Family-friendly holiday rentals in Milford

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.

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.

Western Catskills Paradise Four-Season Retreat

Serenity… Tranquility… Peace… slow down the pace and enjoy! What do you need? A Romantic getaway?... Family bonding time?... Painter’s paradise?... Writer’s retreat?... Spiritual or Youth Group retreat?... Large family reunion spot?... Home-Base camp for Youth baseball Tournaments at All-Star village or Dreams Park? Stay active or simply relax and do nothing. Time stands still and the rest of the world seems worlds away. So come make our home yours for a short stay or a long vacation.

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.

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 - Halcotsville, NY

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.

The Carriage House/Pine Hill Studio

Charming light-filled renovated 1200 SF carriage house in the lovely Catskills hamlet of Pine Hill. Two bedrooms with two additional daybeds in open loft-like space. Full kitchen and bath. Walk to Pine Hill Lake, hiking and restaurants and stores in town. Close to Phoenicia, Belleayre and Woodstock. Perfect for staying in the area for hiking, leaf peeping, weddings, and skiing ! Shandaken STR License #2023-STR-030