Holiday rentals in Shadyside

Suite Retreat

A Perfectly Imperfect Gem! Step into a slice of history with our charming upstairs apartment — she’s over 100 years old, full of stories, and aging gracefully. Think of her like your favorite old sweater: cozy, familiar, and full of character. This isn’t your cookie-cutter stay. Our suite is roomy, cozy, and safe — with a slanted hallway that adds just the right amount of personality! She may have a few blemishes, but don’t we all? What she lacks in polish, she makes up for in warmth and charm.

The Guest House on 8th - Apartment 2: Entire Apt

Cozy apartment in the heart of downtown Wheeling, within walking distance to restaurants and businesses. One block brings you to the scenic Heritage Walking Trail along the Ohio River. With easy access to I-70 it's the perfect stop-over if you're on your way through town, but if you're planning on a longer visit it's also a comfortable and convenient place to stay while visiting family or friends or just exploring our fun small town. We'd love to host you! Note: 2nd fl apartment w/ no elevator.

The Poplar One. Southern Hospitality in WV.

Only minutes away from Oglebay resort and waterfall, Wesbanco Arena, The Capital Theater, Centre Market and more, this quiet and cozy cottage is designed for you to come to and relax from your adventure. Located in the beautiful historic Woodsdale neighborhood, you will have access to a private garage with alley access and your cottage above. Feel free to stroll through the neighborhood sidewalks during the morning or evening or skip the traffic lights to see Oglebay's Festival of Lights!

Guesthouse on Genteel Ridge

Quiet, cozy cottage centrally located between Franciscan, Bethany, & West Liberty Universities! Two BRs boast one queen bed, one full, & a comfy sleeping couch in LR. Lots of natural light for reading, writing, & relaxing. Excellent restaurants within a 5 mile radius & many more slightly farther away! River access in downtown Wellsburg is just as close with plenty of nature trails and outdoor spaces in every direction! Star Lake Pavilion, Brooke Hills Park, and Oglebay within 1/2 hour.

Luxe Centre Market 3br Rowhouse

You won't find anything else like this in Wheeling! Located on an up-and-coming street in the eclectic, vibrant and very walkable Centre Market district. This exquisitely renovated rowhouse balances charm and character with swanky, modern, livable style. Walk to festivals, eateries, bars, wineries, shops, etc. Easy access to highways. Abundant free on-street parking. There's a fenced back yard which is shared with the adjoining rowhouse. Enjoy the firepit, the patio or relax on the deck.

Quiet Retreat in Friendly Village near Franciscan

Classic private loft suite with modern bathroom and parlor on the upper level of a beautiful Cape Cod house. Includes mini fridge, coffee maker, microwave, AC units and fireplace. In the Friendly Village of Wintersville, close to Franciscan University and highway 22. Short walk to shopping, restaurants and bus stop. Use of washer, dryer, and are kitchen available downstairs by appointment for additional fees. Games, books, baby gate, extra beds, bedding etc, are available on request.

The Owl's Perch Treehouse

Special Holiday Pricing! Reconnect and Rekindle This Holiday Season. Escape to The Owl's Perch at Owl Hollow, where the magic of the holidays comes alive. Cozy up amongst the glimmering Christmas lights and sip hot cocoa in the comfort of your arboreal abode. The Owl's Perch Treehouse offers a one-of-a-kind luxury escape. Combining rustic charm with refined comfort. Whether you’re seeking a peaceful getaway or a romantic retreat, the Owl's Perch invites you to relax and reconnect.

Dog-friendly Tinyhouse-Pond, Kayak, Grill, Firepit

Innisfree Farms' "Big Tiny" has full size comforts and a beautiful setting on our 70 acre farm. Get back to nature without giving up hot showers and A/C. The perfect countryside place to unplug (though TV and WiFi are available), cook out and relax by the fire. A combination of a rustic natural setting and your well-earned comforts. This tiny house has moved to a lakeside spot on our smaller pond -- AWD or 4WD vehicles will be needed in winter in the event of significant snow!

Grand By Design Farm Guest Suite

We love everything about our hillside home next to Grand Vue Park and enjoy how much our guest love it too. This space was designed with love and attention to detail. The extremely spacious suite with private entrance has a beautiful covered deck overlooking our hillside pasture and the wooded land behind us. An entire wall of windows offer perfect views. Many guest say the King size bed is most comfortable they have ever slept in . The bathroom is simply dreamy.

Secluded Tiny “Wild Mustard” Art/Spiritual Retreat

WE ARE ON WINTER BREAK - CLOSED UNTIL MARCH 2026. "The Wild Mustard"- Secluded off-grid tiny house in Wild, Wonderful, West Virginia. Beautiful views. Quiet, peaceful valley. 180 acres of private land and two miles of beautiful Buffalo Creek to enjoy. Queen bed in loft and a double futon. Extra guests may pitch a tent by the creek for $10/night/person. One of the most wish-listed properties in West Virginia! (see below). Pets welcome $35/pet - see pet policy.

The Gibson House!

The whole group will enjoy easy access to everything from this centrally located place. Wheeling casino, Ogelbay, Wheeling Park, 6 Golf Courses, and multiple restaurants are just a short drive away from this location. A few things are on the property. 1. Fishing poles are under the back porch. Feel free to use. 2. There is usually firewood on the side of the house. Feel free to use.

Cozy 1 bedroom apartment

Keep it simple at this peaceful and centrally-located apartment. Close to grocery stores and restaurants. Free off-street parking. Kitchen is stocked with coffee pot, toaster oven, microwave, hot plate and refrigerator. Bed linens and bath towels provided. Free WiFi. Furnished with one queen sized bed. Coin operated laundry available in building. We welcome out of town workers.