
Places to stay near Bailey Park
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Top-rated holiday rentals near Bailey Park
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Location! The Oasis at Camel City Lofts DT/WS/NC
☞ 200 Square foot covered deck overlooking city! ☞ Free Reserved Parking directly in front of apartment for 2 vehicles ☞ 300+ Mbps Wi-Fi ☞ One King Bed Studio with Kitchenette ✭✭✭✭✭ “Jeff, your place is perfect. Don’t change anything!” ☞ One block to Ramkat, Live Music Venue ☞ Self check-in ☞ Work Space with Desk, Office Chair and 40" monitor ☞ Air conditioning 》0.4 miles to Benton Convention Center, 8 min walk 》25 mins to Greensboro, Piedmont Triad Airport 》10 mins to Wake Forest University

House in Historic Sunnyside W-S
Absolutely NO Parties or LARGE GATHERINGS allowed!! You will be kicked out. If you are new to Airbnb/don’t have many ratings, chances are I will deny you if you aren’t clear on your trip details. Only registered guests are allowed to stay. You and your family will enjoy this spacious 3 bedroom home which is located in the historic Sunnyside area of town! Located a little over 1 mile into the downtown area, you will have easy access to nightlife, tourist attractions and lots of great food options

Luxurious, Historic 4BR Home in Downtown Winston
If you’re looking for a home with comfort and charm, this is the place for you! It has been renovated with the historic nature of the property in mind. There is an amazing amount of space for a big family or group of friends, with 4 bedrooms and 3 bathrooms. Luxurious furnishings and antique touches make you feel like you’re staying in an upscale hotel without the price- and with your own privacy. One of the best parts of this home is the location- walking-distance from downtown Winston Salem!

Cozy King Blue H2O Staycation , Pool & Hot Tub
Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

Salem Twin Deck
Conveniently located in downtown Winston-Salem, this well-maintained cottage built in 1900 includes a recently updated kitchen with island, wood floors, dining room, living room with full futon, washer/dryer, bedroom with queen, beautiful bathroom and walk-in shower. Easy walking distance to downtown restaurants, short drive to WFU main campus, Med School, WSSU and UNCSA. One off-street parking spot available. Self check-in only, but we live next door if you need anything or have questions.

K obscura
Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes gift card for coffee at Krankies. Note there is a train that passes by a few times a day and at night. We do allow pets but have a fee. Includes deep soaking tub, mini-kitchen and comfy king-size bed. Space is accessed via stairs. Parking included.

Luxury Downtown Loft
Enjoy a stylish experience at this centrally-located place. 3rd Floor urban loft in a secure, historic building in heart of downtown full of natural light, bright decor, and polished hardwood floors. Loft is just steps from Aperture theatre, 4th Street restaurants, the Stevens Center, and lots of shopping. Easy walk to everywhere downtown, and many ways to get to Wake quickly. Full of supplies and amenities - an oasis for business travel, vacation, or anything in between!

Old Salem Getaway - Visit DTWS via the Strollway
We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

West Salem Art Hotel, "Art"partment #1
Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.

The Red Door Cabin
Kick back and relax in this calm, stylish space! This little cabin is brand new and nestled just inside the woods, but only 1/2 mile from I-74 and only 10 min. to downtown Winston Salem, NC. This little cabin was built just for short term guests, it has granite tops, stained concrete floors, a beautiful tiled/stone shower, and will surely help you unwind and enjoy your stay in this delightful space!

Rocky Knoll Hideaway | Visit Family | Quiet Escape
Welcome to Rocky Knoll Hideaway — your peaceful home base for visiting family, relaxing, and recharging. Tucked among the trees, this cozy private cottage offers the perfect blend of quiet seclusion and convenient access to the area. Whether you’re here for a weekend visit, a holiday stay, or just a break from the busy pace of life, Rocky Knoll Hideaway offers a warm, welcoming place to land.

"Deacon House" 3 bedrooms
Looking for a place to stay in Winston Salem? Check out this 1,315 sqft. single family home that has 3 bedroom and 2 full bath. It has its own driveway with 2 car garage attached and fenced in backyard, guest occupy the entire house except the attic. It is just a few minutes away from downtown, Wake Forest University, Reynolda Garden, LJVM coliseum, Starbucks and grocery stores.
Popular amenities for holiday rentals near Bailey Park
Apartment rentals with wifi

Walker Loft 2 bed 2 bath! 1 mi to Coliseum, GAC

Downtown Underground Stylish Apt

Charming quiet condo all to yourself

Sanctuary – 1bedroom & 1bathroom

1 Bedroom Downtown near Tanger, Stadium, UNCG

The lovely 2 bedroom Greensboro Hideaway

Kit and Caboodle - Pleasing Condo for guests

The Windchase Condo
Family-friendly house rentals

West End Stained Glass on Sunset - 2 Bed/1 Bath

Tiny tiny house from 1930 near Wake

Beautiful 2 BR home with Office and Game Room

Modern Craftsman *Pet-Friendly* Near Downtown

Old Salem Restored Moravian Village 1700s

The Walnut Cottage. Charming! Near Everything!

Cozy Townhouse close to WFU!

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade
Apartment rentals with air conditioning

Lakeside Stay - Dog Friendly w/ Kitchenette

Horizons @ Summit - 2 Kings near Downtown Winston

Vintage Grocery-now Artsy downtown Apt near UNCSA

Ideal Downtown Getaway-walkable to everything!

The Clocktower Suite

The Joyful Loft Apartment! Private Studio Retreat

Cozy Apartment on Mini Farm!

Downtown loft with a view of Pilot Mtn
Other great holiday rentals near Bailey Park

Carriage House Downtown Winston

West End Charm

Premium Retreat close to WFU w/ Lvl 2 EV Charger

Cozy cottage in Ardmore, Pet friendly, fenced yard

The Man Cave

Historic stylish downtown condo, with free parking

Bright and refreshing apartment in Ardmore

Downtown West End Urban Oasis
Destinations to explore
- North Carolina Zoo
- Hanging Rock State Park
- Zootastic Park
- Pilot Mountain State Park
- Wet'n Wild Emerald Pointe Water Park
- Greensboro Science Center
- Stone Mountain State Park
- Lazy 5 Ranch
- Lake Norman State Park
- Wake Forest University
- Greensboro Coliseum Complex
- International Civil Rights Center & Museum
- Childress Vineyards
- University Of North Carolina At Greensboro
- Guilford Courthouse National Military Park
- Fairy Stone State Park
- Elon University
- Reynolda Village Shops & Restaurants
- North Carolina Transportation Museum
- Shelton Vineyards
- Andy Griffith Museum
- Martinsville Speedway
- Cherry Treesort
- Greensboro Arboretum





