Madison Holiday Rentals

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Holiday Rentals in Madison

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
United States
Barb D.
The price is NZ$691
includes taxes & fees
29 Oct - 30 Oct
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is NZ$378
includes taxes & fees
4 Nov - 5 Nov
Cozy Lakefront Tiny House
Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is NZ$401
includes taxes & fees
11 Nov - 12 Nov
Lakefront Boho Tiny House
The Mast at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
United States
Nora M.
The price is NZ$303
includes taxes & fees
19 Nov - 20 Nov
The Mast at Soundview · Beach+Ocean+Sunrise
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is NZ$521
includes taxes & fees
3 Nov - 4 Nov
Cliffside Resort Condominiums
Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
The price is NZ$288
includes taxes & fees
23 Oct - 24 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
The Anchor at Soundview · Beach+Ocean+Sunrise
2.0 star property
8.0 out of 10, Very good, (2)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is NZ$285
includes taxes & fees
23 Oct - 24 Oct
The Anchor at Soundview · Beach+Ocean+Sunrise
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (9)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is NZ$346
includes taxes & fees
23 Oct - 24 Oct
Charming Studio| Near Yale| Downtown New Haven
Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is NZ$463
includes taxes & fees
3 Nov - 4 Nov
Soothing 2-bedroom lower-level apartment in Berlin
Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (16)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is NZ$357
includes taxes & fees
3 Nov - 4 Nov
Family Stays: Middletown, CT
Spacious 2 Bedroom apartment close to Yale Bowl
9.6 out of 10, Exceptional, (67)
"Beautiful space. Everything perfect. "
United States
Mark Z.
The price is NZ$402
includes taxes & fees
26 Oct - 27 Oct
Spacious 2 Bedroom apartment close to Yale Bowl
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is NZ$306
includes taxes & fees
4 Nov - 5 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
The East Rock 4BR Parking Washer & Dryer Walk to Yale
10.0 out of 10, Exceptional, (5)
"We loved everything about our stay. The hosts were wonderful to work with and their home and the surrounding area are absolutely beautiful."
United States
Deanna K.
The price is NZ$573
includes taxes & fees
29 Oct - 30 Oct
The East Rock 4BR Parking Washer & Dryer Walk to Yale
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is NZ$643
includes taxes & fees
27 Oct - 28 Oct
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (75)
"Very nice cabins "
United States
Jairo
The price is NZ$379
includes taxes & fees
27 Oct - 28 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
9.0 out of 10, Wonderful, (10)
"Great 4 day visit to New Haven. We enjoyed the neighborhood and proximity to Yale."
United States
Todd L.
The price is NZ$571
includes taxes & fees
3 Nov - 4 Nov
Sunshine Central | Yale | 3BR | Prking | Wshr/Dryr
Insta-worthy Couples Retreat: Perfect for romantic getaway!
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is NZ$433
includes taxes & fees
29 Oct - 30 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$304
includes taxes & fees
28 Oct - 29 Oct
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
8.0 out of 10, Very good, (1)
"Outstanding location and room. Please recheck the structure of the outdoor stairs. There are no support pullers from the top landing to the ground level. They’re attached directly to the home but has gaps by the windows. The stares are very slippery when wet and the arm rails are below waist level. Unfinished wood rails make splinters a thing. Super clean, quiet and relaxing. Would reserve again if we come back to the area. Thank you so much for all the support. "
United States
Pat D.
The price is NZ$225
includes taxes & fees
23 Oct - 24 Oct
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (5)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is NZ$585
includes taxes & fees
26 Oct - 27 Oct
Angelica’s safe haven @ west haven
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

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$288 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?

Waterfront Estate Home - Beach and Shared Pool - East: This highly rated holiday home rental in Madison is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Madison?

With 33 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?

Family-friendly attractions include RJ Julia Booksellers and Anna Mia's, whereas Hammonasset Beach and Meigs Point Nature Center are a couple of great spots to enjoy the outdoors. Hammonasset Beach State Park and North Madison Shopping 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.