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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.
OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
Price was $673, price is now $594 per person
$594
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
Stay at this hotel in Kernersville. Enjoy free WiFi, free parking, and room service. Popular attractions Kernersville Golf Center and K'ville Indie Flea are located nearby.
Roach motel

Reviewed on Oct 4, 2026

Julian Price House

Julian Price House

3 out of 5
Save 100% on your flight
Price was $1,674, price is now $1,047 per person
$1,047
per person
Jan 2 - Jan 9
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 Latham Park Tennis Center are located nearby.
I wish I could’ve stayed longer. It was very peaceful and comfortable.

Reviewed on Oct 15, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,575, price is now $1,359 per person
$1,359
per person
Nov 24 - Nov 29
found 1 day 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 The Bog Garden are located nearby.
Our room was clean and nice. Friendly staff as well!

Reviewed on Oct 11, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,832, price is now $1,596 per person
$1,596
per person
Nov 24 - Nov 29
found 1 day 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 Regal Greensboro Grande are located nearby.

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $940, price is now $832 per person
$832
per person
Nov 25 - Dec 2
found 1 day 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.
Great customer care

Reviewed on Oct 18, 2026

Comfort Suites Greensboro - High Point

Comfort Suites Greensboro - High Point

2.5 out of 5
Price was $908, price is now $811 per person
$811
per person
Jan 2 - Jan 9
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 All-A-Flutter Butterfly Farm and Piedmont Triad Farmers Market are located nearby.

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $839, price is now $756 per person
$756
per person
Jan 2 - Jan 9
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Greensboro (GSO)
Stay at this hotel in Winston-Salem. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hanes Mall and Old Salem are located nearby.

Pandora's Manor Bed & Breakfast

Pandora's Manor Bed & Breakfast

3.5 out of 5
Price was $1,999, price is now $1,804 per person
$1,804
per person
Dec 18 - Dec 23
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Stay at this B&B in High Point. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Market Square and Centennial Station Arts Center are located nearby.
Absolutely wonderful. Don't tell anyone.

Reviewed on Aug 27, 2026

Madison Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

3 out of 5
Price was $785, price is now $727 per person
$727
per person
Dec 23 - Dec 27
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $1,599, price is now $1,280 per person
$1,280
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,560, price is now $1,411 per person
$1,411
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Grandover Resort & Spa, a Wyndham Grand Hotel

Grandover Resort & Spa, a Wyndham Grand Hotel

4 out of 5
Sedgefield
Price was $1,377, price is now $1,279 per person
$1,279
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)

Madison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

3 out of 5
Price was $879, price is now $774 per person
$774
per person
Nov 25 - Dec 2
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
Save 100% on your flight
Price was $1,674, price is now $1,047 per person
$1,047
per person
Jan 2 - Jan 9
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Greensboro (GSO)
Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,575, price is now $1,359 per person
$1,359
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,832, price is now $1,596 per person
$1,596
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)

Top Flight Deals

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

Bargain Flight
Sat, Oct 31 - Tue, Nov 3
BOS
Logan Intl.
GSO
Piedmont Triad Intl.
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Oct 31 from Logan Intl. to Piedmont Triad Intl., returning Tue, Nov 3, priced at $248 found 1 day ago
Bargain Flight
Wed, Nov 25 - Tue, Dec 1
PHL
Philadelphia Intl.
GSO
Piedmont Triad Intl.
$277 Roundtrip, found 4 hours ago
$277
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Wed, Nov 25 from Philadelphia Intl. to Piedmont Triad Intl., returning Tue, Dec 1, priced at $277 found 4 hours ago
United
Tue, Dec 8 - Mon, Dec 14
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$319 Roundtrip, found 9 hours ago
$319
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Dec 8 from Newark Liberty Intl. Airport to Piedmont Triad Intl., returning Mon, Dec 14, priced at $319 found 9 hours ago
American Airlines
Wed, Nov 25 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$321 Roundtrip, just found
$321
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 25 from Fort Lauderdale - Hollywood Intl. to Piedmont Triad Intl., returning Tue, Dec 1, priced at $321 just found