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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.
La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

3 out of 5
Price was $571, price is now $481 per person
$481
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Winston-Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hanes Mall and Adventure Landing Winston-Salem are located nearby.

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,000, price is now $801 per person
$801
per person
Oct 1 - Oct 4
just found
Roundtrip flight included
Dallas (DFW) 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.
From start to finish, I had the most amazing stay at this hotel! The restaurant is delicious and the service in both the restaurant and the hotel is top-notch. The pool and amenities are very delightful and there are free bicycles for loan to ride around on the Greenway nearby. Cannot wait to come back.

Reviewed on Jul 21, 2026

Julian Price House

Julian Price House

3 out of 5
Price was $810, price is now $660 per person
$660
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
We stayed 1 night while in Greensboro and our stay at the Julian Price House could not have been better. What a gorgeous property!

Reviewed on Jul 20, 2026

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

4.5 out of 5
Price was $1,498, price is now $1,250 per person
$1,250
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Book a stay at this luxury vacation home in Winston-Salem. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hanes Mall and Joe White Tennis Center at Hanes Park are located nearby.
Loved this little house and all the attention to detail! Would definitely return.

Reviewed on Jun 17, 2026

Grandover Resort & Spa, a Wyndham Grand Hotel

Grandover Resort & Spa, a Wyndham Grand Hotel

4 out of 5
Price was $954, price is now $807 per person
$807
per person
Oct 1 - Oct 4
just found
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Book a stay at this spa resort in Greensboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wet 'n Wild Emerald Pointe Water Park and First Horizon Coliseum are located nearby.
Staff needs more training

Reviewed on Jul 20, 2026

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $652, price is now $560 per person
$560
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Stay at this B&B in Greensboro. Enjoy free breakfast, free parking, and 5 meeting rooms. Popular attractions First Horizon Coliseum and Wet 'n Wild Emerald Pointe Water Park are located nearby.

Rocky Mount Motel near Hwy 220

Rocky Mount Motel near Hwy 220

2.5 out of 5
Price was $585, price is now $511 per person
$511
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Greensboro (GSO)
Stay at this motel in Rocky Mount. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Harvester Performance Center is located nearby.
Fantastic service, excellently decorated room. Don't let the exterior fool you, superb & clean facility!

Reviewed on Jun 19, 2026

La Quinta Inn & Suites by Wyndham Greensboro NC

La Quinta Inn & Suites by Wyndham Greensboro NC

3 out of 5
Price was $724, price is now $643 per person
$643
per person
Oct 1 - Oct 4
just found
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 in our reviews. Popular attractions First Horizon Coliseum and Wet 'n Wild Emerald Pointe Water Park are located nearby.

Madison Vacation Packages 3-4 Night Stays

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

Proximity Hotel

4 out of 5
Price was $1,000, price is now $801 per person
$801
per person
Oct 1 - Oct 4
just found
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $984, price is now $808 per person
$808
per person
Oct 2 - Oct 5
just found
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

4.5 out of 5
Price was $1,498, price is now $1,250 per person
$1,250
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Grandover Resort & Spa, a Wyndham Grand Hotel

Grandover Resort & Spa, a Wyndham Grand Hotel

4 out of 5
Sedgefield
Price was $954, price is now $807 per person
$807
per person
Oct 1 - Oct 4
just found
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 $672, price is now $588 per person
$588
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Save 100% on your flight
Price was $1,380, price is now $941 per person
$941
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,285, price is now $1,127 per person
$1,127
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Hotel Denim

Hotel Denim

3.5 out of 5
Price was $840, price is now $746 per person
$746
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Aug 18 from Logan Intl. to Piedmont Triad Intl., returning Tue, Aug 25, priced at $228 found 2 days ago
Bargain Flight
Tue, Aug 4 - Tue, Aug 11
PHL
Philadelphia Intl.
GSO
Piedmont Triad Intl.
$244 Roundtrip, found 20 hours ago
$244
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Tue, Aug 4 from Philadelphia Intl. to Piedmont Triad Intl., returning Tue, Aug 11, priced at $244 found 20 hours ago
United
Wed, Aug 19 - Wed, Aug 26
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 19 from Newark Liberty Intl. Airport to Piedmont Triad Intl., returning Wed, Aug 26, priced at $255 found 1 day ago
American Airlines
Sat, Aug 29 - Sat, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$271 Roundtrip, found 16 hours ago
$271
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, Aug 29 from Fort Lauderdale - Hollywood Intl. to Piedmont Triad Intl., returning Sat, Sep 12, priced at $271 found 16 hours ago