Madison Vacation Homes

A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

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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

Shannon G.

HK$5,245 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

2. Adorable Cottage, 5 min walk to water & town

Westbrook Center

Donovan V.

HK$3,813 total

includes taxes & fees

15 Oct - 16 Oct

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

3. Historic New England home ,Reunions Beach pass

Guilford

Liz H.

HK$5,046 total

includes taxes & fees

13 Oct - 14 Oct

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

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

Old Saybrook

Becky W.

HK$3,535 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Saybrook Manor

Alexis L.

HK$4,416 total

includes taxes & fees

21 Oct - 22 Oct

A stone pier leading to a beach with houses in the background.

6. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

Emily M.

HK$2,136 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Wallingford Center

Jeanette W.

HK$2,289 total

includes taxes & fees

11 Oct - 12 Oct

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

David M.

HK$2,289 total

includes taxes & fees

11 Oct - 12 Oct

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

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

Durham

Iris F.

HK$8,107 total

includes taxes & fees

11 Oct - 12 Oct

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

10. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

Wallace R.

HK$2,497 total

includes taxes & fees

26 Oct - 27 Oct

11. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

Jamie S.

HK$1,785 total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

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

East Lyme

Sarah G.

HK$3,445 total

includes taxes & fees

11 Oct - 12 Oct

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

13. The SandPiper

Pipes Cove

Julian V.

HK$1,937 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a sofa, a dining table, and a massage chair.

14. #29 - Modern 5 Bedroom/2 Bath

Middletown

Gail R.

HK$3,640 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Branford

HK$10,139 total

includes taxes & fees

12 Oct - 13 Oct

16. Family Stays: Middletown, CT

Middletown

Trisha T.

HK$2,111 total

includes taxes & fees

3 Nov - 4 Nov

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

17. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,533 total

includes taxes & fees

3 Nov - 4 Nov

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

18. Aqua Vista

Pipes Cove

Kerri L.

HK$2,511 total

includes taxes & fees

12 Oct - 13 Oct

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

19. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,403 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Pipes Cove

Callie E.

HK$3,022 total

includes taxes & fees

1 Nov - 2 Nov

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Top Madison Hotel Reviews

Cambria Hotel New Haven University Area

10/10 Excellent

"It was very clean and very modern looking we like it a lot"

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