Madison Holiday Rentals from NZ$355: Search Short-Term Rentals

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Our top choices for Madison holiday rentals

A beach with a house in the background, a clear sky, and a calm sea.

1. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

includes taxes & fees

7 Oct - 8 Oct

A living room with a dark grey sofa, two wooden chairs, a small table with a tray, and a large window with a view of the sea.

2. Direct waterfront renovated cottage.

Madison Center

Russell A.

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

27 Oct - 28 Oct

A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

4. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Mary S.

includes taxes & fees

7 Oct - 8 Oct

A cabin with a dining table set for two, a bicycle, and a small porch area.

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Melissa

includes taxes & fees

28 Oct - 29 Oct

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

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

Westbrook Center

Donovan V.

includes taxes & fees

15 Oct - 16 Oct

A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

7. Adorable Cottage with Cottage porch, walk to water & town

Westbrook Center

Kevin K.

includes taxes & fees

30 Sept - 1 Oct

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

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

Old Saybrook

Becky W.

includes taxes & fees

1 Oct - 2 Oct

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

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

Westbrook

Shannon G.

includes taxes & fees

27 Oct - 28 Oct

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

10. Historic New England home ,Reunions Beach pass

Guilford

Liz H.

includes taxes & fees

30 Sept - 1 Oct

A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

11. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Haddam

Kristy C.

includes taxes & fees

19 Oct - 20 Oct

A large, white, multi-story building with a prominent tower and a flag on top.

12. Walk To Goodspeed Opera House!

East Haddam

Anonymous traveller

includes taxes & fees

26 Oct - 27 Oct

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

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

Saybrook Manor

Alexis L.

includes taxes & fees

30 Sept - 1 Oct

A modern house with a deck, outdoor seating, and a fire pit.

14. North Fork Resort

Greenport

Harold

includes taxes & fees

13 Oct - 14 Oct

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

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

Wallingford Center

Jeanette W.

includes taxes & fees

5 Oct - 6 Oct

A rocky shoreline with a beach and ocean in the background.

16. The Stern at Soundview · Beach+Ocean+Sunrise

Old Lyme

"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."

Janine

includes taxes & fees

30 Sept - 1 Oct

A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

17. All New Fully Furnished Cozy Studio

Wallingford Center

Rick C.

includes taxes & fees

4 Oct - 5 Oct

A rocky shoreline with a clear view of the ocean and a distant shoreline with buildings.

18. Keel at Soundview · Beach+OceanView+Sunrise

Old Lyme

Joseph O.

includes taxes & fees

30 Sept - 1 Oct

A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

19. 2BR Apartment Near Wesleyan 301

Washington Street Historic District

Joanne L.

includes taxes & fees

1 Oct - 2 Oct

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

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

Old Lyme

Emily M.

includes taxes & fees

30 Sept - 1 Oct

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Top Madison Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Although a budget property, staff was helpful and the property is well-maintained. We were pleasantly surprised by the quality of our stay."

New Madison beach house - Ocean front- Great views- booking Summer 2026

10/10 Excellent

"The photos don’t do this beachfront property justice. Stunning water views on all sides of the house. Darling little towns dot the shoreline. We had lots to do with kids aged 18 months to 7 years, even with the rain. We stayed there during a nor’easter storm, Joe was the perfect host. Quickly jumped in to get the city to move a downed tree, gave us flexibility with check in time to accommodate flights. Highly recommend!"

Find out more about Madison

Everything you need to know about Madison holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison holiday rentals we have selected for you start as low as NZ$355 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to RJ Julia Booksellers, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Madison. Make sure you have time to check out the aquarium and waterfront during your trip.

What are some of the best holiday rentals that Madison has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated holiday home rental in Madison is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Madison is Waterfront Estate Home - Pool and Private Beach Pavilion - East.

How many holiday rentals are there in Madison?

With 36 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What’s there to see and do in Madison?

Hammonasset Beach and Meigs Point Nature Center are a couple of scenic spots to enjoy the outdoors, whereas Allis-Bushnell House and Museum is one of the cultural attractions. Hammonasset Beach State Park and Madison Green Historic District are other places to visit while you're in town.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.

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Check prices for these dates

Our top choices for Madison holiday rentals

1. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

2. Direct waterfront renovated cottage.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

4. The gardners Cottage 1 mile from long Island Sound - pet friendly

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

7. Adorable Cottage with Cottage porch, walk to water & town

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

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

10. Historic New England home ,Reunions Beach pass

11. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

12. Walk To Goodspeed Opera House!

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

14. North Fork Resort

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

16. The Stern at Soundview · Beach+Ocean+Sunrise

17. All New Fully Furnished Cozy Studio

18. Keel at Soundview · Beach+OceanView+Sunrise

19. 2BR Apartment Near Wesleyan 301

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

Find holiday rentals that suit your style

Top Madison Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Water's Edge Resort & Spa

Quality Inn

Best Western Executive Hotel Of New Haven - West Haven

Hotel Marcel New Haven, Tapestry Collection By Hilton

New Madison beach house - Ocean front- Great views- booking Summer 2026

Red Roof Inn Meriden

Find out more about Madison

Frequently asked questions

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