Family-friendly holiday rentals in Maryland

Mountain View Apartment

We offer a quiet and extremely clean place. We are only 6 miles from Belleayre Mtn Ski Center. Restaurants are nearby. You’ll love our place because of the neighborhood, the outdoors space, the light, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. WIFI is 300mbps. We have security cameras outside only, EV Charging station on the property. We now have an outdoor fire pit (wood not included). We also have a standby generator in case of a power failure.

Catskills Retreat: Hot Tub | Fireplace | Firepit

Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Bellwood Cottage 8-14min to all Roxbury Wed Venues

Bellwood Cottage is perfect for couples, families, or groups of friends looking to get away from it all in an private, idyllic setting. Great for all seasons and close to skiing (20-40 min from Plattekill, Belleayre, Hunter and Windham), hiking, fishing, swimming holes, restaurants and quaint towns. Walk to downtown Roxbury and Kirkside Park via the scenic rail trail. Close to all wedding venues - 4 miles to Roxbury Barn, 7 miles to Stone Tavern Farm, 4 miles to The Inn at West Settlement.

Modern Cabin w/Swimming, Boats, HOT TUB & VIEWS!

Welcoming you to the beautiful Catskills with our renovated (May 22') Modern Cabin with a Private SWIM POND situated on 6 acres w/ lovely and expansive mountain views and backed to 240 acres of NYC DEP LAND FOR HIKING, HUNTING & MORE!! The House is fully stocked to be enjoyed for all seasons! Take a dip, boat, fish or ice skate on the POND. Relax in the HOT TUB or lounge in the HAMMOCK or ADIRONDACK Chairs around the FIRE PIT while enjoying the views!! Enjoy grilling on the GAS GRILL!!

⭐A Secluded Schoolhouse Stay⭐

South Kortright Schoolhouse No. 5. A recently renovated, authentic former one-room schoolhouse located in the northern Catskill Mountains.This cozy space offers couples a romantic getaway and families a place to connect with the surrounding farmland. Schoolhouse No. 5 neighbors a working sheep farm with many fun activities available for guests. Visit the draft horses, chickens and turkeys, or help with daily chores. Bring your dog along for the journey, but please keep them leashed.

Catskill Cabin, Chill Apartment, 1st Fl * * * * *

Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-full life. We focus on healthy living, the environment & sustainability. Every day something in nature, a bear in the bushes, picturesque autumn foliage perfect for hipsters and dudes, kids and us grownups. Enjoy the mountain views. The Farmhouse is surrounded by miles of preserved forest land. Enjoy the mountain views. Parties or events are not allowed.

Hiking and Breweries! Mountain and river views!

RELAX, RELAX, RELAX - Located on one acre of land, the house built in 1917 sits above the Esopus river with direct views of the mountains and Esopus. It is only a 5-minute walk to great restaurants and shops in the village of Phoenicia or 5-minute drive to Phoenicia Diner & Woodstock Brewing. 20-minute drive to Hunter & Belleayre summer concerts and skiing. The house has upgraded high-speed internet (Spectrum Ultra 400 Mbps). Shankdaken STR # 22-STR-A0-029P

1st Class Rentals Munson Manor III at Murdock

**** Summer rental from June to August please use ONE guest for the pricing. Also check out time is 9 am *****From September to May please list the number of guests staying to get the proper pricing. We charge additional fees after 2 guests. Check out time is 11 am. *****We also have a $100 fee for a pet (dogs only) per stay. Location is awesome! This 5 bedroom, 2 bathroom home is located on a quiet street with several restaurants within walking distance.

Charming Catskills Victorian

Welcome to the absolutely charming and quiet Victorian village of Halcottsville, nestled in the Catskills Mountains. The house sleeps 6 and is great for families, couples, and groups. 10mn to Margaretville and Roxbury Villages. 10mn to Roxbury Barn and Estate, the Inn at West Settlement, and Stone Tavern Farm wedding venues. 15mn to Belleayre and Plattekill Ski Resorts. 40mn to Windham and Hunter Ski Resorts.