Search Winston-Salem Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 82 Cottages in Winston-Salem with updated reviews, rates, and availability.

Newly remodeled Lake Cottage with your own dock!
10.0 out of 10, Exceptional, (19)
"Lake house was clean, and beautifully decorated. We had a fun relaxing time fishing from the dock and drinking coffee on the porch in the rocking chairs. Added bonus was the electronic basketball game under the carport. The home was stocked with everything you needed and more! Would definitely stay there again."
Newly remodeled Lake Cottage with your own dock!
💎NEW!<2mins to HPU w/firepit,cornhole,billiards,throwing axes💎
10.0 out of 10, Exceptional, (6)
"House was clean, relaxing, had everything we needed. Didn't get enough time at the house to enjoy the backyard amenities. My husband and I were being celebrated by his family as we eloped back in September, 2024. High Point City Park is near and great for family gatherings."
The price is $127
$349 total
includes taxes & fees
Jun 5 - Jun 6
💎NEW!<2mins to HPU w/firepit,cornhole,billiards,throwing axes💎
Relax, Rewind, Repeat - New Country Cottage
10.0 out of 10, Exceptional, (27)
"The house was gorgeous in a very quiet neighborhood. Near a shopping center with a lots stores, fast foods and restaurants. Wall Mart around the corner. Spacious and clean. Loved the stay. I would stay in this home again."
The price is $235
$439 total
includes taxes & fees
Jun 2 - Jun 3
Relax, Rewind, Repeat - New Country Cottage
Save an average of 15% on thousands of hotels when you're signed in
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
9.8 out of 10, Exceptional, (17)
"My friend and I had the most wonderful stay at Casa Maria. So conveniently located, check out and in were so simple, and the fenced in yard were amazing! Would love to visit again"
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
Quaint 2 bed 1 bath cottage style home
9.4 out of 10, Exceptional, (18)
"Property owner had excellent communication right up to the time we walked in the door. The property was perfect. Clean, well stocked. Very quiet area. HIGHLY recommended."
The price is $114
$242 total
includes taxes & fees
Jun 16 - Jun 17
Quaint 2 bed 1 bath cottage style home
Cottage at Lake Jeanette - 2 min from Greensboro Science Center
9.8 out of 10, Exceptional, (35)
"The house was 1-3 minutes from all our activities. It was a great place to come rest and recharge. Hosts were attentive. We had plenty of towels for the weekend and the queen bed in the master was comfortable! Enjoyed drinking my coffee out on the patio in the morning and the kids cought fireflies at night. The neighbors were nice and even let us pet their dog. All in all a great stay!"
Cottage at Lake Jeanette - 2 min from Greensboro Science Center
Charming Family Getaway: Pet-Friendly Haven, very close to Wake!
8.0 out of 10, Very Good, (2)
"This house was everything it was described as and a perfect fit for our large group of 12!"
The price is $153
$431 total
includes taxes & fees
Jun 3 - Jun 4
Charming Family Getaway: Pet-Friendly Haven, very close to Wake!
Foot Hill Farms II Hanging Rock
10.0 out of 10, Exceptional, (14)
"We chose this area for how close it was to Hanging Rock. However, it rained very hard almost the whole time we were there. But the house was so comfortable that we really enjoyed just hanging out there. Very clean, with a lot of thoughtful details (spices, teas, coffee) and the sheets on the bed were so soft and amazing! The hosts were very easy to message and we always got a quick response. Would definitely go back!"
Foot Hill Farms II Hanging Rock
Lakefront A-Frame Cottage with Kayaks & Fire Pit
10.0 out of 10, Exceptional, (10)
"The house was adorable and Brad and Carolena were just the best hosts. We never had to guess how anything worked and the check-in and check-out process was flawless! The house itself was immaculate and welcoming, and the property was just beautiful. I can't say enough good things about the house, the lake, and our experience. I wish six stars was an option!"
The price is $151
$297 total
includes taxes & fees
Jun 2 - Jun 3
Lakefront A-Frame Cottage with Kayaks & Fire Pit
NEW! Waterfront - Private Dock - Firepit - Kayaks
10.0 out of 10, Exceptional, (9)
"My husband an i rented this beautiful home,for a relaxing getaway, an it was so much more my family had a great time. From.the fishing, kayaking, boating,an just enjoying the lake ,the views are so nice..the home had everything we needed,an more 😀"
NEW! Waterfront - Private Dock - Firepit - Kayaks
Cute cottage in a rural setting
8.0 out of 10, Very Good, (2)
"While there are other houses visible, this property was extremely quiet and relaxing. Great location, "civilization" easily accessible...just a short drive. Hope to stay again when we're more physically mobile (one broken back and one broken leg... hopefully we'll be fully recovered soon). Plenty of historic sites nearby."
The price is $99
$305 total
includes taxes & fees
Jun 7 - Jun 8
Cute cottage in a rural setting
Quiet Cottage - King Bed - Near wedding venue & Restaurants - Long Term Allowed
9.0 out of 10, Wonderful, (4)
"Clean and convenient for a weekend in town. Thanks!"
Quiet Cottage - King Bed - Near wedding venue & Restaurants - Long Term Allowed
Waterfront with Private Dock and HUGE Views
10.0 out of 10, Exceptional, (21)
"Beautiful house, great location, everything we needed to enjoy a weekend getaway."
Waterfront with Private Dock and HUGE Views
Cottage at Pilot Mountain
8.6 out of 10, Excellent, (4)
"Perfect place for the car show my husband and son went for. Parking area was perfect for car haulers, view was amazing."
Cottage at Pilot Mountain
⭐️Azaleas Cottage⭐️ 🐕🏟️📚🍔🏊‍♀️
9.8 out of 10, Exceptional, (9)
"House was super cute. Tiny but a perfect size for 3. We spent most of our time in family room and sun room. Had a good area to sit and snack or eat. We didn’t use any of the kitchen as we did not cook except to microwave a few items. Owner message me back immediately after I let him know I couldn’t find something. Maybe remove box springs on beds and go with just a slat bottom. Very squeaky. Not a ton of sink top space that made it tricky getting ready. Only issue but being a small older house...
⭐️Azaleas Cottage⭐️ 🐕🏟️📚🍔🏊‍♀️
The Violet House<br>Lovely Vintage Cottage
9.6 out of 10, Exceptional, (51)
"Cozy clean house with everything you need for stay."
The Violet House<br>Lovely Vintage Cottage
Mill House Cottage in rural setting, come visit!
10.0 out of 10, Exceptional, (5)
"The property is beautiful and conveniently located."
Mill House Cottage in rural setting, come visit!
Charming High Point Home w/ Yard: 4 Mi to Hpu!
3.0 star property
Charming High Point Home w/ Yard: 4 Mi to Hpu!
Greensboro Vacation Rental: 2 Mi to Downtown!
3.0 star property
Greensboro Vacation Rental: 2 Mi to Downtown!
Mid-Century Modern Cottage in Ardmore Area!
9.8 out of 10, Exceptional, (7)
"My family and I came up for my Residency. We really enjoyed our stay. The property was very clean and comfortable! We loved the whole layout. Very nice amenities!!"
Mid-Century Modern Cottage in Ardmore Area!
Don't see what you're looking for?
See all available properties in 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.

Other property types in Winston-Salem

High ceiling house close to downtown
4.0 out of 10, (1)
"The house was not in a good neighborhood. Major issues: Chained dog barked all night, the washing machine didn’t work, had to call to find the linens which were stored in a file cabinet in a bedroom, showed up during check in time and cleaning staff was still there, hardly any dishes on site so forget about cooking a meal there. Place was a disappointment at best, especially for the overall cost."
The price is $150
$271 total
includes taxes & fees
Jun 5 - Jun 6
High ceiling house close to downtown
Cozy Townhome in a Great Location
9.8 out of 10, Exceptional, (9)
"Great place for our Mother’s Day weekend"
Cozy Townhome in a Great Location
The Red Door Cabin
10.0 out of 10, Exceptional, (5)
"Serenity without isolation"
The Red Door Cabin
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.

Winston-Salem Cottages information

Number of reviews
257
Accommodation
82 Cottages
Lowest Price
$99
Highest Price
$235

Frequently asked questions

Why book your cottage in Winston-Salem with Expedia?
Booking a cottage in Winston-Salem is as easy as entering your travel dates and selecting an ideal place for a vacation in nature. From upscale retreats to low-cost properties and cottages that come with perks like free WiFi, Expedia has something for all tastes and styles. As for the best offers around? We have them too!
How can I find cheap cottages in Winston-Salem?
Expedia is here to help you easily track down cheap cottages in Winston-Salem. To discover a superb stay in a few quick clicks, simply use our handy filter tool to refine your search by budget, star rating and amenities.

Recent reviews of Winston-Salem hotels
Expedia verified reviews