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Jamestown Vacation Packages

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Jamestown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $568, price is now $490 per person
$490
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Very friendly and helpful staff. The room was clean and the beds very comfortable.

Reviewed on Aug 20, 2026

Julian Price House

Julian Price House

3 out of 5
Price was $920, price is now $656 per person
$656
per person
Oct 1 - Oct 4
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.
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

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

4.5 out of 5
Price was $1,294, price is now $1,074 per person
$1,074
per person
Oct 3 - Oct 6
found 20 hours 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

Hampton Inn Asheboro

Hampton Inn Asheboro

2.5 out of 5
Price was $751, price is now $636 per person
$636
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
Book a stay at this business-friendly hotel in Asheboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions North Carolina Zoo and Cinemark Asheboro are located nearby.

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $627, price is now $539 per person
$539
per person
Oct 1 - Oct 4
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.

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $980, price is now $846 per person
$846
per person
Oct 1 - Oct 4
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 Greensboro Aquatic Center are located nearby.
Lovely stay and everyone was kind and helpful! Food was also amazing!

Reviewed on Aug 20, 2026

Pandora's Manor Bed & Breakfast

Pandora's Manor Bed & Breakfast

3.5 out of 5
Price was $1,294, price is now $1,135 per person
$1,135
per person
Oct 29 - Nov 1
found 1 day 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.
Exceptionally beautiful property and exceptional customer service. Graciously accommodated a change in plans, excellent communication throughout, friendly welcome and went the extra mile in all ways to make our very quick trip memorable!

Reviewed on Feb 20, 2026

Red Roof Inn Greensboro Coliseum

Red Roof Inn Greensboro Coliseum

2 out of 5
Price was $741, price is now $657 per person
$657
per person
Oct 29 - Nov 1
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 a 24-hour front desk. Popular attractions Greensboro Aquatic Center and First Horizon Coliseum are located nearby.
. Kids running around all night no staff after a certain time so you have no one to speak to. Banging on the walls all night

Reviewed on Aug 16, 2026

Jamestown Vacation Packages 3-4 Night Stays

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

Hotel Denim

3.5 out of 5
Price was $627, price is now $539 per person
$539
per person
Oct 1 - Oct 4
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 $920, price is now $656 per person
$656
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

4.5 out of 5
Price was $1,294, price is now $1,074 per person
$1,074
per person
Oct 3 - Oct 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
Hampton Inn Asheboro

Hampton Inn Asheboro

2.5 out of 5
Price was $751, price is now $636 per person
$636
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)

Jamestown Vacation Packages 5-7 Night Stays

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

Hotel Denim

3.5 out of 5
Price was $869, price is now $680 per person
$680
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Greensboro (GSO)
Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
Price was $993, price is now $825 per person
$825
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Greensboro (GSO)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,388, price is now $1,159 per person
$1,159
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Greensboro (GSO)
The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $1,318, price is now $1,178 per person
$1,178
per person
Oct 7 - Oct 12
found 7 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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, Aug 22 - Sun, Aug 23
BOS
Logan Intl.
GSO
Piedmont Triad Intl.
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Sat, Aug 22 from Logan Intl. to Piedmont Triad Intl., returning Sun, Aug 23, priced at $251 found 1 hour ago
United
Thu, Oct 29 - Sun, Nov 1
EWR
Newark Liberty Intl. Airport
GSO
Piedmont Triad Intl.
$269 Roundtrip, found 21 hours ago
$269
Roundtrip
found 21 hours 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 21 hours ago
Delta
Wed, Nov 25 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
GSO
Piedmont Triad Intl.
$275 Roundtrip, found 5 days ago
$275
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Nov 25 from Fort Lauderdale - Hollywood Intl. to Piedmont Triad Intl., returning Tue, Dec 1, priced at $275 found 5 days ago
Bargain Flight
Tue, Oct 27 - Sat, Nov 7
LAX
Los Angeles Intl.
GSO
Piedmont Triad Intl.
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Oct 27 from Los Angeles Intl. to Piedmont Triad Intl., returning Sat, Nov 7, priced at $292 found 2 days ago