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Winston-Salem Vacation Packages

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Winston-Salem Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Fairview Inn Airport

Fairview Inn Airport

2.5 out of 5
Price was $788, price is now $572 per person
$572
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Stay at this motel in Greensboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions All-A-Flutter Butterfly Farm and Piedmont Triad Farmers Market are located nearby.
Great Customer Service and a great hospitality.

Reviewed on Sep 25, 2026

Julian Price House

Julian Price House

3 out of 5
Save 100% on your flight
Price was $1,437, price is now $884 per person
$884
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.

OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
Price was $843, price is now $593 per person
$593
per person
Nov 2 - Nov 5
found 12 hours ago
Roundtrip flight included
New York (LGA) 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.
Kristen at the front was a doll. The room was cozy and clean. It's next to a great little bar. So you don't have to drink and Uber. Or worst, drink and drive. Everything is 20 minutes away from OYO Hotel. Was in town for awedding, just neededa bed and a place to keep my stuff. Recommend, and will come back.

Reviewed on Sep 13, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,205, price is now $867 per person
$867
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.

Wingate by Wyndham High Point/Greensboro/Airport South

Wingate by Wyndham High Point/Greensboro/Airport South

3 out of 5
Price was $842, price is now $606 per person
$606
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Book a stay at this business-friendly hotel in High Point. 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 Regal Palladium are located nearby.

Park View Inn

Park View Inn

2.5 out of 5
Price was $821, price is now $604 per person
$604
per person
Nov 2 - Nov 5
found 10 hours ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Stay at this motel in Greensboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions First Horizon Coliseum and Gillespie Golf Course are located nearby.

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,304, price is now $962 per person
$962
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Beautifully appointed hotel in keeping with the fine tradition of Southern hospitality. Every staff member we encountered was gracious, friendly and helpful. Our king room was spacious and inviting. Even the bathroom was sublime. The hotel bar was buzzing with good cheer on a Friday night. Our evening dinner and service at the on-site Green Valley Grill were excellent. Thanks goes to those who resurrected this newer O.Henry in the spirit and style of the original 1919 downtown landmark. Highly recommend.

Reviewed on Sep 22, 2026

Clarion Pointe

Clarion Pointe

2.5 out of 5
Price was $813, price is now $603 per person
$603
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Book a stay at this business-friendly hotel in High Point. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Kersey Valley Attractions and Kersey Valley Laser Tag are located nearby.
Everyone was very nice and welcoming, and the room was very clean. Overall, we had a pleasant experience and really appreciated the friendly service and cleanliness.

Reviewed on Sep 20, 2026

Winston-Salem Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fairview Inn Airport

Fairview Inn Airport

2.5 out of 5
Price was $788, price is now $572 per person
$572
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Save 100% on your flight
Price was $994, price is now $658 per person
$658
per person
Nov 11 - Nov 15
found 5 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Greensboro (GSO)
OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
Price was $843, price is now $593 per person
$593
per person
Nov 2 - Nov 5
found 12 hours ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
Wingate by Wyndham High Point/Greensboro/Airport South

Wingate by Wyndham High Point/Greensboro/Airport South

3 out of 5
Price was $842, price is now $606 per person
$606
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)

Winston-Salem Vacation Packages 5-7 Night Stays

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

Proximity Hotel

4 out of 5
Price was $1,205, price is now $867 per person
$867
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Greensboro (GSO)
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Save 100% on your flight
Price was $1,437, price is now $884 per person
$884
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Greensboro (GSO)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,304, price is now $962 per person
$962
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Greensboro (GSO)
Pandora's Manor Bed & Breakfast

Pandora's Manor Bed & Breakfast

3.5 out of 5
West High Avenue Historic District
Save 100% on your flight
Price was $1,944, price is now $1,554 per person
$1,554
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Greensboro (GSO)

Top Flight Deals

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

Bargain Flight
Wed, Oct 28 - Tue, Nov 10
BOS
Logan Intl.
GSO
Piedmont Triad Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Oct 28 from Logan Intl. to Piedmont Triad Intl., returning Tue, Nov 10, priced at $237 found 1 day ago
Delta
Wed, Nov 25 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$295 Roundtrip, just found
$295
Roundtrip
just found
Select Delta flight, departing Wed, Nov 25 from Fort Lauderdale - Hollywood Intl. to Piedmont Triad Intl., returning Tue, Dec 1, priced at $295 just found
Bargain Flight
Tue, Nov 10 - Tue, Nov 17
LGA
LaGuardia
GSO
Piedmont Triad Intl.
$295 Roundtrip, found 2 days ago
$295
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Nov 10 from LaGuardia to Piedmont Triad Intl., returning Tue, Nov 17, priced at $295 found 2 days ago
United
Fri, Nov 6 - Mon, Nov 9
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select United flight, departing Fri, Nov 6 from Newark Liberty Intl. Airport to Piedmont Triad Intl., returning Mon, Nov 9, priced at $299 found 1 day ago