Search Deals onMadison Vacation Packages
Madison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Price was $1,301, price is now $1,097 per person
$1,097
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Inn By The Sea
Price was $1,763, price is now $1,445 per person
$1,445
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $1,994, price is now $1,693 per person
$1,693
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
The Docent's Collection at 178 Middle Street
Price was $2,062, price is now $1,769 per person
$1,769
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Longfellow Hotel
Price was $1,660, price is now $1,436 per person
$1,436
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
The Nicholson Inn
Price was $1,300, price is now $1,130 per person
$1,130
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Harrington House are located nearby.
We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again..
Reviewed on Oct 9, 2026
Kennebunkport Captains Collection
Price was $1,579, price is now $1,376 per person
$1,376
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
West End Collection at 49 Neal
Price was $1,678, price is now $1,483 per person
$1,483
per person
Dec 26 - Jan 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this inn in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Madison Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Madison Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, just found
$178
Roundtrip
just found
Thu, Nov 26 - Tue, Dec 8
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$185 Roundtrip, found 3 hours ago
$185
Roundtrip
found 3 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Thu, Dec 3 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 16 hours ago
$207
Roundtrip
found 16 hours ago
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