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Madison Vacation Packages

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Madison Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Save 100% on your flight
Price was $709, price is now $502 per person
$502
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,097, price is now $821 per person
$821
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,072, price is now $811 per person
$811
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this 4.5-star 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,257, price is now $996 per person
$996
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $872, price is now $694 per person
$694
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,229, price is now $993 per person
$993
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $957, price is now $791 per person
$791
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this 3-star 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.
Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Price was $1,199, price is now $993 per person
$993
per person
Dec 29 - Jan 2
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 3-star B&B in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.

Madison Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $872, price is now $694 per person
$694
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,097, price is now $821 per person
$821
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $958, price is now $741 per person
$741
per person
Dec 29 - Jan 2
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,257, price is now $996 per person
$996
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Madison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Save 100% on your flight
Price was $709, price is now $502 per person
$502
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $685, price is now $512 per person
$512
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,072, price is now $811 per person
$811
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $980, price is now $768 per person
$768
per person
Nov 25 - Nov 30
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Sat, Nov 8 - Sat, Nov 15
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Nov 8 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 15, priced at $132 found 3 days ago
United
Tue, Nov 11 - Wed, Nov 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Tue, Nov 11 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Nov 12, priced at $137 just found
Delta
Sun, Nov 9 - Wed, Nov 12
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Delta flight, departing Sun, Nov 9 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Nov 12, priced at $150 just found
Delta
Sat, Nov 8 - Thu, Nov 13
LGA
LaGuardia
PWM
Portland Intl. Jetport
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Delta flight, departing Sat, Nov 8 from LaGuardia to Portland Intl. Jetport, returning Thu, Nov 13, priced at $150 just found