Search Deals on
Madison Vacation Packages

Build your package with 2 more options

Madison Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
Price was $462, price is now $408 per person
$408
per person
Sep 18 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Greensboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions All-A-Flutter Butterfly Farm and Piedmont Triad Farmers Market are located nearby.
Friendly, helpful staff, Nice, clean hotel, Room clean for the most part-a few spider webs by the windows.

Reviewed on Aug 11, 2026

Julian Price House

Julian Price House

3 out of 5
Price was $1,254, price is now $911 per person
$911
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Book a stay at this golf guesthouse in Greensboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions First Horizon Coliseum and Wet 'n Wild Emerald Pointe Water Park are located nearby.
The Julian Price House is amazing and surprising place to stay in the heart of Greensboro. It felt like being in another world.

Reviewed on Aug 12, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $681, price is now $576 per person
$576
per person
Sep 18 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Greensboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions First Horizon Coliseum and Wet 'n Wild Emerald Pointe Water Park are located nearby.

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $650, price is now $555 per person
$555
per person
Sep 18 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Greensboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions First Horizon Coliseum and Wet 'n Wild Emerald Pointe Water Park are located nearby.

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $502, price is now $436 per person
$436
per person
Sep 18 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Stay at this hotel in Greensboro. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions First Horizon Coliseum and The Bog Garden are located nearby.

Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
Price was $474, price is now $420 per person
$420
per person
Sep 18 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Greensboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Greensboro Aquatic Center and First Horizon Coliseum are located nearby.
Wonderful Stay ⭐⭐⭐⭐⭐ I had a fantastic stay at this hotel! Everything was clean, comfortable, and welcoming, and the staff went above and beyond to make us feel at home. The service was excellent, the atmosphere was relaxing, and the overall experience exceeded our expectations. I truly enjoyed our time here and would happily come back again. Highly recommended for anyone looking for a great place to stay! ⭐⭐⭐⭐⭐

Reviewed on Aug 12, 2026

Country Inn & Suites by Radisson, Greensboro, NC

Country Inn & Suites by Radisson, Greensboro, NC

2.5 out of 5
Price was $1,041, price is now $926 per person
$926
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Greensboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greensboro Aquatic Center and First Horizon Coliseum are located nearby.
Was a good experience!!

Reviewed on Aug 9, 2026

Burke Manor Inn & Pavilion

Burke Manor Inn & Pavilion

3.5 out of 5
Price was $664, price is now $592 per person
$592
per person
Sep 18 - Sep 20
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Stay at this hotel in Gibsonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gibsonville Garden Railroad and Alumni Gym are located nearby.
Beautiful 100+ year old Bed and Breakfast. The food and hospitality were excellent. We would definitely go back.

Reviewed on Jun 22, 2026

Madison Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
Price was $506, price is now $445 per person
$445
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $1,254, price is now $911 per person
$911
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Hotel Denim

Hotel Denim

3.5 out of 5
Price was $716, price is now $620 per person
$620
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,057, price is now $931 per person
$931
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)

Madison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
Price was $592, price is now $499 per person
$499
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Greensboro (GSO)
Holiday Inn Express & Suites Winston Salem Sw Clemmons by IHG

Holiday Inn Express & Suites Winston Salem Sw Clemmons by IHG

2.5 out of 5
Price was $941, price is now $780 per person
$780
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Greensboro (GSO)
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $678, price is now $587 per person
$587
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Greensboro (GSO)
Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
Price was $703, price is now $618 per person
$618
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Greensboro (GSO)

Top Flight Deals

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

Bargain Flight
Tue, Aug 18 - Tue, Aug 25
BOS
Logan Intl.
GSO
Piedmont Triad Intl.
$242 Roundtrip, found 5 hours ago
$242
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Aug 18 from Logan Intl. to Piedmont Triad Intl., returning Tue, Aug 25, priced at $242 found 5 hours ago
United
Thu, Oct 29 - Sun, Nov 1
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$269 Roundtrip, found 1 hour ago
$269
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Oct 29 from Newark Liberty Intl. Airport to Piedmont Triad Intl., returning Sun, Nov 1, priced at $269 found 1 hour ago
Bargain Flight
Sat, Sep 12 - Sat, Sep 19
LGA
LaGuardia
GSO
Piedmont Triad Intl.
$279 Roundtrip, found 6 days ago
$279
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sat, Sep 12 from LaGuardia to Piedmont Triad Intl., returning Sat, Sep 19, priced at $279 found 6 days ago
Delta
Sat, Sep 5 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$306 Roundtrip, found 3 days ago
$306
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 5 from Fort Lauderdale - Hollywood Intl. to Piedmont Triad Intl., returning Tue, Sep 8, priced at $306 found 3 days ago