Search Deals onMadison Vacation Packages
Madison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bourne's Ocean Acres Ogunquit
Price was $732, price is now $586 per person
$586
per person
Aug 20 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this motel 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 Marginal Way are located nearby.
Good location, friendly staff, clean riom
Reviewed on Jul 2, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $1,384, price is now $919 per person
$919
per person
Aug 20 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Ogunquit Playhouse are located nearby.
Très propre, personnel gentille
Reviewed on Jul 1, 2026
Ogunquit River Inn & Suites
Save 100% on your flight
Price was $1,536, price is now $1,051 per person
$1,051
per person
Aug 24 - Aug 30
found 8 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 Footbridge Beach are located nearby.
Everything was good!
Reviewed on Jul 2, 2026
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $1,413, price is now $1,023 per person
$1,023
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Inn at Diamond Cove
Price was $1,434, price is now $1,090 per person
$1,090
per person
Sep 13 - Sep 18
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.
Reviewed on Jun 29, 2026
The Docent's Collection at 121 Middle Street
Price was $1,845, price is now $1,415 per person
$1,415
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
Great spacious place, modern, clean
Reviewed on Jul 2, 2026
Holiday Inn Express Hotel & Suites White River Junction by IHG
Price was $1,029, price is now $803 per person
$803
per person
Aug 1 - Aug 8
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and King Arthur Baking Company are located nearby.
I always find my stays at Holiday Inns to be enjoyable. Staff was very nice. Breakfast was good. Room was large and comfortable. Conveniently located.
Reviewed on Jun 26, 2026
Saco Bay Hotel
Price was $1,020, price is now $813 per person
$813
per person
Aug 14 - Aug 18
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Saco. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Orchard Beach and Saco Museum are located nearby.
Clean and well maintained
Reviewed on Jul 1, 2026
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.
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$165 Roundtrip, found 11 hours ago
$165
Roundtrip
found 11 hours ago
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$196 Roundtrip, found 8 hours ago
$196
Roundtrip
found 8 hours ago
Sat, Aug 29 - Sun, Aug 30
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Mon, Aug 10 - Sat, Aug 22
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$210 Roundtrip, found 20 hours ago
$210
Roundtrip
found 20 hours ago
Discover Other Travel Deals
- Lake Winnipesaukee Vacations
- Story Land Vacations
- White Mountain National Forest Vacations
- Cranmore Mountain Resort Vacations
- Settlers' Green Outlet Village Vacations
- Conway Scenic Railway Vacations
- Squam Lake Vacations
- Saco River Vacations
- Attitash Mountain Resort Vacations
- Waterville Valley Resort Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
