Book Holiday Homes in Winston-Salem

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Featured Holiday Homes in Winston-Salem

Charming Remodeled 4 Bedroom Home in Downtown High Point

Charming Remodeled 4 Bedroom Home in Downtown High Point

High Point
A stay at this vacation home places you in the heart of High Point, steps from World's Largest Chest of Drawers and 6 minutes by foot from Wake Forest Baptist ...
Charming Remodeled 4 Bedroom Home in Downtown High Point
The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges.

The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges.

Greensboro
With a stay at this vacation home in Greensboro, you'll be within a 15-minute walk of Greensboro Coliseum and White Oak Amphitheatre.
The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges.
High Point's Gem!  Group Friendly!  Five Bedrooms! Pet Friendly!

High Point's Gem! Group Friendly! Five Bedrooms! Pet Friendly!

2 out of 5
High Point
Located in High Point (Deep River), this vacation home is within a 5-minute drive of Oak Hollow Lake and Erick Andersen.
High Point's Gem! Group Friendly! Five Bedrooms! Pet Friendly!
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Beautiful 3 Bedroom Townhouse

Beautiful 3 Bedroom Townhouse

Greensboro
With a stay at this vacation home in Greensboro, you'll be within a 10-minute drive of Greensboro Coliseum and Guilford College.
Beautiful 3 Bedroom Townhouse
Hot Tub - Chefs Kitchen-Fenced Yard- Historic Home

Hot Tub - Chefs Kitchen-Fenced Yard- Historic Home

Greensboro
The price is AU$955 per night from 30 Dec to 31 Dec
AU$955
includes taxes & fees
30 Dec - 31 Dec
With a stay at this vacation home in Greensboro (Fisher Park), you'll be within a 10-minute drive of Greensboro Coliseum and Lebauer Health Care System.
Hot Tub - Chefs Kitchen-Fenced Yard- Historic Home
Mins from PTI Airport/Triad Park/market

Mins from PTI Airport/Triad Park/market

Colfax
With a stay at this vacation home in Colfax (Deep River), you'll be a 3-minute drive from Piedmont Triad Farmers Market and 7 minutes from Kernersville ...
Mins from PTI Airport/Triad Park/market
The Lakeview House - access to pier/dock, fire pit and lake access

The Lakeview House - access to pier/dock, fire pit and lake access

Lexington
With a stay at this vacation home, you'll be centrally located in Lexington, within a 15-minute drive of High Rock Lake and Wake Forest Baptist Med Center.
The Lakeview House - access to pier/dock, fire pit and lake access
Bright Greensboro Escape ~ 1 Mi to Downtown

Bright Greensboro Escape ~ 1 Mi to Downtown

Greensboro
With a stay at this vacation home in Greensboro (Fisher Park), you'll be within a 10-minute drive of Greensboro Coliseum and Steven Tanger Center for the Performing ...
Bright Greensboro Escape ~ 1 Mi to Downtown
Shalimar Estates @ Emerywood and Downtown/HPU

Shalimar Estates @ Emerywood and Downtown/HPU

High Point
The price is AU$1,714 per night from 12 Jan to 13 Jan
AU$1,714
includes taxes & fees
12 Jan - 13 Jan 2025
Located in High Point, this vacation home is within a 10-minute drive of International Home Furnishings Center and Cornerstone Health Care.
Shalimar Estates @ Emerywood and Downtown/HPU
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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.

Winston-Salem Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winston-Salem vacation homes are the perfect way for you to wing it.

Holiday houses in Winston-Salem let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winston-Salem in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winston-Salem adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winston-Salem with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winston-Salem vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winston-Salem Holiday Homes essential information

Accommodation
478 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$1,714
Popular accommodation
Charming Remodeled 4 Bedroom Home in Downtown High Point, The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges. , High Point's Gem! Group Friendly! Five Bedrooms! Pet Friendly!, Beautiful 3 Bedroom Townhouse, Hot Tub - Chefs Kitchen-Fenced Yard- Historic Home, Mins from PTI Airport/Triad Park/market, The Lakeview House - access to pier/dock, fire pit and lake access, Bright Greensboro Escape ~ 1 Mi to Downtown, Shalimar Estates @ Emerywood and Downtown/HPU

Top trending hotels in Winston-Salem

Best Western Plus University Inn

Best Western Plus University Inn

3.5 out of 5
3050 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 25 Dec to 26 Dec
AU$121
includes taxes & fees
25 Dec - 26 Dec
With a stay at Best Western Plus University Inn, you'll be centrally located in Winston-Salem, a 1-minute drive from Wake Forest University and 10 minutes from ...
Best Western Plus University Inn
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
420 High St, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 24 Dec to 25 Dec
AU$137
includes taxes & fees
24 Dec - 25 Dec
With a stay at Hawthorne Inn and Conference Center in Winston-Salem, you'll be in the historical district, within a 10-minute drive of Hanes Mall and Benton ...
Hawthorne Inn and Conference Center
La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

2.5 out of 5
2020 Griffith Rd, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 30 Dec to 31 Dec
AU$115
includes taxes & fees
30 Dec - 31 Dec
When you stay at La Quinta Inn & Suites by Wyndham Winston-Salem in Winston-Salem, you'll be in a shopping district, within a 15-minute drive of Hanes Mall and ...
La Quinta Inn & Suites by Wyndham Winston-Salem
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Comfort Suites Hanes Mall

Comfort Suites Hanes Mall

2.5 out of 5
200 Capitol Lodging Ct, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 24 Dec to 25 Dec
AU$166
includes taxes & fees
24 Dec - 25 Dec
With a stay at Comfort Suites Hanes Mall in Winston-Salem, you'll be in the business district, within a 5-minute drive of Hanes Mall and Wilkes Regional.
Comfort Suites Hanes Mall
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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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^Subject to availability and chosen travel dates.