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Winston - Salem Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winston - Salem holiday rentals

Exterior
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
Winston-Salem
8.0 out of 10, Very good, (1)
"House was clean and amenities were good. House is in a great location. Be aware that there is another rental unit downstairs that may have other parties occuppying."
United States
Elizabeth
The price is HK$989
HK$2,284 total
includes taxes & fees
11 Jan - 12 Jan 2026
King Beds Hot Tub Arcade Grill & Firepit
Exterior
3 mins from Downtown - PS5, King Bed & EV Charger

3 mins from Downtown - PS5, King Bed & EV Charger

3 mins from Downtown - PS5, King Bed & EV Charger
2.0 star property
Winston-Salem
8.8 out of 10, Excellent, (13)
"Everything was exactly like we expected it! Great stay."
United States
Tim K.
The price is HK$714
HK$1,510 total
includes taxes & fees
26 Dec - 27 Dec
3 mins from Downtown - PS5, King Bed & EV Charger
Interior
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
2.0 star property
Winston Salem
10.0 out of 10, Exceptional, (1)
"The room is clean, quiet, and cozy. I could tell my hosts had thought very carefully about what a guest may need, and they covered all those bases and more. Located in a quiet neighborhood very close to restaurants, grocery stores, etc."
United States
William L.
The price is HK$474
HK$1,327 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Interior
Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is HK$1,236
HK$3,537 total
includes taxes & fees
28 Dec - 29 Dec
Cozy Cottage: Nature-filled Winston-salem Retreat!
Interior
4-bedroom house in lovely High Point with AC, fitness room

4-bedroom house in lovely High Point with AC, fitness room

4-bedroom house in lovely High Point with AC, fitness room
2.0 star property
Deep River
The price is HK$693
HK$1,358 total
includes taxes & fees
28 Dec - 29 Dec
4-bedroom house in lovely High Point with AC, fitness room
Outdoor dining
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Winston-Salem
9.6 out of 10, Exceptional, (5)
"The cottage was super cozy; I absolutely loved it. Although our stay was short, I enjoyed it very much because of this cottage and Katy. Katy made sure we had everything we needed at all times, and she was an amazing host. I definitely would recommend this VRBO experience to anyone and everyone!"
United States
Tori B.
The price is HK$350
HK$791 total
includes taxes & fees
30 Dec - 31 Dec
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
BBQ/picnic Area
Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.0 star property
Kernersville
The price is HK$1,488
HK$2,265 total
includes taxes & fees
28 Dec - 29 Dec
Exec Suite King Bed Hot Tub Gym Laundry
Fridge, microwave, oven, stovetop
Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
2.0 star property
Winston-Salem
9.0 out of 10, Wonderful, (2)
"Absolutely spotless and adorable cottage with tons of room, with a layout that makes it appear more spacious than its stated square footage. The decor is cozy and welcoming, with board games galore in the living room. Loved the spacious dining table with bench. Both showers are gigantic and tiled beautifully. We chose the dual-head shower in the spacious back bedroom, which easily holds 2 queen beds and furniture, as we chose to sleep there instead of the front bedroom. The mattress was very...
United States
Steven A.
The price is HK$670
HK$1,960 total
includes taxes & fees
25 Jan - 26 Jan 2026
Chic 2BR/2BA Near Dining & Shops
Interior
Downtown Charm, 3 Bdr, Near Rest and Bars

Downtown Charm, 3 Bdr, Near Rest and Bars

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (19)
"Wonderful place to stay…ecotourism need!"
United Kingdom
Patricia K.
The price is HK$670
HK$1,948 total
includes taxes & fees
19 Jan - 20 Jan 2026
Downtown Charm, 3 Bdr, Near Rest and Bars
In-room dining
Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
Winston-Salem
8.0 out of 10, Very good, (1)
"The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt...
United States
Rami
The price is HK$1,232
HK$2,391 total
includes taxes & fees
11 Jan - 12 Jan 2026
Heated Pool King Bed Jacuzzi Bath Arcade
Fridge, microwave, oven, stovetop
Cute cottage in a rural setting

Cute cottage in a rural setting

Cute cottage in a rural setting
Clemmons
7.6 out of 10, Good, (8)
"Enjoyed staying in North Carolina. The location of the Cottage is great. Close to shopping and different tourist attractions throughout NC. The Cottage could use some updating, but overall it was comfortable, like going to visit Grandma!! Thank you for letting my family and I stay in the Cottage for the week."
United States
Annette B.
The price is HK$721
HK$2,302 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cute cottage in a rural setting
Fridge, microwave, oven, stovetop
Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
2.0 star property
Winston-Salem
The price is HK$612
HK$1,783 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy 3BR Home Near Fairgrounds and Downtown
Property grounds
Cozy Secluded Cabin on 50 Acre Horse Ranch

Cozy Secluded Cabin on 50 Acre Horse Ranch

Cozy Secluded Cabin on 50 Acre Horse Ranch
Mocksville
10.0 out of 10, Exceptional, (45)
"Property was a cabin, very clean & amenities shared. Wonderful nuggets that welcomed their guests. Pet friendly with trail to walk our dogs. Highly recommend "
United States
Sharon A.
The price is HK$972
HK$1,929 total
includes taxes & fees
28 Dec - 29 Dec
Cozy Secluded Cabin on 50 Acre Horse Ranch
Exterior detail
Minimalist Stay

Minimalist Stay

Minimalist Stay
Winston-Salem
10.0 out of 10, Exceptional, (2)
"Perfect place to stay. Great home base for appointments."
United States
Patricia K.
The price is HK$778
HK$1,397 total
includes taxes & fees
30 Dec - 31 Dec
Minimalist Stay
Exterior
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Winston-Salem
9.4 out of 10, Exceptional, (6)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
The price is HK$1,113
HK$1,969 total
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Fridge, microwave, oven, stovetop
Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
Winston-Salem
The price is HK$1,353
HK$3,474 total
includes taxes & fees
5 Jan - 6 Jan 2026
Arcade Kid Friendly Firepit Grill HotTub
Outdoor dining
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.8 out of 10, Exceptional, (17)
"Wonderful stay! "
United States
Hannah J.
The price is HK$700
HK$1,634 total
includes taxes & fees
26 Dec - 27 Dec
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Smart TV
Charming 2-bed, 2 full bath studio with WiFi, AC in Ardmore

Charming 2-bed, 2 full bath studio with WiFi, AC in Ardmore

Charming 2-bed, 2 full bath studio with WiFi, AC in Ardmore
Winston-Salem
10.0 out of 10, Exceptional, (3)
"We really enjoyed this cozy comfortable pet friendly place. It was quite, clean and had everything we needed! Central location to all restaurants and other places. We will rebook if needed. The host was easy to reach and responded timely. Great spot and very clean!"
United States
kevin C.
The price is HK$894
HK$2,135 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bed, 2 full bath studio with WiFi, AC in Ardmore
Fridge, microwave, oven, stovetop
Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (21)
"Great place to stay for a quick family visit. "
United States
karen e.
The price is HK$902
HK$2,004 total
includes taxes & fees
1 Jan - 2 Jan 2026
Quiet, newly renovated. Near everything!
Terrace/patio
Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
Winston-Salem
The price is HK$1,176
HK$3,265 total
includes taxes & fees
7 Jan - 8 Jan 2026
Winston Sleeps 16 - 2 Kitchens Hot Tub
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

Hampton Inn Winston-Salem Hanes Mall

Hampton Inn Winston-Salem Hanes Mall

10/10 Excellent
"The hotel was decorated nicely for Christmas, the room was clean and the staff were very friendly!"
Tina 1-night trip
Posted 4 days ago
Hampton Inn Winston-Salem Hanes Mall

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