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16 Dec - 17 Dec
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17 Dec - 18 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Upshur County hotels

Mini-fridge, microwave
Executive Inn & Suites

Executive Inn & Suites

Executive Inn & Suites
2.5 star property
Pittsburg
7.4 out of 10, Good, (15)
"I had a wonderful stay "
United States
Brian
The price is 1.704.457 ₫
1.926.036 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Executive Inn & Suites
Lobby
Regency Inn & Suites

Regency Inn & Suites

Regency Inn & Suites
2.5 star property
Gladewater
7.4 out of 10, Good, (208)
"I liked that it was close to where we needed to be the next day, clean, and the price wasn't bad. "
United States
Amie
The price is 1.420.315 ₫
1.604.990 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Regency Inn & Suites
Exterior
Oaklea Mansion Bed and Breakfast

Oaklea Mansion Bed and Breakfast

Oaklea Mansion Bed and Breakfast
4.0 star property
Winnsboro
9.6 out of 10, Exceptional, (16)
"A very nice place to stay. Had a very nice host and good breakfast. "
United States
John
The price is 5.445.549 ₫
6.534.660 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Oaklea Mansion Bed and Breakfast
House (1 Bedroom) | Front of property
Winnsboro Tiny House w/ Trails, Yard Games & More!

Winnsboro Tiny House w/ Trails, Yard Games & More!

Winnsboro Tiny House w/ Trails, Yard Games & More!
3.0 star property
Winnsboro
Winnsboro Tiny House w/ Trails, Yard Games & More!
Comfort Room | Bed sheets
Economy Inn

Economy Inn

Economy Inn
2.0 star property
Gladewater
7.0 out of 10, Good, (24)
"It was clean friendly and convenient for everything"
United States
Teisha
The price is 1.420.578 ₫
1.605.253 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Economy Inn
House (3 Bedrooms) | Interior
Winnsboro Home on 17 Acres: Outdoor Spots & Trails

Winnsboro Home on 17 Acres: Outdoor Spots & Trails

Winnsboro Home on 17 Acres: Outdoor Spots & Trails
3.0 star property
Winnsboro
Winnsboro Home on 17 Acres: Outdoor Spots & Trails
House (2 Bedrooms) | Interior
Walk to Water: Lake O' the Pines Cabin

Walk to Water: Lake O' the Pines Cabin

Walk to Water: Lake O' the Pines Cabin
3.0 star property
Ore City
Walk to Water: Lake O' the Pines Cabin
Apartment (1 Bedroom) | Interior
Blue Jay Cottage' - Pittsburg Studio on Winery!

Blue Jay Cottage' - Pittsburg Studio on Winery!

Blue Jay Cottage' - Pittsburg Studio on Winery!
3.0 star property
Pittsburg
The price is 3.631.056 ₫
5.767.327 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Blue Jay Cottage' - Pittsburg Studio on Winery!
TV, DVD player
Lakefront Cabin w/ 2 Lofts, Boats on 4 Acres

Lakefront Cabin w/ 2 Lofts, Boats on 4 Acres

Lakefront Cabin w/ 2 Lofts, Boats on 4 Acres
3.0 star property
Winnsboro
10.0 out of 10, Exceptional, (1)
"The cutest little lake place. It was better than expected. Very clean and had everything we needed and more. Would highly recommend!"
United States
Lynn
Lakefront Cabin w/ 2 Lofts, Boats on 4 Acres
House (1 Bedroom) | Interior
Quiet Lake Gladewater Getaway w/ Dock & Kayaks!

Quiet Lake Gladewater Getaway w/ Dock & Kayaks!

Quiet Lake Gladewater Getaway w/ Dock & Kayaks!
3.0 star property
Gladewater
10.0 out of 10, Exceptional, (1)
"Our stay was great. Unit had everything we needed. It was quiet and situated on the shores of Lake Gladewater with picturesque views of the lake. "
United States
William
Quiet Lake Gladewater Getaway w/ Dock & Kayaks!
Cottage (3 Bedrooms) | Interior
Home On Lake Bob Sandlin w/ Private Boat Dock!

Home On Lake Bob Sandlin w/ Private Boat Dock!

Home On Lake Bob Sandlin w/ Private Boat Dock!
3.0 star property
Pittsburg
Home On Lake Bob Sandlin w/ Private Boat Dock!
House (2 Bedrooms) | Interior
Secluded Getaway on ~10 Acres in The Piney Woods!

Secluded Getaway on ~10 Acres in The Piney Woods!

Secluded Getaway on ~10 Acres in The Piney Woods!
3.0 star property
Winnsboro
Secluded Getaway on ~10 Acres in The Piney Woods!
House (4 Bedrooms) | Interior
Tranquil Family Retreat: 4 Mi to Dtwn Winnsboro!

Tranquil Family Retreat: 4 Mi to Dtwn Winnsboro!

Tranquil Family Retreat: 4 Mi to Dtwn Winnsboro!
3.0 star property
Winnsboro
Tranquil Family Retreat: 4 Mi to Dtwn Winnsboro!
House (3 Bedrooms) | Interior
Lakefront Gladewater Retreat w/ Dock + Hot Tub!

Lakefront Gladewater Retreat w/ Dock + Hot Tub!

Lakefront Gladewater Retreat w/ Dock + Hot Tub!
3.0 star property
Gladewater
Lakefront Gladewater Retreat w/ Dock + Hot Tub!
House (2 Bedrooms) | Interior
Winnsboro Barndominium w/ Fire Pit & Large Deck!

Winnsboro Barndominium w/ Fire Pit & Large Deck!

Winnsboro Barndominium w/ Fire Pit & Large Deck!
3.0 star property
Winnsboro
10.0 out of 10, Exceptional, (2)
"The house was very clean and the furnishings were all updated. "
United States
Diane
Winnsboro Barndominium w/ Fire Pit & Large Deck!
House (2 Bedrooms) | Front of property
Renovated 'carnegie Cottage' - Walk to Dtwn!

Renovated 'carnegie Cottage' - Walk to Dtwn!

Renovated 'carnegie Cottage' - Walk to Dtwn!
3.0 star property
Winnsboro
10.0 out of 10, Exceptional, (2)
"Great historical feel with all the current updates and amenities! It was so nice and cozy. The decor was beautiful and promoted local artists. A lovely cottage that we would highly recommend."
United States
Sakinna
Renovated 'carnegie Cottage' - Walk to Dtwn!
House (2 Bedrooms) | Front of property
Walk to Downtown: Winnsboro Historic Home!

Walk to Downtown: Winnsboro Historic Home!

Walk to Downtown: Winnsboro Historic Home!
3.0 star property
Winnsboro
Walk to Downtown: Winnsboro Historic Home!
House (3 Bedrooms) | Interior
Winnsboro Lake Retreat: On-site Swimming & Fishing

Winnsboro Lake Retreat: On-site Swimming & Fishing

Winnsboro Lake Retreat: On-site Swimming & Fishing
3.0 star property
Winnsboro
9.0 out of 10, Wonderful, (2)
"The house is amazing, and the host communicated well and every question or issue was resolved! I look forward to staying there again!"
United States
john
Winnsboro Lake Retreat: On-site Swimming & Fishing
House (3 Bedrooms) | Interior
Horses Welcome: Pittsburg Home Near Wineries!

Horses Welcome: Pittsburg Home Near Wineries!

Horses Welcome: Pittsburg Home Near Wineries!
3.0 star property
Pittsburg
Horses Welcome: Pittsburg Home Near Wineries!
House (1 Bedroom) | Property grounds
'little Lucky Star' w/ Pond, Boat & Pasture View!

'little Lucky Star' w/ Pond, Boat & Pasture View!

'little Lucky Star' w/ Pond, Boat & Pasture View!
3.0 star property
Winnsboro
'little Lucky Star' w/ Pond, Boat & Pasture View!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upshur County Hotel Reviews

Contessa Inn

Contessa Inn

10/10 Excellent
"Yes"
Sonda 6-night trip
Posted 9 days ago
Contessa Inn
Garner Hotel Longview South by IHG

Garner Hotel Longview South by IHG

10/10 Excellent
"It was clean and great location."
Korey 4-night trip
Posted 11 days ago
Garner Hotel Longview South by IHG