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Winston-Salem vacation rentals

Vacation rentals in Winston-Salem by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.

Winston-Salem, known for its historic charm, features the living museum of Old Salem, the arts-focused Reynolda House Museum of American Art, and Wake Forest University's vibrant campus. Visitors flock to annual events like the National Black Theatre Festival, the RiverRun International Film Festival, and the colorful Art & Soul of the Piedmont. By booking on Houfy, you connect directly with hosts in Winston-Salem. Explore available rentals from classic historic homes to urban lofts, also convenient to nearby Greensboro and High Point. Fall hosts the popular Dixie Classic Fair, drawing in crowds for crafts, food, and entertainment.

Top-Rated Vacation Homes in Winston-Salem

Browse the highest rated vacation properties in Winston-Salem.

The Brookwood

4 bd·2 ba
5· 249

$1,311.11 USD total for 3 nights

Oct 11 – 14, 2026

Great Winston Salem / Wake Forest University stay
We selected this rental for the accommodation with pets. Daniel was very helpful in making some allowances for our unexpected travel with our dogs. Last minute, we had to leave them at home, but his flexibility was much appreciated and we will remember to consider the house for future travels with furry friends. The access to the house was straightforward, and everything was as described in the listing. Lots of room in a well maintained older home with modern amenities. The location is perfect for hanging out at nearby Wake Forest University, and I suspect it makes for a great graduation weekend stay. Daniel was responsive to all questions, and as noted, accommodating to a non-standard pet stay. Would definitely recommend!
M. B. · Stay May 2023

The Polo

4 bd·2 ba
5· 189

$805.10 USD total for 3 nights

Oct 5 – 8, 2026

Wonderful Baseball Weekend
Came up for our annual “Wake Weekend” with alumni of WF and former baseball players to enjoy a weekend. The house was perfect for us, as we had former college roommates and their families staying. As one of the wives from the group had been a volleyball player, staying at the “old volleyball house” was a real treat and throwback to the guys. The house was a GREAT location, within walking distance to Campus Gas, loved the huge backyard for the boys to play catch, really just the best. We will definitely be booking again for next year and the 25-year reunion of the Deacs winning the ACC baseball Championship! #godeacs!
L. B. · Stay April 2025

The Cottage

2 bd·2 ba
5· 146

$689.21 USD total for 3 nights

Oct 5 – 8, 2026

Superb location and property
This was the perfect location for our Winston Salem trip. Traveling with my 86 year old mother, the “step less “ entry, spacious interior and well equipped kitchen were perfect. The property is safe, quiet, and comfortable with a very nice ascetic. The location afforded easy access for visiting relatives in the area as well as restaurants, shopping, etc. The host was responsive to every question and request, which we truly appreciated.
D. B. · Stay November 2024

The Idlewilde

4 bd·3 ba
5· 150

$634.24 USD total for 3 nights

Sep 28 – Oct 1, 2026

Family fun in Wnston-Salem
I was looking for a home to rent for my husband and I and two grown children and their spouses for a family wedding at Reynolda Village. I wanted at least 3 bedrooms and baths and Daniel's home was just perfect. It had everything we needed, was close to everything in a lovely neighborhood. the home was comfortable, immaculate and Daniel was responsive and helpful. This is a great home for a family with little kids or big ones and I would highly recommend you choosing this home if you're in the Winston- Salem area.
L. R. · Stay April 2025

Double House - Sleeps 16 Walking Distance to WFU

6 bd·5 ba
5· 39

$1,689.26 USD total for 3 nights

Oct 5 – 8, 2026

Wonderful!
We had a great time as we met up with family for a Christmas celebration. We rented both the main house and the in-law suite. Both were fabulous! Very clean and had everything we needed. Loved that there were Christmas trees up in the homes. Very comfortable beds, lots of space, great location. The owner is super easy to work with and responded immediately to texts. The property is large with lots of yard space. Modern appliances, plenty of dishes, paper products and even little starter bars of soap. There aren’t any negatives about this property! Would definitely stay here again!
L. L. · Stay December 2022

The Oak Crest

4 bd·2 ba
5· 29

$812.78 USD total for 3 nights

Sep 28 – Oct 1, 2026

We had an amazing stay at this Airbnb! The location truly can’t be beat — it’s close to everything in Winston-Salem. I was able to walk or take a quick drive to great restaurants, bars, coffee shops, and all the main spots downtown. Super convenient! The space itself was clean, comfortable, and exactly as described. Check-in was smooth, parking was easy, and the host was extremely responsive and friendly. You can tell they put a lot of thought into making the place welcoming. If you’re looking for a spot that’s central, hassle-free, and perfect for exploring Winston-Salem, this is it. I’d definitely stay here again!
R. · Stay November 2025

$372.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

It was a pleasure and an experience we won't soon forget. From the moment we arrived, we were greeted with warmth and hospitality that set the tone for our entire stay. The Parkers are the epitome of gracious hosts. They went above and beyond to ensure that we felt welcome and comfortable during our stay. From providing helpful tips to ensuring that we had everything we needed for a relaxing stay, they were always available and eager to assist. The home itself was nothing short of fantastic. Conveniently located near Reynolda Village, easy access to all W-S has, while still providing a peaceful retreat away from the hustle and bustle of the city. The neighborhood was lovely and felt incredibly safe. The accommodations were top-notch. Immaculately clean and spacious. Overall, our experience at the Parkers was nothing short of exceptional. We couldn't have asked for better hosts or a more perfect place to stay during our time. We're already looking forward to our next stay with them!
C. · Stay February 2024

$670.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casie’s and Matt’s place was AMAZING!! We were there with 2 members of our Family for a Thanksgiving at my Other son’s place in Winston!! We had a blast.. the place is been remodeled with such attention to detail. All that is needed is there.. good Parking and a very cozy environment. Both Casie and Matt are Super Communicators, always asking if we needed anything! We had the visit of a 12 Point Beutifull Male Deer in the backyard! Great Place, Will definitely comeback when needed in Winston! Thank you Guys!!
D. · Stay November 2025

Recommended Homes in Winston-Salem

Handpicked properties we think you'll love in Winston-Salem.

The Double House at Brookwood

8 bd·4 ba
5· 2

$3,460.26 USD total for 3 nights

Oct 11 – 14, 2026

Why visit Winston-Salem

Discover what makes Winston-Salem a perfect vacation rental destination.

Rich Historical Heritage

Winston Salem's Old Salem is a living history museum.

Explore Old Salem Museums & Gardens, just 1.5 miles from downtown, where you can step back into the 18th century with costumed interpreters and preserved structures.

Vibrant Arts Scene

Home to the Southeastern Center for Contemporary Art.

SECCA, a mere 3 miles from the city center, offers rotating exhibits featuring local and national artists, making it a must-visit for art enthusiasts.

Culinary Delights

Local flavors at the Piedmont Triad Farmers Market.

Visit the Piedmont Triad Farmers Market, only 9 miles away, to sample fresh, regional produce and a variety of local delicacies.

Outdoor Adventures

Reynolda Gardens offers tranquility and beauty.

Stroll through Reynolda Gardens, just 2 miles from the city center, offering 129 acres of gardens and trails ideal for relaxation or a leisurely walk.

Where to stay in Winston-Salem

The best areas and neighborhoods for your vacation rental in Winston-Salem.

Downtown

The heart of the city, with a lively arts district and various dining options. Easy access to museums and theaters.

Best for: culture seekers, food lovers, night owls

West End

Historic district featuring charming Victorian homes and close proximity to the Hanes Park and Old Salem.

Best for: history buffs, families, walkers

Ardmore

A friendly residential area known for its early 20th-century architecture and proximity to Wake Forest University.

Best for: families, university visits, quiet stays

Buena Vista

An affluent neighborhood with tree-lined streets and grand houses, close to Reynolda Gardens and shopping areas.

Best for: luxury travelers, garden lovers, shoppers

Find Winston-Salem vacation rentals that suit your style

Vacation homes, cottages and more — pick the kind of Winston-Salem vacation rental you want, then book it direct with the host.

Winston-Salem vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Winston-Salem vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Winston-Salem

All within driving distance of Winston-Salem vacation rentals.

Old Salem Museums & Gardens

A living history museum illustrating the culture of the Moravians from the 18th century. · 1.5 miles

Reynolda House Museum of American Art

Features an impressive collection of American art from the colonial period to the present. · 3 miles

Reynolda Gardens

Offers diverse flora and miles of trails for nature walks. · 2 miles

SciWorks Science Center

Interactive science museum and planetarium perfect for family outings. · 6 miles

Southeastern Center for Contemporary Art

Hosts innovative and cutting-edge contemporary art exhibits. · 3 miles

Hanes Mall

One of the largest shopping complexes in the Carolinas, featuring over 200 stores. · 5 miles

Getting to and around Winston-Salem

Winston Salem offers easy access via road and air with convenient public transit options.

Nearby Airports
PIEDMONT TRIAD INTERNATIONAL AIRPORT
Located 25 miles from Winston Salem, offering flights on major airlines.
Public Transit
WSTA BUS SYSTEM
Offers daily routes throughout the city, making it easy to navigate Winston Salem.
Driving
RENTAL CARS
Available at Piedmont Triad International Airport and several locations downtown.

Similar vacation rentals near Winston-Salem

Homes within 60 miles of Winston-Salem, from verified hosts.

Shady Shoals - Lake Norman

4 bd· ba
5· 50

$1,243.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Newly renovated, clean, convenient, quiet & comfy

2 bd·2 ba
5· 517

$412.50 USD total for 3 nights

Sep 29 – Oct 2, 2026

Art, Beauty, Nature: A Woodland Retreat

1 bd·1 ba
4.86· 318

$802.24 USD total for 6 nights

Sep 28 – Oct 4, 2026

The Lodges at Buffalo Mountain

5 bd· ba
5· 1

$1,275.75 USD total for 3 nights

Sep 28 – Oct 1, 2026

Uwharrie Creekside Escape

3 bd·2 ba
5· 120

$710.60 USD total for 3 nights

Oct 4 – 7, 2026

Handmade Retreat

2 bd·1 ba
4.88· 209

$561.34 USD total for 3 nights

Sep 28 – Oct 1, 2026

Red Roof Cabin - Suite w/ Hot Tub & Mountain Views

1 bd·1 ba
5· 71

$770.00 USD $701.00 USD total for 3 nights

Oct 4 – 7, 2026

GIGGLING CREEK COTTAGE - 45 ACRES OF RURAL BLISS

2 bd·1 ba
4· 1

$442.20 USD total for 3 nights

Oct 4 – 7, 2026

Lake Norman Mansion - Live the Life of Royalty

7 bd·6 ba
5· 6

$6,298.20 USD total for 3 nights

Sep 28 – Oct 1, 2026

Spacious 4BR Home w/ Game Room and Backyard Oasis

4 bd·2 ba
5· 37

$601.00 USD total for 3 nights

Oct 4 – 7, 2026

Red Roof Cabin - Whole House Estate w/ Luxury View

4 bd·3 ba
5· 12

$1,755.00 USD total for 3 nights

Oct 5 – 8, 2026

Red Roof Cabin - Main House w/ Million-Dollar View

3 bd·2 ba
5· 7

$1,305.00 USD total for 3 nights

Oct 5 – 8, 2026

Explore near Winston-Salem

Cities and towns within driving distance of Winston-Salem, each bookable direct with the host.

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