Holiday Homes in Winston-Salem

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Winston-Salem and around

Barn Loft with Mountain Views, minutes from Hanging Rock State Park
Terrace/patio

Barn Loft with Mountain Views, minutes from Hanging Rock State Park

10.0 out of 10, Exceptional, (125)
"Beautiful piece of land overlooking mountains and pastures. We were there to hike and found the location perfect! After a long hike we came back to gorgeous grounds- Easy to grill out with views on all side. Owner was easy to communicate with. We would stay here again :)"
Barn Loft with Mountain Views, minutes from Hanging Rock State Park
Charming 3-bedroom home on beautiful High Rock Lake with Private Boat Dock
Fridge, microwave, oven, stovetop

Charming 3-bedroom home on beautiful High Rock Lake with Private Boat Dock

2.0 star property
9.6 out of 10, Exceptional, (12)
"Enjoyed our stay "
Charming 3-bedroom home on beautiful High Rock Lake with Private Boat Dock
The Cook's Wall Cabin
Terrace/patio

The Cook's Wall Cabin

9.8 out of 10, Exceptional, (115)
"Great location, perfect little cabin for visiting Hanging Rock State Park."
The price is €98
includes taxes & fees
20 Aug - 21 Aug
The Cook's Wall Cabin
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Terrace/patio

⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

9.8 out of 10, Exceptional, (55)
"The property was cozy, clean, and a great location for what we needed. "
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Beautiful 3 Bedroom Townhouse
Private kitchen

Beautiful 3 Bedroom Townhouse

10.0 out of 10, Exceptional, (35)
"Clean, spacious and quiet."
Beautiful 3 Bedroom Townhouse
Charming & Modern Home / Prime Location / Sleeps 8
Fridge, microwave, oven, stovetop

Charming & Modern Home / Prime Location / Sleeps 8

9.2 out of 10, Wonderful, (7)
"Great stay and the property was pictured exactly how it was. Perfect for our family as we visited our oldest who is living in Winston-Salem."
Charming & Modern Home / Prime Location / Sleeps 8
Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain
Exterior

Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain

8.6 out of 10, Excellent, (15)
"We had a great stay for a quick trip to see family! "
The price is €183
includes taxes & fees
18 Aug - 19 Aug
Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain
Spacious Townhouse In High Point Near HPU & Furniture Market
Fridge, microwave, oven, stovetop

Spacious Townhouse In High Point Near HPU & Furniture Market

2.0 star property
9.4 out of 10, Exceptional, (6)
"A beautiful updated townhouse. The master bedroom gave spa by vibe. enjoyable"
The price is €262
includes taxes & fees
18 Aug - 19 Aug
Spacious Townhouse In High Point Near HPU & Furniture Market
Gorgeous Hot Tub 4BR: Ideal for Market, HPU & Family Fun!
Pool

Gorgeous Hot Tub 4BR: Ideal for Market, HPU & Family Fun!

8.8 out of 10, Excellent, (21)
"This was in a great location for us while visiting our son for family weekend at High Point. The house is extremely comfortable and clean with everything we needed. Thank you! "
The price is €370
includes taxes & fees
22 Aug - 23 Aug
Gorgeous Hot Tub 4BR: Ideal for Market, HPU & Family Fun!
Family Sized Home sleeps 12 w/ king bed, near hospitals huge fenced yard
Smart TV

Family Sized Home sleeps 12 w/ king bed, near hospitals huge fenced yard

9.0 out of 10, Wonderful, (2)
"The fenced in yard was ginormous and flat. My two dogs loved the extra room to run and play fetch. The fence was a little broken in places but not enough that my dogs could get out (even if they tried). The tub in the master bedroom was very nice! Overall the house was comfortable and clean"
Family Sized Home sleeps 12 w/ king bed, near hospitals huge fenced yard
Charming home, dog friendly, with great location and mountain views
Fridge, microwave, oven, stovetop

Charming home, dog friendly, with great location and mountain views

2.0 star property
10.0 out of 10, Exceptional, (21)
"Lovely place to stay while visiting relatives who live nearby. Appreciated the coffee bar. Will definitely stay again."
Charming home, dog friendly, with great location and mountain views
12 minutes to Wet 'n Wild Water Park! Family-sized 3 bedroom cozy happy home!
Fridge, microwave, oven, stovetop

12 minutes to Wet 'n Wild Water Park! Family-sized 3 bedroom cozy happy home!

9.6 out of 10, Exceptional, (16)
"My family and I stayed here for a soccer tournament. It was close to fileds and great location for food and groceries!"
12 minutes to Wet 'n Wild Water Park! Family-sized 3 bedroom cozy happy home!
Charming 3-bedroom house in Winston-Salem with AC, WiFi
Exterior detail

Charming 3-bedroom house in Winston-Salem with AC, WiFi

Charming 3-bedroom house in Winston-Salem with AC, WiFi
Modern Bungalow | Game Room | Fire Pit | Grill
Fridge, microwave, oven, stovetop

Modern Bungalow | Game Room | Fire Pit | Grill

10.0 out of 10, Exceptional, (1)
"This property was clean and neat. The house had everything we needed and was in a great location. We would stay here again. "
The price is €316
includes taxes & fees
19 Aug - 20 Aug
Modern Bungalow | Game Room | Fire Pit | Grill
Quiet, newly renovated. Near everything!
Fridge, microwave, oven, stovetop

Quiet, newly renovated. Near everything!

9.8 out of 10, Exceptional, (10)
"My son was graduating from NC state but lives in Winston Salem. This was the perfect spot for 5 adults and served as a great base camp. There were many small touches included and communication was immediate. We would definitely stay here again! "
The price is €240
includes taxes & fees
24 Aug - 25 Aug
Quiet, newly renovated. Near everything!
Pet-Friendly Paradise w/ Private Dock in Lexington
Outdoor dining

Pet-Friendly Paradise w/ Private Dock in Lexington

10.0 out of 10, Exceptional, (4)
"This was the perfect getaway for my solo retreat - just me and my pup! The place was spacious and comfortable. And I really appreciated the workout nook! I loved spending mornings and evenings looking out at the lake. It was a wonderful stay!"
Pet-Friendly Paradise w/ Private Dock in Lexington
High ceiling house close to downtown
3 bedrooms, free WiFi

High ceiling house close to downtown

7.8 out of 10, Good, (8)
"Our stay was excellent! The host was very courteous and helped out a lot. The house was very clean and the beds very comfortable. My family and I really enjoyed our trip and we would recommend this property to those who want a comfortable stay at a great price."
The price is €168
includes taxes & fees
17 Aug - 18 Aug
High ceiling house close to downtown
Lakefront Getaway: Dock, Kayaks, Fire Pit, 70" TV
Property grounds

Lakefront Getaway: Dock, Kayaks, Fire Pit, 70" TV

10.0 out of 10, Exceptional, (33)
"My husband & I had an amazing time at this cute lake house! The house was clean & had cute decor as well as p"
Lakefront Getaway: Dock, Kayaks, Fire Pit, 70" TV
The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges.
Outdoor dining

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

10.0 out of 10, Exceptional, (48)
"Conveniently located, clean, nice decorated,and all the comforts of home."
The Coliseum Cottage. 1 King/ 2 Queen Beds. Close to coliseum and colleges.
Cozy golden gate cutie
Outdoor dining

Cozy golden gate cutie

9.8 out of 10, Exceptional, (17)
"Owner accessible and responsive… easy access to Greensboro downtown "
Cozy golden gate cutie
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 Winston-Salem Hotel Reviews

The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

10/10 Excellent
"The Brookstown Inn is our favorite place to stay when visiting Winston Salem. We have stayed multiple times and it’s always great! The front desk staff are friendly and helpful and make you feel welcome. The historical feel of the property is nice and the rooms are spacious and comfortable. The hotel has a great breakfast, wine and cheese hour and milk and cookies at night. We always enjoy our stay here!"
Ashley 1-night trip
Posted 9 hours ago
The Historic Brookstown Inn, Trademark Collection by Wyndham