Holiday Homes in Winston - Salem

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Winston - Salem and around

Barn Loft with Mountain Views, minutes from Hanging Rock State Park
Enjoy a serene view from the deck, where you can sit and relax with a table and chairs.

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

10.0 out of 10, Exceptional, (124)
"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
The Cook's Wall Cabin
Sit by the fire pit in a serene outdoor setting, surrounded by natural beauty.

The Cook's Wall Cabin

9.8 out of 10, Exceptional, (114)
"Great location, perfect little cabin for visiting Hanging Rock State Park."
The price is €99
includes taxes & fees
5 Aug - 6 Aug
The Cook's Wall Cabin
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
Cozy living space with a fireplace, sofa, and coffee table.

Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem

10.0 out of 10, Exceptional, (62)
"House was perfection, and awesome location close to everything. "
Remodeled historic home! Steps away from dining & shops - Easy walk to Old Salem
Quiet, newly renovated. Near everything!
Enjoy cooking in this well-equipped kitchen with a central island and barstools.

Quiet, newly renovated. Near everything!

9.8 out of 10, Exceptional, (9)
"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 €241
includes taxes & fees
10 Aug - 11 Aug
Quiet, newly renovated. Near everything!
High ceiling house close to downtown
Cozy retreat with a single bed, bedside table, and ceiling fan.

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 €171
includes taxes & fees
5 Aug - 6 Aug
High ceiling house close to downtown
3 bedrooms 7min from downtown, college and hospital
Two-story house with a covered porch and garden.

3 bedrooms 7min from downtown, college and hospital

9.6 out of 10, Exceptional, (5)
"I had a great stay! It was a nice place for my small family. Our flight ended up getting delayed so the host was nice enough to let us stay a little longer than check out time. Definitely will book again when I come to NC "
The price is €209
includes taxes & fees
4 Sept - 5 Sept
3 bedrooms 7min from downtown, college and hospital
Treetop - 3 King Suites- sister property next door #1559015
Enter a charming outdoor space with a stone-clad door, wooden beams, and a covered porch area.

Treetop - 3 King Suites- sister property next door #1559015

10.0 out of 10, Exceptional, (22)
"Beautiful and peaceful property with everything you need in the house and nearby. I highly recommend staying here for any visit into the WS area. "
The price is €476
includes taxes & fees
5 Aug - 6 Aug
Treetop - 3 King Suites- sister property next door #1559015
Vintage Modern Synthesis in the Heart of Winston-Salem
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a dining area.

Vintage Modern Synthesis in the Heart of Winston-Salem

10.0 out of 10, Exceptional, (40)
"Great property, great location and very helpful owners"
The price is €243
includes taxes & fees
5 Aug - 6 Aug
Vintage Modern Synthesis in the Heart of Winston-Salem
3 bed 2 bath single level home in Kernersville
Cozy living room with a central fireplace, flat-screen TV, and comfortable seating area.

3 bed 2 bath single level home in Kernersville

9.6 out of 10, Exceptional, (32)
"This was the second time we have stayed at this house - it's super clean, beds are comfortable, great fenced in yard and in a great location. We will definitely be staying here again!"
The price is €244
includes taxes & fees
5 Aug - 6 Aug
3 bed 2 bath single level home in Kernersville
Downtown Charm, 3 Bdr, Near Rest and Bars, Downtown Charm, 3 Bdr, Near Rest and Bars
Enjoy meals and gatherings in the dining area with a wooden table and benches, and take in the views from the large window with blinds.

Downtown Charm, 3 Bdr, Near Rest and Bars, Downtown Charm, 3 Bdr, Near Rest and Bars

9.4 out of 10, Exceptional, (14)
"This space was perfect for three friends in town for a quick overnight stay. Plenty of space for everyone, very clean and well equipped."
Downtown Charm, 3 Bdr, Near Rest and Bars, Downtown Charm, 3 Bdr, Near Rest and Bars
Home w/ Large Yard: 6 Mi to Dtwn Winston-Salem!
Step out onto the porch and enjoy the serene surroundings.

Home w/ Large Yard: 6 Mi to Dtwn Winston-Salem!

9.8 out of 10, Exceptional, (9)
"The place was spacy, quite and very clean. Beds were very comfortable The agent, Amenda was very communicator and also very accommodating. We enjoyed staying at 'Willow Haven' "
Home w/ Large Yard: 6 Mi to Dtwn Winston-Salem!
Mins from PTI Airport/Triad Park/market
Relax in a spacious bedroom with a large bed, ceiling fan, and wall-mounted TV.

Mins from PTI Airport/Triad Park/market

9.0 out of 10, Wonderful, (15)
"Thank you so much for the easy and nice stay"
Mins from PTI Airport/Triad Park/market
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Enjoy cooking in this well-equipped kitchen with a central island, stovetop, and oven.

Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem

9.0 out of 10, Wonderful, (2)
"Overall pleasant stay"
The price is €610
includes taxes & fees
5 Aug - 6 Aug
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Ideal Ardmore Location;Game Room;Hot Tub;BoHo Chic
Relax in a wicker chair on a deck surrounded by lush greenery.

Ideal Ardmore Location;Game Room;Hot Tub;BoHo Chic

9.8 out of 10, Exceptional, (7)
"Love your cozy cottage , it was exactly what I was looking for!"
Ideal Ardmore Location;Game Room;Hot Tub;BoHo Chic
Stunning 3-bedroom house near The Coliseum & Downtown
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and coffee maker.

Stunning 3-bedroom house near The Coliseum & Downtown

10.0 out of 10, Exceptional, (1)
"My daughter and I were in town for the weekend, for a local event and this home was only half a mile from the fairgrounds, very convenient and a very nice home.As the host noted, the home was completely remodeled, very clean and homey, loved the warm blue colors and they provided a bottle of wine, gotta love it! Upon arrival I had a few questions and the host was very timely with the responses and helpful!The back yard was clean and very spacious, and the front porch is enclosed, allowing for...
Stunning 3-bedroom house near The Coliseum & Downtown
Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
Kitchen area with island, dining space, and cozy seating area.

Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore

10.0 out of 10, Exceptional, (4)
"Property was great. Close to shops and interstate. Would definately stay again and recommend to anyone. "
The price is €407
includes taxes & fees
5 Aug - 6 Aug
Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
Sunset Cottage: Charming 2-bdrm house w/ king bed in WinstonSalem; great locatio
Kitchen features a double oven, microwave, and large refrigerator, with a window and wooden floor.

Sunset Cottage: Charming 2-bdrm house w/ king bed in WinstonSalem; great locatio

9.0 out of 10, Wonderful, (2)
Sunset Cottage: Charming 2-bdrm house w/ king bed in WinstonSalem; great locatio
Deacon Stays: The Idlewilde - Walk to WFU
Relax in this inviting living room with a stone fireplace, flat-screen TV, and comfortable seating areas.

Deacon Stays: The Idlewilde - Walk to WFU

10.0 out of 10, Exceptional, (20)
"Great place to stay with your family or friends."
Deacon Stays: The Idlewilde - Walk to WFU
Renovated historic Craftsman bungalow near Winston Salem and mountain activities
Escape to a serene oasis surrounded by lush greenery and a tranquil pond with a gentle waterfall.

Renovated historic Craftsman bungalow near Winston Salem and mountain activities

10.0 out of 10, Exceptional, (55)
"We loved the house! And, the hosts were fantastic! What a great experience!"
Renovated historic Craftsman bungalow near Winston Salem and mountain activities
La Casita: A Cozy Retreat Near Wake Forest University"
Stunning entrance with a black chandelier and potted plants.

La Casita: A Cozy Retreat Near Wake Forest University"

9.6 out of 10, Exceptional, (48)
"Great location WFU, Reynolda Rd. House very clean with well equipped kitchen. King size beds. Outdoor patio table and chairs "
The price is €229
includes taxes & fees
25 Aug - 26 Aug
La Casita: A Cozy Retreat Near Wake Forest University"
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winston - Salem Hotel Reviews

Kimpton Cardinal Hotel by IHG

Kimpton Cardinal Hotel by IHG

10/10 Excellent
"Great historic hotel, just a little pricey "
Tejal 2-night trip
Posted 8 hours ago
Kimpton Cardinal Hotel by IHG