Search Deals onMadison Vacation Packages
Madison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Weldon Hotel
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Portland Harbor Hotel
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Docent's Collection
Save 100% on your flight
per person
Sep 29 - Oct 2
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located nearby.
The McKernan Inn
Save 100% on your flight
per person
Sep 29 - Oct 2
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Goose Rocks Beach are located nearby.
Inn By The Sea
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Ogunquit River Inn & Suites
per person
Oct 19 - Oct 25
found 23 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach 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, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Sun, Oct 12 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Tue, Sep 2 - Tue, Sep 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
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