Search Deals onMadison Vacation Packages
Madison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Winston-Salem
Price was $452, price is now $381 per person
$381
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Staf was friendly and helpful. Room was clean.
Reviewed on Sep 1, 2026
Julian Price House
Price was $1,415, price is now $1,050 per person
$1,050
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 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.
Proximity Hotel
Price was $1,465, price is now $1,115 per person
$1,115
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.
King beds Hot Tub Arcade Luxury Showers
Save 100% on your flight
Price was $2,021, price is now $1,670 per person
$1,670
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this luxury vacation home in Kernersville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Walkertown Community Park and Old Walkertown Stadium are located nearby.
Hotel Denim
Price was $612, price is now $515 per person
$515
per person
Nov 6 - Nov 9
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.
O.Henry Hotel
Price was $807, price is now $681 per person
$681
per person
Nov 21 - Nov 24
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.
It's our third time staying, & the staff remains exemplary. They are the standout and the reason that we will always stay at the o henry. It was wonderful seeing Sherone again. Hannah, Lakiya,& other front desk goddesses are delightful. The tea & jazz staff are fantastic. Kate & Courtney improved our mornings dramatically, & Ashleigh was lovely for our dinner.
Tyler and the other porters are fantastic at their jobs, though it hurt my heart to see them dressed like it was 50 degrees out amidst the brutal heat & humidity. It would be lovely if they could lose the sweater vest and long sleeves and have more suitable summer attire.
The only downside was I had to use my cell as a Hotspot to access wifi for my tablet, my dad's laptop, and our Amazon fire.
Reviewed on Aug 31, 2026
Atrium Inn
Price was $671, price is now $569 per person
$569
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Stay at this hotel in High Point. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Market Square and Centennial Station Arts Center are located nearby.
KingBed PetFriendly Washer Dryer Sleep16
Price was $995, price is now $852 per person
$852
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this luxury vacation home in Kernersville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Walkertown Community Park and Old Walkertown Stadium 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.
Wed, Sep 30 - Sat, Oct 3
LGA
LaGuardia
GSO
Piedmont Triad Intl.
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Wed, Oct 14 - Tue, Oct 20
BOS
Logan Intl.
GSO
Piedmont Triad Intl.
$275 Roundtrip, found 1 day ago
$275
Roundtrip
found 1 day ago
Wed, Nov 25 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Sat, Nov 7 - Mon, Nov 23
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$289 Roundtrip, found 21 hours ago
$289
Roundtrip
found 21 hours ago
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