Madison Vacation Home Rentals from CA $113: Search Top Private Vacation Homes for Rent

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Our top choices for Madison vacation 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.

CA $873 total

includes taxes & fees

Dec 1 - Dec 2

A modern living room with a large TV, white cabinetry, and a view of the outdoors.

2. Charming beach home, complete with pool & cozy guest house!

Clinton

Juliana A.

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

Dr. Maureen C.

CA $877 total

includes taxes & fees

Nov 16 - Nov 17

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

Karol T.

CA $649 total

includes taxes & fees

Nov 15 - Nov 16

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.

CA $785 total

includes taxes & fees

Nov 16 - Nov 17

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.

CA $424 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Wallingford

Alan

CA $424 total

includes taxes & fees

Dec 9 - Dec 10

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

8. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

Jamie S.

CA $299 total

includes taxes & fees

Dec 2 - Dec 3

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.

CA $1,621 total

includes taxes & fees

Nov 14 - Nov 15

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

10. 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.

CA $664 total

includes taxes & fees

Nov 20 - Nov 21

A tranquil beach with stunning ocean views.

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

East Lyme

Sarah G.

CA $470 total

includes taxes & fees

Dec 1 - Dec 2

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

12. The SandPiper

Pipes Cove

Manuela C.

CA $344 total

includes taxes & fees

Nov 30 - Dec 1

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

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

East Lyme

CA $232 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Branford

CA $1,754 total

includes taxes & fees

Nov 16 - Nov 17

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

15. Beach Block Hideaway

Pipes Cove

Teresa C.

CA $608 total

includes taxes & fees

Nov 15 - Nov 16

16. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

Wallace R.

CA $433 total

includes taxes & fees

Nov 30 - Dec 1

17. Family Stays: Middletown, CT

Middletown

Audrey F.

CA $360 total

includes taxes & fees

Nov 16 - Nov 17

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.

CA $494 total

includes taxes & fees

Nov 16 - Nov 17

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

19. Aqua Vista

Pipes Cove

Carey D.

CA $342 total

includes taxes & fees

Nov 18 - Nov 19

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

20. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

CA $412 total

includes taxes & fees

Nov 16 - Nov 17

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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.

See all hotels in Madison

A coastal scene with a stone breakwater extending into the sea, a clear sky with wispy clouds, and a calm ocean.

Top reviews in Madison

The Scranton Seahorse Inn

Madison Center

10/10 Excellent

Francd

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Our stay was great! My flight got in early, and the innkeeper was very kind to let me check in early. The room was clean, comfortable, and safe. The doors to the inn are locked with a keypad that every traveler has a unique code for safety. The first floor common area has a guestbook, a cabinet full of puzzles and other games, a TV, a kitchenette, and lots of seating. The kitchen has a large refrigerator that guests can access along with coffee, tea, and glassware. They also provide postcards...

Casey