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Search Vacation Homes in Winston - Salem

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Our top choices for Winston - Salem vacation homes

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
$159 nightly
The price is $175
Dec 24 - Dec 25
Total with taxes and fees
4-bedroom house in lovely High Point with AC, fitness room
Dining
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.
$236 nightly
The price is $251
Jan 20 - Jan 21, 2026
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
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.
$238 nightly
The price is $253
Jan 8 - Jan 9, 2026
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
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
$216 nightly
The price is $229
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cozy 3BR Home Near Fairgrounds and Downtown
Exterior
5 mins to downtown 3 Kings Old Salem Sanctuary

5 mins to downtown 3 Kings Old Salem Sanctuary

5 mins to downtown 3 Kings Old Salem Sanctuary
2.0 star property
Winston-Salem
$303 nightly
The price is $345
Jan 5 - Jan 6, 2026
Total with taxes and fees
5 mins to downtown 3 Kings Old Salem Sanctuary
TV, offices
Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi

Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi

Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi
2.0 star property
Winston-Salem
$291 nightly
The price is $329
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern 2BR near WFU Steps to LJVM Coliseum Family-Friendly & Fast WiFi
Property grounds
The Cook's Wall Cabin

The Cook's Wall Cabin

The Cook's Wall Cabin
Germanton
9.8 out of 10, Exceptional, (128)
"Hosts were super friendly and informative Clean and very comfortable Toilet area is small but everything we needed and more was there for the affordable price Would stay again "
United States
Terri
$103 nightly
The price is $110
Dec 22 - Dec 23
Total with taxes and fees
The Cook's Wall Cabin
Fridge, microwave, dishwasher, ice maker
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.
$159 nightly
The price is $180
Dec 22 - Dec 23
Total with taxes and fees
Minimalist Stay
Terrace/patio
Cozy 2-bedroom bungalow in lovely Winston-Salem

Cozy 2-bedroom bungalow in lovely Winston-Salem

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (13)
"Perfect location and will definitely stay there again. Host answered questions promptly."
United States
Donna B.
$229 nightly
The price is $259
Jan 2 - Jan 3, 2026
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
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.
$235 nightly
The price is $266
Dec 22 - Dec 23
Total with taxes and fees
Quiet, newly renovated. Near everything!
Exterior
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.
$188 nightly
The price is $212
Dec 22 - Dec 23
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Smart TV, books
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital

Three bedroom 5 minutes to state university & town, 10 min to baptist hospital

Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
Winston-Salem
8.4 out of 10, Very Good, (15)
"Great stay with family. "
United States
Tyler J.
$196 nightly
The price is $221
Dec 30 - Dec 31
Total with taxes and fees
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
Fridge, microwave, oven, stovetop
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.6 out of 10, Exceptional, (9)
"Nice location "
United States
Benelli T.
$270 nightly
The price is $305
Dec 22 - Dec 23
Total with taxes and fees
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Fridge, microwave, oven, stovetop
La Casita: A Cozy Retreat Near Wake Forest University"

La Casita: A Cozy Retreat Near Wake Forest University"

La Casita: A Cozy Retreat Near Wake Forest University"
Winston-Salem
9.6 out of 10, Exceptional, (51)
"Very nice place to stay! "
United States
Kirby M.
$220 nightly
The price is $249
Jan 11 - Jan 12, 2026
Total with taxes and fees
La Casita: A Cozy Retreat Near Wake Forest University"
2 bedrooms, desk, iron/ironing board, travel crib
Quiet home in the Kernersville near Winston Salem, Greensboro, High Point

Quiet home in the Kernersville near Winston Salem, Greensboro, High Point

Quiet home in the Kernersville near Winston Salem, Greensboro, High Point
Kernersville
10.0 out of 10, Exceptional, (65)
"Well kept place just as listed. Owners were very helpful when asked. Recommend for small families!"
United States
Justin D.
$205 nightly
The price is $231
Dec 22 - Dec 23
Total with taxes and fees
Quiet home in the Kernersville near Winston Salem, Greensboro, High Point
Bar (on property)
Vintage Modern Synthesis in the Heart of Winston-Salem

Vintage Modern Synthesis in the Heart of Winston-Salem

Vintage Modern Synthesis in the Heart of Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (42)
"Great property, great location and very helpful owners"
United States
Simon P.
$243 nightly
The price is $275
Dec 22 - Dec 23
Total with taxes and fees
Vintage Modern Synthesis in the Heart of Winston-Salem
Smart TV
3 bed 2 bath single level home in Kernersville

3 bed 2 bath single level home in Kernersville

3 bed 2 bath single level home in Kernersville
Kernersville
9.6 out of 10, Exceptional, (35)
"We needed a place to stay halfway on our trip to the beach! We could not have asked for a nicer, easier to get to spot! We really enjoyed our stay! "
United States
Dylan V.
$257 nightly
The price is $290
Jan 3 - Jan 4, 2026
Total with taxes and fees
3 bed 2 bath single level home in Kernersville
Microwave, oven, stovetop, dishwasher
Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants

Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants

Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants
Winston-Salem
10.0 out of 10, Exceptional, (1)
"Very nice host with a nice welcoming home. The house is located in a area where it is easy to hit the heart of winston salem and get good food, have fun and enjoy your stay! "
United States
Joseph G.
$316 nightly
The price is $357
Dec 29 - Dec 30
Total with taxes and fees
Soothing 3-bedroom house with AC in Winston-Salem close to highway restaurants
Interior
Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Winston-Salem
9.2 out of 10, Wonderful, (9)
"An outstanding property.Well-appointed, clean, convenient to everything, and most importantly, quiet and peacefulWe are definitely staying again."
United States
Robert B.
$241 nightly
The price is $257
Jan 12 - Jan 13, 2026
Total with taxes and fees
Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Exterior
Cozy Winston-Salem Vacation Cabin

Cozy Winston-Salem Vacation Cabin

Cozy Winston-Salem Vacation Cabin
2.0 star property
Winston-Salem
8.4 out of 10, Very Good, (5)
"Host was prompt with responses and willing to assist. Sleeping for 10 or 12 if required but semi-comfortable seating for maybe 4 people unless you count dining room seating. Water pressure very low. Outdoor area and deck had nice view but old and could use some TLC with a covered are for rain days. We left a day early and went to a hotel."
Canada
John C.
$409 nightly
The price is $462
Dec 22 - Dec 23
Total with taxes and fees
Cozy Winston-Salem Vacation Cabin
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 & Suites Winston-Salem/University Area, NC

Hampton Inn & Suites Winston-Salem/University Area, NC

10/10 Excellent
"Breakfast was good, service was great, property is clean, bed was comfortable."
Jeff 1-night trip
Posted 17 hours ago
Hampton Inn & Suites Winston-Salem/University Area, NC

Find out more about Winston - Salem

Winston - Salem Vacation Homes information

Number of reviews
423
Accommodation
242 Vacation Homes
Lowest Price
$110
Highest Price
$462

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