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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.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $920, price is now $723 per person
$723
per person
Jun 12 - Jun 14
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Maine Mall are located nearby.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,325, price is now $859 per person
$859
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,361, price is now $962 per person
$962
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southport Memorial Library and Hendricks Hill Museum are located nearby.
Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Price was $1,223, price is now $910 per person
$910
per person
May 29 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
Book a stay at this spa hotel in Whitefield. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Santa's Village and Weathervane Theatre are located nearby.
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Save 100% on your flight
Price was $2,451, price is now $1,830 per person
$1,830
per person
Jul 9 - Jul 16
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,002, price is now $1,511 per person
$1,511
per person
Jul 13 - Jul 17
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this 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.
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Save 100% on your flight
Price was $1,562, price is now $1,204 per person
$1,204
per person
Jul 9 - Jul 16
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Sunset Hill House

Sunset Hill House

4 out of 5
Price was $960, price is now $751 per person
$751
per person
May 29 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
Book a stay at this golf hotel in Sugar Hill. Enjoy free parking, a golf course, and daily housekeeping. Popular attractions Franconia Notch State Park and Sunset Hill Golf Course 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
Save 100% on your flight
Price was $1,618, price is now $1,178 per person
$1,178
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,942, price is now $1,448 per person
$1,448
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,002, price is now $1,511 per person
$1,511
per person
Jul 13 - Jul 17
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,611, price is now $1,216 per person
$1,216
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)

Madison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,325, price is now $859 per person
$859
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,991, price is now $2,091 per person
$2,091
per person
Jul 9 - Jul 16
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,361, price is now $962 per person
$962
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Price was $1,223, price is now $910 per person
$910
per person
May 29 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)

Top Flight Deals

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

JetBlue Airways
Sat, May 9 - Thu, May 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, May 9 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, May 21, priced at $161 found 4 days ago
United
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$161 Roundtrip, found 3 hours ago
$161
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Jun 17, priced at $161 found 3 hours ago
Delta
Sun, May 17 - Sat, May 23
LGA
LaGuardia
PWM
Portland Intl. Jetport
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 17 from LaGuardia to Portland Intl. Jetport, returning Sat, May 23, priced at $161 found 5 days ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 2 days ago