Madison Vacation Packages
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- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
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Your Madison Vacation
Reserve a Madison vacation package that includes everything you need and no unnecessary extras. Great for walking, hiking and views, think about basing yourself in the neighborhood of Essex Village. Hammonasset Beach State Park, Hammonasset Beach and Meigs Point Nature Center are just a few of the many sights worth checking out during your trip to Madison. That dream Madison vacation is a few clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored just for you.
Top Madison Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $1,074, price is now CA $753 per person
CA $753
per person
May 27 - Jun 1
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!
Reviewed on Apr 10, 2026
Madison Hotel Deals
Madison Beach Hotel
94 West Wharf Road Madison CT
Fully refundableReserve now, pay when you stay
The price is CA $392 per night from Apr 26 to Apr 27
CA $392
CA $451 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (362 reviews)
Our room was emasculate, beautiful view and A+ staff!
Reviewed on Apr 15, 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 3 to May 4
CA $163
CA $188 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,087 reviews)
Nice stay, well located and near campus.
Reviewed on Apr 19, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from May 3 to May 4
CA $137
CA $158 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (1,266 reviews)
The staff was so helpful and friendly. The facility was very clean and the price was good.
Reviewed on Apr 17, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
