Madison Holiday Rentals from €205: Search Short-Term Rentals

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Our top choices for Madison holiday rentals

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

Madison

Samantha D.

includes taxes & fees

3 Sept - 4 Sept

1 bedroom, desk, iron/ironing board, travel cot

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

Clinton

JM B.

includes taxes & fees

28 Sept - 29 Sept

Coffee/tea maker, fridge, microwave, oven

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

Clinton

Wink V.

includes taxes & fees

1 Sept - 2 Sept

4. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Morainny

includes taxes & fees

7 Sept - 8 Sept

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

Westbrook Center

"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."

Sandra Hart

includes taxes & fees

9 Sept - 10 Sept

6. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

Clinton

Elizabeth C.

includes taxes & fees

28 Sept - 29 Sept

7. Historic New England home ,Reunions Beach pass

Guilford

Liz H.

includes taxes & fees

14 Sept - 15 Sept

Smart TV, fireplace, books, music library

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

Haddam

Kate F.

includes taxes & fees

29 Sept - 30 Sept

9. Walk To Goodspeed Opera House!

East Haddam

Amber J.

includes taxes & fees

31 Aug - 1 Sept

10. North Fork Resort

Greenport

Lisa

includes taxes & fees

7 Sept - 8 Sept

11. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Westbrook Center

Kate G.

12. All New 1BR with tons of Charm

Wallingford Center

ALRUNDUS L.

includes taxes & fees

31 Aug - 1 Sept

1 bedroom, iron/ironing board, WiFi, bed sheets

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

Wallingford Center

Jeanette W.

includes taxes & fees

31 Aug - 1 Sept

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

Saybrook Manor

Alexis L.

includes taxes & fees

30 Sept - 1 Oct

15. All New Studio apartment in center of town

Wallingford Center

Nadine C.

includes taxes & fees

31 Aug - 1 Sept

16. Cliffside Resort Condominiums

Greenport

Christine

includes taxes & fees

21 Sept - 22 Sept

1 bedroom, desk, iron/ironing board, WiFi

17. One bedroom in United States of America, New Haven

Dwight

Rosanne M.

includes taxes & fees

31 Aug - 1 Sept

18. The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.

Downtown New Haven

"Great little downtown apartment! Small - good for up to two people. Nicely appointed and decorated, great sectional sofa, big TVs where we wanted them. Host was kind and helpful and accommodating. Location is pretty much across State St from the State Street RR Station, a block and a half from the Green, and near everything. Orange Street (half a block away) has a ton of bars and restaurants. We enjoyed our stay!"

George Z.

includes taxes & fees

1 Sept - 2 Sept

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

Old Lyme

Lylian

includes taxes & fees

31 Aug - 1 Sept

20. Keel at Soundview · Beach+OceanView+Sunrise

Old Lyme

Joseph O.

includes taxes & fees

9 Sept - 10 Sept

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Top Madison Hotel Reviews

The Shoals Suites and Slips

10/10 Excellent

"Loved everything about our stay!"

Red Roof Inn Meriden

10/10 Excellent

"The room was spotless, and the shower was fantastic, but what I loved most was that we forgot our wall chargers, and they were provided as a room amenity. There’s also a microwave at the entrance. Small details like that make a big difference. We’re also traveling with our dog, Bear, just like many others, and not only did they allow dogs, but they didn’t charge an extra fee. I really appreciate that."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

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, apart-hotels, 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 €205 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.

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 East Wharf Beach Park 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 Meigs Point Nature Center 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. 1-bedroom cottage with Grove Beach 🏖️ access.

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

4. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

6. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

7. Historic New England home ,Reunions Beach pass