Nov

A tranquil beach with stunning ocean views.

12. The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

Sarah G.

includes taxes & fees

1 Dec - 2 Dec

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

13. The SandPiper

Pipes Cove

Manuela C.

includes taxes & fees

30 Nov - 1 Dec

A wooden deck with a table and chairs, overlooking a river and trees.

14. Steps to Beach • Hot Tub • Game Room • Water Views

Branford

includes taxes & fees

16 Nov - 17 Nov

15. Family Stays: Middletown, CT

Middletown

Audrey F.

includes taxes & fees

16 Nov - 17 Nov

A wooden pathway leading to a beach with scattered rocks and greenery.

16. Beach Block Hideaway

Pipes Cove

Teresa C.

includes taxes & fees

15 Nov - 16 Nov

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

17. Aqua Vista

Pipes Cove

Carey D.

includes taxes & fees

18 Nov - 19 Nov

A beach with people relaxing, a pier extending into the water, and a clear sky.

18. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

includes taxes & fees

15 Nov - 16 Nov

An outdoor dining area with hanging lights, palm trees, and a bar.

19. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a stainless steel refrigerator, wooden beams, a dining area with a table and chairs, and a large window with blinds.

20. Coastal Landing Stay

East Shore

includes taxes & fees

17 Nov - 18 Nov

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Learn more about Madison

Stroll the soft sand of Hammonasset Beach State Park where locals gather to swim and watch spectacular sunsets. Explore the charming town centre with its independent bookshops, seafood restaurants, and seasonal farmers' markets just steps from Long Island Sound.

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