Kid-friendly holiday rentals in Western Maryland

Family (& Remote Work) Friendly Cabin in the Woods

Renovated cabin with all the comforts, including a *new* screened porch with all-season heaters, large dining table, and porch swing. Bake a pizza in the wood fired oven while your kids jump on the in-ground trampoline or roast marshmallows. Enjoy hikes in and around the Dolly Sods; in the winter, ski, sled, or tube; in the summer, splash, boat, and raft on nearby rivers. Gas fireplace. WiFi, cable, smartTV, remote work set-up. Game cabinet, fort supplies, and special extras for all ages.

COZY CABIN in Alpine Lake Resort; 4 Season Getaway

Charming chalet-style cabin in a 4-season community for outdoor enthusiasts. Nestled in a quiet wooded area in the mountains of Alpine Lake Resort, WV. WiFi great for virtual work! Family/friends have plenty of room;4+ BRs, family rm, comfy loft, cathedral ceiling, game room, fire pit, spacious yard for group games. Walk 6 blocks to the Lake's beach, paddling, fishing, tennis, basketball & 1.5 mile to workout gym, indoor heat pool, golf, mini golf, XC ski. 19mi to DeepCreek Lake, WISP Ski & more

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

Don't be fooled by other misleading "slopeside" listings! This gorgeous 5-bedroom lodge is adjacent to Timberline's Winterset ski run — perfect for families. Outdoor hot tub. Large open floor plan, plus separate living area downstairs. Two gas fireplaces. Master suite has Jacuzzi for 2. Wifi, 2 flatscreen HDTVs. Please don't request to book this chalet unless you have at least 3 positive reviews on Airbnb. If you don't have 3 positive reviews, your request to book will be respectfully declined

Family Friendly Mountain Getaway; Theater & Arcade

This family friendly mountain retreat is the perfect vacation destination for all ages! Nestled into two private acres in Fern Mountain Estates, this house is located within minutes of Seven Springs, Hidden Valley and Ohiopyle. Between our arcade, movie theater room, and pool table, you’ll never hear the words “I’m bored” during your stay. Whether you are looking for a place to relax and unwind or explore the great outdoors, we think this place will be perfect for your stay. Adventure awaits!

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

Flint Hill Bright and Spacious Basement Apt, WiFi

This spacious and light-filled unit is perfect for touring Washington, DC with the whole family. It is the lower level, with separate entry, of a large family home. 25-30 minutes to downtown driving or by Metro. We are a short car/cab ride to the Vienna metro station. Many beds, a kitchenette, laundry machines, and a playset in the backyard for the littles. Street parking is by permit for up to one car. Put your feet up after trekking around; we’ve got board games and complimentary popcorn.

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Relaxing Getaway Near Shenandoah River Access

Come and enjoy our spacious 3bd/2ba home in Harpers Ferry, WV just across the Virginia state line and close to many local attractions! Perfect for families featuring a large fenced in backyard. Centrally located within 15 mins from historic Harpers Ferry; within 1/2 mile of public boat access to the Shenandoah River; 2 miles to Appalachian Trail; less than 15mins to numerous breweries & wineries; 10mins to Charles Town Casino. Enjoy all this wonderful area has to offer!

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!