COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Check restrictions for your trip.Opens in new tab or window

Book Exclusive Madison Vacation Packages

Choose one or more items to build your trip:

Madison flight + hotel packages

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
$386

$336

per person
May 10 - May 12
Roundtrip non-stop flight included
Pittsburgh (PIT) to New Haven (HVN)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour fitness center. Traveling on business? Take advantage of the 13 conference rooms, as well as the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.…

Extended Stay America - Shelton - Fairfield County

Extended Stay America - Shelton - Fairfield County

2.5 out of 5
$278

$258

per person
May 10 - May 12
Roundtrip non-stop flight included
Pittsburgh (PIT) to New Haven (HVN)

Free WiFi in public areas, a picnic area, and a safe deposit box are available at this hotel. The front desk is staffed around-the-clock and laundry facilities are on offer.…

Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
$305

$286

per person
May 10 - May 12
Roundtrip non-stop flight included
Pittsburgh (PIT) to New Haven (HVN)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the fitness center and perks like free self parking.…

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
$298

$292

per person
May 10 - May 12
Roundtrip non-stop flight included
Pittsburgh (PIT) to New Haven (HVN)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 8 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour fitness center and perks like free self parking and a free area shuttle.…

Holiday Inn Bridgeport-Trumbull-Fairfield

Holiday Inn Bridgeport-Trumbull-Fairfield

3 out of 5
$306

$305

per person
May 10 - May 12
Roundtrip non-stop flight included
Pittsburgh (PIT) to New Haven (HVN)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, dry cleaning, and luggage storage are also offered.…

Top Madison hotels deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road, Madison, CT
Free Cancellation
Reserve now, pay when you stay
The price is $214 per night
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
The Scranton Seahorse Inn

The Scranton Seahorse Inn

3 out of 5
818 Boston Post Road, Madison, CT
The price is $144 per night
This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Free full breakfast is served. A terrace, a garden, and a ...
Tidewater Inn

Tidewater Inn

3 out of 5
949 Boston Post Road, Madison, CT
The price is $150 per night
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, dry cleaning, and laundry facilities are also on ...
The Homestead

The Homestead

3 out of 5
391 Boston Post Rd, Madison, CT
The price is $200 per night
This bed & breakfast features free WiFi in public areas, wedding services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, ...
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

Madison, CT
Get Rates
This vacation home includes a garden and barbecue grills.
Newly Renovated Near Downtown & Hammonasett Beach

Newly Renovated Near Downtown & Hammonasett Beach

Madison, CT
Get Rates
A garden is available at this vacation home.
Don't see what you're looking for?
See all available properties in Madison
View all properties
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.

Popular places to visit in Madison

Image for Hammonasset Beach State Park

Hammonasset Beach State Park

Explore the great outdoors at Hammonasset Beach State Park, a lovely green space in Madison. While you're in the area, stroll along the beautiful beaches.

Hammonasset Beach State Park
Image for Hammonasset Beach

Hammonasset Beach

Why not spend a lazy afternoon at Hammonasset Beach during your trip to Madison? While you're in the area, stroll along the beaches.

Hammonasset Beach
Image for Yale University

Yale University

Enjoy the collegiate vibe around Yale University, a top college in New Haven. Stroll along the beaches or experience the area's art scene.

Yale University

Frequently asked questions

How much are vacation packages to Madison?
Enjoy a fulfilling travel experience in Madison with a vacation package starting from just $258. Reserving hotels, flights and tours through Travelocity is so simple. What’s more, our deals will leave you with extra money for fun, fun, fun!
Where can I get the best vacation package deals for Madison?
Head straight to Travelocity. With access to 400 airlines and 665,000 properties worldwide, finding the best Madison package deal couldn’t be simpler.
Why should I purchase my Madison vacation bundle with Travelocity?
Because you’ll never wander on your own if you secure your trip through us, and we offer 24/7 customer support and high-quality service to boot. Add to that our Price Match Guarantee and countless experiences to select from. It’s our job to help you have the trip of a lifetime.
Can I save money on my Madison car rental if I combine it with a hotel or flight?
Booking a Madison vacation package with Travelocity is a simple way to save you time and money. You can bundle a car, hotel and flight, or any combination of them, and score awesome discounts. You can also add in some tours and experiences. Once you’ve picked up the keys to your rental car, head out of the neighborhood and discover what the surrounding area has to offer. About 81 mi from Madison, Times Square is the perfect road trip.
What is the best time of year to go to Madison?
If you prefer to wander wisely, January is a terrific time to do it. That’s when hotel rates are at their cheapest. By way of comparison, prices are highest around June. July, August, June are the most popular months to stay in Madison, so expect long lines for major attractions. Hoping to avoid the busy season? You’ll find fewer visitors during December, January, February.
What is there to do in Madison?
Dig out your travel plan and add in Hammonasset Beach State Park and Anna Mias. They’re just two of the top attractions in Madison.
Where should I stay when visiting Madison?
After a fun-filled day of sightseeing around Madison, catch some Zs at the Tidewater Inn. This top option has everything you need for a comfortable stay.

^Savings based on all package bookings with Flight + Hotel made on Travelocity.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.