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

Madison Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Madison vacation rentals

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
The price is CA $224
CA $517 total
includes taxes & fees
Jul 9 - Jul 10
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (163 reviews)
"Great stay! "
United States
Tanitra
The price is CA $240
CA $341 total
includes taxes & fees
Jul 14 - Jul 15
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
"Great stay & great staff!"
United States
James
The price is CA $487
CA $556 total
includes taxes & fees
Jul 21 - Jul 22
North Fork Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $203
CA $371 total
includes taxes & fees
Jul 13 - Jul 14
1-bedroom cottage with Grove Beach 🏖️ access.

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is CA $236
CA $715 total
includes taxes & fees
Jul 8 - Jul 9
Rogers Lake House (87) · CT College+Beach+USCGA

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is CA $122
CA $275 total
includes taxes & fees
Aug 3 - Aug 4
One bedroom in United States of America, New Haven

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is CA $168
CA $418 total
includes taxes & fees
Jul 8 - Jul 9
All New 1BR with tons of Charm

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is CA $226
CA $430 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Lakefront Tiny House

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town

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, (33 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is CA $214
CA $416 total
includes taxes & fees
Jul 15 - Jul 16
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $214
CA $412 total
includes taxes & fees
Jul 8 - Jul 9
The Stern at Soundview · Beach+Ocean+Sunrise

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is CA $261
CA $539 total
includes taxes & fees
Jul 8 - Jul 9
#24 *Serenity* A Lakefront Cottage Retreat

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is CA $241
CA $403 total
includes taxes & fees
Jul 8 - Jul 9
Walk To Goodspeed Opera House!

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is CA $283
CA $502 total
includes taxes & fees
Jul 13 - Jul 14
Lakefront Boho Tiny House

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is CA $184
CA $308 total
includes taxes & fees
Jul 8 - Jul 9
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Old Lyme
Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (76 reviews)
"Spacious"
United States
Mehul
The price is CA $185
CA $328 total
includes taxes & fees
Jul 19 - Jul 20
Spacious 2 Bedroom apartment close to Yale Bowl

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is CA $168
CA $418 total
includes taxes & fees
Jul 8 - Jul 9
All new 1BR apartment with all the features you are looking for

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is CA $253
CA $510 total
includes taxes & fees
Jul 23 - Jul 24
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
Dwight
8.8 out of 10, Excellent, (3 reviews)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is CA $195
CA $330 total
includes taxes & fees
Jul 19 - Jul 20
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison Hotel Reviews

Find out more about Madison

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Madison?

Yes, we offer vacation rentals in Madison close to RJ Julia Booksellers, or you can go with a more remote 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 vacation home rentals that Madison has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated vacation home rental in Madison is located on the beach and has a balcony, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Madison?

With 33 Expedia vacation rentals, you're sure 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 vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Madison. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.