Search Winston-Salem Cottages

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    one key illustration
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 105 Cottages in Winston-Salem with updated reviews, rates, and availability.

Cottage at Lake Jeanette - 2 min from Greensboro Science Center
Outdoor dining

Cottage at Lake Jeanette - 2 min from Greensboro Science Center

9.8 out of 10, Exceptional, (54)
"We were in town for our daughter's wedding. The house was perfectly located for us to attend "
Cottage at Lake Jeanette - 2 min from Greensboro Science Center
Cottage at Pilot Mountain
Outdoor dining

Cottage at Pilot Mountain

9.4 out of 10, Exceptional, (17)
"We enjoyed this property allot for a Christmas "
Cottage at Pilot Mountain
Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.

The price is $224
includes taxes & fees
$210 per night
May 19 - May 20
Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.
Quaint 2 bed 1 bath cottage style home
Exterior

Quaint 2 bed 1 bath cottage style home

9.2 out of 10, Wonderful, (33)
"It was a cozy spot to stay. "
The price is $209
includes taxes & fees
$185 per night
May 5 - May 6
Quaint 2 bed 1 bath cottage style home
★★NEW! 3 mins to HPU w/cornhole,throwing axes,billiards,firepit★★
Interior

★★NEW! 3 mins to HPU w/cornhole,throwing axes,billiards,firepit★★

10.0 out of 10, Exceptional, (23)
"Perfect spot for our family as we swung through for a visit at High Point! Owner communicated throughout our stay and was extremely helpful. Property was perfectly located and amenities were great. We’ll be back"
The price is $420
includes taxes & fees
$372 per night
May 28 - May 29
★★NEW! 3 mins to HPU w/cornhole,throwing axes,billiards,firepit★★
Lakefront Private Boat dock and ramp -Quiet-Large Screened in Porch-
Miscellaneous

Lakefront Private Boat dock and ramp -Quiet-Large Screened in Porch-

10.0 out of 10, Exceptional, (10)
"It was wonderful! The house is clean, cozy, and had everything we needed. The porch and dock were amazing!Tcovered porch is "
Lakefront Private Boat dock and ramp -Quiet-Large Screened in Porch-
Upscale City Cottage Getaway
Fridge, microwave, oven, stovetop

Upscale City Cottage Getaway

10.0 out of 10, Exceptional, (18)
"Close to campus and cozy space! "
Upscale City Cottage Getaway
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Towels, soap, toilet paper

1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

9.6 out of 10, Exceptional, (4)
"The property owners were very communicative and helpful. The property itself was beautiful and cozy—a perfect place for a weekend getaway. "
The price is $107
includes taxes & fees
$95 per night
May 5 - May 6
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Newly remodeled Lake Cottage with your own dock!
Property grounds

Newly remodeled Lake Cottage with your own dock!

9.8 out of 10, Exceptional, (32)
"Loved our weekend stay! Such a lovely place with plenty of space & everything we needed. Morning coffee on the porch with the views of the lake. Will definitely be back."
Newly remodeled Lake Cottage with your own dock!
Hikers Nest At Pilot Mountain
Terrace/patio

Hikers Nest At Pilot Mountain

9.6 out of 10, Exceptional, (8)
"Very clean and a great host. Nice location and quiet neighborhood. We would definitely stay here again. "
Hikers Nest At Pilot Mountain
Charming Yadkin Valley Cottage w/ Deck & Yard
Fridge, microwave, stovetop, dishwasher

Charming Yadkin Valley Cottage w/ Deck & Yard

10.0 out of 10, Exceptional, (40)
"5 star stay. "
Charming Yadkin Valley Cottage w/ Deck & Yard
Relaxing Cottage close to everything! Perfect for 2!Wi-Fi, Keurig,Outside space!
Property grounds

Relaxing Cottage close to everything! Perfect for 2!Wi-Fi, Keurig,Outside space!

10.0 out of 10, Exceptional, (52)
"Everything there was perfect. Only negative was a long trek from car to guest house (which was at the back of a very large backyard."
Relaxing Cottage close to everything! Perfect for 2!Wi-Fi, Keurig,Outside space!
Garden Cottage - Where Something is Always in Bloom.
Exterior

Garden Cottage - Where Something is Always in Bloom.

9.8 out of 10, Exceptional, (38)
"Great location between cities, lots of places to eat, easy to access."
The price is $203
includes taxes & fees
$180 per night
May 2 - May 3
Garden Cottage - Where Something is Always in Bloom.
Lakefront A-Frame Cottage with Kayaks & Fire Pit
Terrace/patio

Lakefront A-Frame Cottage with Kayaks & Fire Pit

10.0 out of 10, Exceptional, (17)
"Great little family vacay. Enjoyed firepit, dock, and our stay at the Lake It Easy A-frame lake house."
Lakefront A-Frame Cottage with Kayaks & Fire Pit
Relax, Rewind, Repeat New Country Cottage - Private, Rural Setting To Enjoy
Fridge, microwave, oven, stovetop

Relax, Rewind, Repeat New Country Cottage - Private, Rural Setting To Enjoy

10.0 out of 10, Exceptional, (48)
"Beautifully updated property that was very clean. "
The price is $441
includes taxes & fees
$412 per night
May 5 - May 6
Relax, Rewind, Repeat New Country Cottage - Private, Rural Setting To Enjoy
Cute cottage in a rural setting
Exterior

Cute cottage in a rural setting

7.4 out of 10, Good, (6)
"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."
The price is $299
includes taxes & fees
$279 per night
May 30 - May 31
Cute cottage in a rural setting
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
Terrace/patio

⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕

9.6 out of 10, Exceptional, (23)
"The house was great! Clean and fully stocked with everything we needed. Location is close to everything. Would definitely stay here again:)"
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
“The Shack” on Farmers Creek. Tree house Tiny house
Exterior

“The Shack” on Farmers Creek. Tree house Tiny house

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely gorgeous place to stay! Quiet and relaxing. "
“The Shack” on Farmers Creek. Tree house Tiny house
Foot Hill Farms II Hanging Rock
Terrace/patio

Foot Hill Farms II Hanging Rock

10.0 out of 10, Exceptional, (24)
"The home was perfect for our trip to Hanging Rock State Park. The owners paid every attention to detail and we had everything we needed. The Home was very clean and organized. Check in and out was a breeze and the owners were very accommodating. Thank you for the wonderful stay! "
Foot Hill Farms II Hanging Rock
Quiet Cottage - King Bed - Near wedding venue & Restaurants - Long Term Allowed
Fridge, microwave, oven, stovetop

Quiet Cottage - King Bed - Near wedding venue & Restaurants - Long Term Allowed

8.2 out of 10, Very Good, (14)
"Property was great - no issues Beds were all good. "
Quiet Cottage - King Bed - Near wedding venue & Restaurants - Long Term Allowed
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.
Don't see what you're looking for?
See all available properties in Winston-Salem
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winston-Salem

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Fridge, microwave, oven, stovetop

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

10.0 out of 10, Exceptional, (34)
"The house is super cozy, and the hot tub is amazing! We will definitely be coming back when we are in need of a staycation!"
The price is $238
includes taxes & fees
$211 per night
May 20 - May 21
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Towels, soap, toilet paper

1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed

9.6 out of 10, Exceptional, (4)
"The property owners were very communicative and helpful. The property itself was beautiful and cozy—a perfect place for a weekend getaway. "
The price is $107
includes taxes & fees
$95 per night
May 5 - May 6
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Cozy 1-bedroom condo in Downtown Winston-Salem
Private kitchen

Cozy 1-bedroom condo in Downtown Winston-Salem

10.0 out of 10, Exceptional, (1)
"Elizabeth is the most communicative and best host that I have ever rented from. I highly recommend renting any property that she has. "
The price is $259
includes taxes & fees
$229 per night
May 2 - May 3
Cozy 1-bedroom condo in Downtown Winston-Salem
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.