Pinecrest Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 18 - Dec 19
Tomorrow
Dec 19 - Dec 20
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Pinecrest vacation 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 ￥16,276
￥41,718 total
includes taxes & fees
Dec 31 - Jan 1, 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 ￥14,276
￥30,191 total
includes taxes & fees
Dec 26 - Dec 27
3 mins from Downtown - PS5, King Bed & EV Charger
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 ￥13,389
￥38,963 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Downtown Charm, 3 Bdr, Near Rest and Bars
Outdoor dining
Jude's cozy & convenient downtown studio Apt.

Jude's cozy & convenient downtown studio Apt.

Jude's cozy & convenient downtown studio Apt.
High Point
9.2 out of 10, Wonderful, (11)
"Lovely place, host, and location in town!"
United States
Samir B.
The price is ￥7,620
￥16,483 total
includes taxes & fees
Dec 22 - Dec 23
Jude's cozy & convenient downtown studio Apt.
Fridge, microwave, oven, stovetop
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.
The price is ￥21,460
￥42,000 total
includes taxes & fees
Dec 21 - Dec 22
Vintage Modern Synthesis in the Heart of Winston-Salem
Fridge, microwave, oven, stovetop
Renovated Perfection in Quiet W-S Neighborhood

Renovated Perfection in Quiet W-S Neighborhood

Renovated Perfection in Quiet W-S Neighborhood
2.0 star property
Winston-Salem
9.8 out of 10, Exceptional, (176)
"All around great stay, very comfortable."
United States
Thomas M.
The price is ￥1,554,944
￥1,946,347 total
includes taxes & fees
Dec 19 - Dec 20
Renovated Perfection in Quiet W-S Neighborhood
Fridge, microwave, oven, stovetop
Spacious Townhouse In High Point Near HPU & Furniture Market

Spacious Townhouse In High Point Near HPU & Furniture Market

Spacious Townhouse In High Point Near HPU & Furniture Market
2.0 star property
High Point
9.0 out of 10, Wonderful, (10)
"Close to everything but in a quiet area. Highly recommend"
United States
Frederick W.
The price is ￥17,884
￥48,241 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious Townhouse In High Point Near HPU & Furniture Market
Fridge, microwave, oven, stovetop
Spacious 1king bd/2queen 15mins polar express

Spacious 1king bd/2queen 15mins polar express

Spacious 1king bd/2queen 15mins polar express
Lexington
7.8 out of 10, Good, (13)
"Had a good stay in the home."
United States
Duncan M.
The price is ￥15,183
￥36,572 total
includes taxes & fees
Dec 21 - Dec 22
Spacious 1king bd/2queen 15mins polar express
Fridge, microwave, oven, stovetop
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.
The price is ￥12,596
￥34,442 total
includes taxes & fees
Dec 30 - Dec 31
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
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 ￥17,953
￥40,751 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Quiet, newly renovated. Near everything!
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 ￥15,601
￥56,322 total
includes taxes & fees
Dec 21 - Dec 22
Arcade Kid Friendly Firepit Grill HotTub
2 bedrooms, in-room safe, iron/ironing board, free WiFi
Guest Favorite! Spacious Loft Overlooking NC Transportation Museum

Guest Favorite! Spacious Loft Overlooking NC Transportation Museum

Guest Favorite! Spacious Loft Overlooking NC Transportation Museum
Spencer
10.0 out of 10, Exceptional, (11)
"This place was a lovely retreat and the host was excellent. Overall, we had a wonderful experience."
United States
Amber F.
The price is ￥16,870
￥51,068 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Guest Favorite! Spacious Loft Overlooking NC Transportation Museum
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.
The price is ￥20,372
￥40,242 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Cozy 2-bedroom bungalow in lovely Winston-Salem
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 ￥13,389
￥39,910 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Chic 2BR/2BA Near Dining & Shops
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 ￥91,005
￥122,718 total
includes taxes & fees
Dec 26 - Dec 27
Heated Pool King Bed Jacuzzi Bath Arcade
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 ￥17,884
￥43,055 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming 2-bed, 2 full bath studio with WiFi, AC in Ardmore
Interior
Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo
Winston-Salem
7.6 out of 10, Good, (7)
"It was sufficient for our short term lodging needs."
United States
Stephanie
The price is ￥9,286
￥33,582 total
includes taxes & fees
Dec 23 - Dec 24
Quit, Cozy, Pet Friendly Condo
TV, stereo
Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.4 out of 10, Exceptional, (41)
"Not luxurious but perfectly adequate for three couples for three nights. A nice addition would be grab bars in both shower tubs for safety."
United States
Maggie B.
The price is ￥12,246
￥37,028 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Luxury 3BR Townhome - Sleep 6
Private kitchen
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem

Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem

Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
Winston-Salem
9.4 out of 10, Exceptional, (3)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveler
The price is ￥14,307
￥36,375 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
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 ￥13,528
￥45,093 total
includes taxes & fees
Dec 19 - Dec 20
Cute cottage in a rural setting
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pinecrest Hotel Reviews

Springhill Suites By Marriott High Point Downtown

Springhill Suites By Marriott High Point Downtown

10/10 Excellent
"The staff was great—especially the 3 am lady. The breakfast staff was very friendly. My only wish is that they had coffee all day. The rooms were very clean."
Christie 1-night trip
Posted 1 day ago
Springhill Suites By Marriott High Point Downtown

Find out more about Pinecrest

Search for holiday rentals in Pinecrest on Expedia! You can easily find your home rentals, villas, holiday apartments in Pinecrest using one of the methods below:

  • View our selection of featured holiday rentals in Pinecrest
  • Use the map to find apartments and other holiday homes in the Pinecrest neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pinecrest while they last

Look no further and take a look at our great range of rental properties in Pinecrest!

Frequently asked questions

Can I find a vacation rental in Pinecrest?

Yes, you can find vacation rentals near top attractions in Pinecrest, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Pinecrest?

BRAND NEW 4-bedroom 3-bathroom "Cottage on Conrad": This vacation home rental outside of Pinecrest is located in a rural location and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Pinecrest?

Explore the area and family-friendly sights such as North Carolina Transportation Museum, or get out into nature at a spot like Lake Thom-A-Lex Park. In the larger area, you’ll find Richard Childress Vineyards and Davidson County Historical Museum.

What’s a vacation rental in Pinecrest like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Pinecrest. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a small group gathering.