Location

Dates

Guests

Vacation rentals in Winston Salem

Fully equipped kitchen

Spring in West Salem!

Large walk-in primary closet

Primary bedroom

Large open living space

Mid-Century Modern Charm in Downtown WS. Walk to food & bev

2 bedrooms·2 baths

Winston-Salem • North Carolina

5(19 reviews)

$715.00 USD total for 3 nights

Oct 22 – 25, 2026

Walk to Graylyn and Reynolda House

Walk to Graylyn and Reynolda House

Walk to Graylyn and Reynolda House

Walk to Graylyn and Reynolda House

Walk to Graylyn and Reynolda House

Walk to Graylyn and Reynolda House

5 bedrooms·3 baths

Winston-Salem • North Carolina

The Oak Crest

4 bedrooms·2 baths

Winston-Salem • North Carolina

5(29 reviews)

$914.82 USD total for 3 nights

Oct 20 – 23, 2026

The Brookwood

4 bedrooms·2 baths

Winston-Salem • North Carolina

5(249 reviews)

$886.23 USD total for 3 nights

Oct 24 – 27, 2026

The Double House at Brookwood

The Double House at Brookwood

The Double House at Brookwood

The Double House at Brookwood

The Double House at Brookwood

The Double House at Brookwood

8 bedrooms·4 baths

Winston-Salem • North Carolina

5(2 reviews)

$2,139.68 USD total for 3 nights

Oct 25 – 28, 2026

Luxurious Guesthouse in the heart of Winston-Salem

Luxurious Guesthouse in the heart of Winston-Salem

Luxurious Guesthouse in the heart of Winston-Salem

Luxurious Guesthouse in the heart of Winston-Salem

Luxurious Guesthouse in the heart of Winston-Salem

Luxurious Guesthouse in the heart of Winston-Salem

1 bedroom·1 bath

Winston-Salem • North Carolina

5(13 reviews)

$372.00 USD total for 3 nights

Oct 19 – 22, 2026

The Polo

4 bedrooms·2 baths

Winston-Salem • North Carolina

5(189 reviews)

$987.82 USD total for 3 nights

Oct 25 – 28, 2026

The Cottage

2 bedrooms·2 baths

Winston-Salem • North Carolina

5(146 reviews)

$870.75 USD total for 3 nights

Oct 25 – 28, 2026

The Idlewilde

4 bedrooms·3 baths

Winston-Salem • North Carolina

5(150 reviews)

$634.24 USD total for 3 nights

Oct 19 – 22, 2026

Double House - Sleeps 16 Walking Distance to WFU

Double House - Sleeps 16 Walking Distance to WFU

The Front House: 4 Bedrooms, plenty of room for 10 people!

Double House - Sleeps 16 Walking Distance to WFU

Double House - Sleeps 16 Walking Distance to WFU

Double House - Sleeps 16 Walking Distance to WFU

6 bedrooms·5 baths

Winston-Salem • North Carolina

5(39 reviews)

$2,034.54 USD total for 3 nights

Oct 25 – 28, 2026

Charming front exterior w/ classic curb appeal, inviting porch, & a warm welcome from the moment you arrive.

Bright, welcoming living room w/ comfy seating, playful pops of color, & an easy flow for relaxing or gathering together.

Sunlit dining nook w/ cheerful accents, cozy seating, & windows that make every meal feel light and unhurried.

Calm bedroom retreat w/ soft tones, layered textures, & a peaceful vibe for winding down after full days out.

Spacious living area w/ plush sofas, warm decor, & plenty of room to lounge, stream, or spend time together.

Hygge High Point

2 bedrooms·2 baths

High Point • North Carolina

$1,395.46 USD total for 4 nights

Oct 20 – 24, 2026

Spacious 4BR Home w/ Game Room and Backyard Oasis image 1

Spacious 4BR Home w/ Game Room and Backyard Oasis image 2

Spacious 4BR Home w/ Game Room and Backyard Oasis image 3

Spacious 4BR Home w/ Game Room and Backyard Oasis image 4

enjoy our peaceful backyard oasis

Spacious 4BR Home w/ Game Room and Backyard Oasis

4 bedrooms·2 baths

Greensboro • North Carolina

5(37 reviews)

$1,040.00 USD total for 3 nights

Oct 19 – 22, 2026

Downtown retreat- Pilot Mt. Views- sleeps 8 image 2

Downtown retreat- Pilot Mt. Views- sleeps 8 image 1

Downtown retreat- Pilot Mt. Views- sleeps 8 image 3

Downtown retreat- Pilot Mt. Views- sleeps 8 image 4

Downtown retreat- Pilot Mt. Views- sleeps 8 image 5

Downtown retreat- Pilot Mt. Views- sleeps 8

3 bedrooms·2 baths

Pilot Mountain • North Carolina

4.83(6 reviews)

$725.00 USD $665.00 USD total for 3 nights

Oct 19 – 22, 2026

Spacious 3BR/2.5BA Townhome in the Heart of GSO

Spacious 3BR/2.5BA Townhome in the Heart of GSO

Spacious 3BR/2.5BA Townhome in the Heart of GSO

Spacious 3BR/2.5BA Townhome in the Heart of GSO

Spacious 3BR/2.5BA Townhome in the Heart of GSO

Spacious 3BR/2.5BA Townhome in the Heart of GSO

3 bedrooms·2 baths

Greensboro • North Carolina

$1,390.73 USD total for 3 nights

Dec 31, 2026 – Jan 3, 2027