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

Madison Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is NZ$519
includes taxes & fees
17 Nov - 18 Nov
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
The price is NZ$464
includes taxes & fees
19 Nov - 20 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (32 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is NZ$616
includes taxes & fees
16 Nov - 17 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A cabin with a dining table set for two, a bicycle, and a small porch area.

4. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (223 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is NZ$348
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is NZ$1,039
includes taxes & fees
17 Nov - 18 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
A reception desk with a staff member, a guest, and a child.

6. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Quick overnight stop, rooms clean and everything worked as expected."
United States
Anonymous traveller
The price is NZ$162
includes taxes & fees
1 Dec - 2 Dec
Cozy 1 King Bed | Smoking
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

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
Adorable Cottage with Cottage porch, walk to water & town
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

8. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is NZ$1,091
includes taxes & fees
16 Nov - 17 Nov
Historic New England home ,Reunions Beach pass
A large, white, multi-story building with a prominent tower and a flag on top.

9. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is NZ$413
includes taxes & fees
10 Dec - 11 Dec
Walk To Goodspeed Opera House!
A balcony with a view of the ocean, a lawn, and a house in the background.

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is NZ$598
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is NZ$638
includes taxes & fees
16 Nov - 17 Nov
North Fork Resort
A hotel room with two beds, a desk, and a chair.

12. Spacious 2 Full Beds Nsmk

Spacious 2 Full Beds Nsmk
Branford
10.0 out of 10, Exceptional, (52 reviews)
"Checked in quickly and bed was cozy which really helped after long drive. Shower stall size was just right too."
United States
Anonymous traveller
The price is NZ$162
includes taxes & fees
1 Dec - 2 Dec
Spacious 2 Full Beds Nsmk
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (16 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
The price is NZ$973
includes taxes & fees
17 Nov - 18 Nov
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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.

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

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (40 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is NZ$450
includes taxes & fees
1 Dec - 2 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

15. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
Brand New Platform #1
A hotel reception desk with a staff member, a guest, and a child.

16. MS6 Branford | 1 King Bed Smk, Micfridge

MS6 Branford | 1 King Bed Smk, Micfridge
Branford
10.0 out of 10, Exceptional, (50 reviews)
"Those beds were very large and super cozy!"
United States
Anonymous traveller
The price is NZ$170
includes taxes & fees
1 Dec - 2 Dec
MS6 Branford | 1 King Bed Smk, Micfridge
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

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

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is NZ$995
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

18. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals
Branford
9.4 out of 10, Exceptional, (86 reviews)
"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."
United States
Vincent
The price is NZ$525
includes taxes & fees
16 Nov - 17 Nov
Cozy Home near private beach , close to New Haven area colleges Hospitals
A reception desk with a staff member, a guest, and a child.

19. Cozy 1 King Bed | Non-Smoking

Cozy 1 King Bed | Non-Smoking
Branford
10.0 out of 10, Exceptional, (55 reviews)
"Stayed one night, quick checkout process got me back on road promptly!"
United States
Anonymous traveller
The price is NZ$162
includes taxes & fees
1 Dec - 2 Dec
Cozy 1 King Bed | Non-Smoking
A reception desk with a staff member, a guest, and a child.

20. 1 King Bed | Mob Acc Tub, Nsmk

1 King Bed | Mob Acc Tub, Nsmk
Branford
10.0 out of 10, Exceptional, (51 reviews)
"Quiet evenings with an easy check-in process made this place worth returning to if passing by again soon."
United States
Anonymous traveller
The price is NZ$164
includes taxes & fees
1 Dec - 2 Dec
1 King Bed | Mob Acc Tub, Nsmk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

New Haven Hotel

New Haven Hotel

8/10 Good
"Gym is really warm and has no windows. Room was clean and staff was really nice."
Torie 2-night trip
Posted 3 hours ago
New Haven Hotel

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$348 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 Scranton Memorial Library 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.