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

Madison Vacation Rentals

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Our top choices for Madison vacation rentals

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
$285 nightly
The price is $308
Jun 23 - Jun 24
Total with taxes and fees
1 Min to I-91 - Newly Renovated Modern 2 BR Home

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (157 reviews)
"Great stay! "
United States
Tanitra
$184 nightly
The price is $211
Jun 25 - Jun 26
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (23 reviews)
"Great stay & great staff!"
United States
James
$352 nightly
The price is $402
Jun 23 - Jun 24
Total with taxes and fees
North Fork Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (45 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
$220 nightly
The price is $249
Jun 26 - Jun 27
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (258 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
$287 nightly
The price is $328
Jun 23 - Jun 24
Total with taxes and fees
Cliffside Resort Condominiums

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
$375 nightly
The price is $406
Jun 29 - Jun 30
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$243 nightly
The price is $275
Jun 21 - Jun 22
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
2BR Apartment Near Wesleyan 301

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
$276 nightly
The price is $313
Jun 21 - Jun 22
Total with taxes and fees
Walk To Goodspeed Opera House!

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
$223 nightly
The price is $252
Jun 22 - Jun 23
Total with taxes and fees
Spacious Bohemian Nook

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)
"We had a very nice stay at Roger’s Lake! The house was so cool! It had all the amenities we needed and the location was charming and peaceful. In particular, the beds are really comfortable! They have this awesome exercise room where you can stretch out and enjoy the light. The host, Peter, was especially easy to work with and was very communicative. My family and I are hoping to come back soon for another stay."
United States
Andrea
$417 nightly
The price is $472
Jun 23 - Jun 24
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

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, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$274 nightly
The price is $311
Jun 22 - Jun 23
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

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, (74 reviews)
"Spacious"
United States
Mehul
$204 nightly
The price is $231
Jun 22 - Jun 23
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl

Beautiful Downtown New Haven Retreat

Beautiful Downtown New Haven Retreat
Downtown New Haven
$278 nightly
The price is $316
Jun 21 - Jun 22
Total with taxes and fees
Beautiful Downtown New Haven Retreat

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
$509 nightly
The price is $551
Jun 24 - Jun 25
Total with taxes and fees
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$247 nightly
The price is $280
Jun 23 - Jun 24
Total with taxes and fees
Lakefront Boho Tiny House

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.
$324 nightly
The price is $366
Jul 14 - Jul 15
Total with taxes and fees
Cozy Lakefront Tiny House

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
$626 nightly
The price is $708
Jun 23 - Jun 24
Total with taxes and fees
Beach Cottage, private beach and pass

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

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
$277 nightly
The price is $295
Jun 22 - Jun 23
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation 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 low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $211 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 34 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 North Madison Shopping 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.