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Madison flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,050, price is now $829 per person
$829
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $8,657, price is now $5,611 per person
$5,611
per person
Oct 24 - Oct 29
found 2 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Enjoy the sauna and perks like free self parking.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,173, price is now $1,484 per person
$1,484
per person
Oct 24 - Oct 29
found 2 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,709, price is now $1,298 per person
$1,298
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,065, price is now $837 per person
$837
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Top Madison hotels deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
$484 nightly
The price is $556 total per night
$556 total
Sep 2 - Sep 3
Total with taxes and fees
This hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$72 nightly
The price is $83 total per night
$83 total
Sep 3 - Sep 4
Total with taxes and fees
A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$104 nightly
The price is $120 total per night
$120 total
Aug 25 - Aug 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$365 nightly
The price is $417 total per night
$417 total
Sep 2 - Sep 3
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
$108 nightly
The price is $124 total per night
$124 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $137 total per night
$137 total
Aug 9 - Aug 10
Total with taxes and fees
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
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See all available properties in Madison
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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.

Stay near popular Madison attractions

A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Hammonasset Beach State Park

8.8/10 (137 reviews)
You can take time to visit Hammonasset Beach State Park during your travels to Madison. While you're in the area, stroll along the beautiful beaches.
See properties

Frequently asked questions

How much are vacation packages to Madison?
Travelocity provides flight and hotel vacation packages starting as low as $829. With such amazing bargains, you'll be exploring all of Madison in no time.
How long should my Madison vacation be?
Around 2 nights is the average amount of time travelers vacation in Madison. But how long is right for you all depends on how many magical memories you want to create. Why not stay a couple of extra days and discover some hidden treasures?
Where can I get the best vacation package deals for Madison?
Picking up the perfect package deal to Madison couldn't be easier with Travelocity. With around 400 partner airlines and 1,000,000 properties worldwide, you're flush with choice when it comes to picking your flights and hotels.
Why should I book my Madison vacation bundle via Travelocity?
From our 24/7 customer support to our range of amazing destinations, we're committed to giving you the vacation of a lifetime. All you'll have to do is to click and book — our Price Match Guarantee will make sure you lock in the best price.
Can I save on my Madison car rental if I combine it with my hotel or flight?
With a Madison vacation package, you can bundle your hotel, car and flight bookings and save loads. If you'd love to discover the best of this impressive location, why not make a beeline for Times Square? This renowned attraction is 85 mi from Madison. With a rental car, you'll be there in a flash.
Which airport is best for Madison?
Bradley Intl. Airport (BDL) is one of the top airports for Madison. You'll find it 45 mi north of the buzzing city center. Your other choices are MacArthur Airport (ISP) (45 mi away from central Madison) and Tweed - New Haven Regional Airport (HVN) (17 mi away from central Madison).
What is there to do in Madison?
While veering off the tourist trail is rewarding, you really shouldn't miss the popular attractions that make a place famous. Hammonasset Beach State Park and Hammonasset Beach are just two of them in Madison.
Where should I stay when visiting Madison?
If you're searching for someplace comfortable to base yourself, consider the The Homestead. It's the top pick for many travelers.

Photos of local treasures

Browse Madison vacation photos for more inspiration

A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.
A calm lake at sunset with several sailboats anchored near the shore.
View of a stone jetty stretches into the tranquil ocean under a pastel sky brushed with pink and blue hues, captured from the sandy shore, Madison, Connecticut, United States.
A beach with boats, a sandy shore, and houses in the background.
A house surrounded by autumn-colored trees and a calm lake.

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