Smoking friendly holiday rentals in Laurel Highlands

House 3bed Free Parking Walk to Bars & Shops

Have fun with the whole family & friends at our beautiful modern house. Located on a quiet street at one of the most vibrant neighborhoods in Pittsburgh South Side.Walking distance to bars & restaurants, grocery stores and coffee shops. Private fenced backyard perfect for families with kids. Free street parking available for our guests. Carnegie Mellon university, Pitt university, PNC Park and Heinz field 3 miles away from house. 3 bedrooms - king, queen and twin size beds, closets & bathrooms.

The Dave Cave

This unique 2 bedroom unit is an ideal place for cigar smokers and music lovers. The spacious apartment is decorated with a rock n' roll theme reflecting it's reputation as a popular live music venue (shows once every 2 weeks in the summer months). To access the 2nd bedroom you must go thru the master bedroom, so it's more of a bonus room for groups comfortable sharing spaces. Its located above the famous Leaning House Fine Cigars, established in 2006. We require a profile picture of your face.

Historic Eden Ranch, built 1837

Built in 1837, this three bedroom, 1 1/2 bath farmhouse sitting on 110 acres along Will Creek, the start of Wills Knob with Wills Mountain to the south was first transacted in 1728 when a Shawnee Indian known as "Will" sold 1000 acres to Benjamin Tomlinson for $30 and an old Rifle. This 110 acres was part of that 1000 acres! Farmhouse is registered in the Maryland Historic Society and has been restored to original floors from 1837 and original staircase and living room walls. Antique furniture.

Rustic Cabin on Cacapon River for Private Getaway

Rustic, 100+ year old primitive mountain cabin in West Virginia along the Cacapon River. Beautifully restored with wood stove, loft, & screened in porch. Access to 214 acres of private mountain land & over 1/4 mile of river frontage plus 1/2 acre pond, trails, and private shooting range. This cabin is 1-room and completely off grid. It has NO electricity or plumbing/running water, but does have a Porta-John serviced weekly. Renter will be cabin camping so pack accordingly; tents also welcome.

Hot tub | BBQ | Fire pit | Garage | Near Downtown

Minutes from Pittsburgh’s best: -3 min to Strip District -6 min to CMU & Pitt -7 min to Lawrenceville -9 min to Downtown (PPG Arena) -12 min to Northside (PNC Park) Unwind with these amenities: ✓ BBQ grill + hibachi setup ✓ Backyard fire pit for marshmallow roasting ✓ Bug-free outdoor dining tent ✓ Indoor jetted whirlpool hot tub for 2 ✓ Private bathroom — no sharing unless it’s your partner ✓ One-car parking garage, plenty other street parking Perfect if you want city access and privacy.

Dreamy Cottage: 2 bed w/fireplace, tons of charm

This family/pet friendly 2 bed/1.5 bath Dreamy Cottage, located in a lovely, quiet, family neighborhood in the center of Westmont is recently renovated and designer decorated in a boho-vintage-world-chic style. Step in become transported into a world of warmth, charm and comfort. You will find no other accommodation in the area with such extreme detail to design and comfort as this unique designer-owned home. There is a 25lb pet limit, 1 pet per visit acceptance at discretion of owner.

Firepit, view, hiking, hot tub @ mountain A-frame!

Come relax at Tiny Logs! Just 2 hours from DC or Baltimore, with hiking just steps away. Huge deck with hot tub, new Weber grill, dining table and chairs, rocking chair, and amazing views. Fast WiFi! Located in a private community with a lake, two docks, and a beach. Near spas, galleries, breweries, golf, historic sites, and more! 25 minutes to the historic town of Berkeley Springs, 35 minutes to Cacapon Resort State Park, 45 minutes to Antietam, & 60 minutes to Harpers Ferry.

Valley View Sunrise Site @TheGreat48Escape

Seeking peace, privacy and nature? The Sunrise Site delivery! This is a BYO tent campsite. This lovely slice of Laurel Highland heaven offers breath-giving views over Quecreek Valley. A mowed mile-plus trail provides a great place for a morning walk or an evening stroll through seasonal wildflowers. Great sunrises & stargazing . Gas, shops, eateries, Flight 93, Ligonier, Fallingwater, state parks, wineries, breweries, elephants! swimming holes, whitewater rafting nearby.

Nanny’s Rustic Retreat: Daisy Hide-A-Way

Nanny’s Rustic Retreat is a private, adults-only nature sanctuary designed for relaxation and freedom. Guests who appreciate a body-positive environment and natural outdoor living will feel at home. Discretion and respect are required.” Provided: 2 pillows, blanket and mattress cover & sheets/pillow cases for the full size bed in the cabin. There are two high chairs on the porch. All guests can enjoy the naturalist environment : hot tub/swimming pool area.

Luxury Glamping Yurt at River Mountain-Meadow View

Anything but ordinary in the best way! Luxury, style, and comfort in the great outdoors! River Mountain goes completely beyond your typical overnight with gorgeous accommodations in our glamping yurt tents, next-level guest service, modern amenities, and endless experiences in the outdoors. Family vacation, couples getaway, friends weekend -- River Mountain is a truly memorable getaway for all! SPECIAL UPDATE! - OUR HOT SPRINGS HOT TUBS ARE NOW OPEN!!

Tall Oaks Rustic Campsite

Tall Oaks Campsite is a small private site and is our only rustic style site, so no water or electricity, designed maximum 6 people with parking for 3 cars on site and space for 4 average size tents. This site has a single 8-foot picnic table, portable toilet, scenic overlook, hammock, fireplace, a bench and charcoal grill.

Pet-Friendly Home with Fenced Yard

Escape to a luxury 2-bed, 2.5-bath pet-friendly smart home in Pittsburgh for up to 6 guests. This private two-floor retreat features en-suite bathrooms, a gourmet kitchen, dedicated workspaces, and a fenced backyard with a BBQ. Perfect for families or remote workers seeking modern comfort just a short trip from downtown.