Family-friendly holiday rentals in Jamestown

Windsor Castle - Cozy Farmhouse Ellicottville

Windsor Castle - Your Cozy Ski & Golf Retreat Escape to serenity at Windsor Castle, a charming 2,300 sq ft farmhouse nestled on four rolling acres in Ellicottville. This beautifully restored 1900s home perfectly blends rustic charm with modern comfort, featuring a tranquil 3/4-acre pond that mirrors the changing seasons. Minutes from Western New York's premier ski destinations and golf courses, this private retreat offers the perfect balance of seclusion and accessibility.

Upstairs Loft on Main Street

In the midst of an Old-Order Amish settlement, stay upstairs in a modern loft with a queen-size bed, a double pull-out bed, full private bath, walk-in closet, dining area, and sitting room with access to a full kitchen on the first floor. Only a 2 1/2 hour drive to Niagara Falls, Pittsburgh, or Cleveland. Situated just up the street from downtown Spartansburg and Clear Lake, listen to the Amish buggies roll and experience real life in a small American town.

Chautauqua Lakehouse with a picturesque view

Tastefully decorated with lake charm. Minutes from Bemus Point and Downtown Jamestown. Across the lake from Lakewood and the new Chautauqua Harbor Hotel. A short drive to the Chautauqua Institute. Enjoy morning coffee and evening drinks on the front porch. Also a nice winter getaway. On the snowmobile trail. Holiday Valley Ski Resort -40 miles Peak &Peak Ski Resort - 30 miles Cockaigne Ski Resort - 18 miles Salamanca Casino - 35 miles

Island Cabin - The Paddle Inn

Abundant privacy is yours at this Island paradise on beautiful Cassadaga Lakes. Accessible by an arched bridge or boat, the cottage is brand new inside and out, is environmentally friendly, provides endless outdoor adventure and a charming interior. Fish from the back deck, swim in crystal clear lake water, relax on the covered porch, and enjoy boundless nature literally at your fingertips, in this very unique setting.

Apartment with AC, close to Ellicottville village

Beautiful, modern 2 bedroom/1 bathroom apartment perfect for a getaway with friends or a fun family weekend! **25% off for WEEKLY bookings** Equipped with all of the amenities of home including linens, kitchen wares, gas fireplace, washer and dryer and a TV in each room. Pull-out couch creates enough room for 6 people to stay. Located only 1 mile from the quaint Village of Ellicottville and 2 miles from the slopes!

Stay in style. Walk to everything!

Sure to be your favorite for visits to come! Enjoy this beautiful home with large kitchen, nice & comfortable furniture, and newer carpet throughout. Relax on the back deck or front porch. Off-street parking. WiFi. Go head-to-head on our air hockey or shuffleboard tables. Take a short walk to the heart of town! Perfect for time with spa weekends, golf outings, ski season, family, and more. Rentals are 30 days+.

Cozy apartment tucked into the forest (with sauna)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience including a sauna, you can home cook meals or barbecue on the deck, with nothing but forest beyond, relax and watch a movie on our LCD screen or use high speed Starlink internet.

CASA BELLA. Charming And Spacious.

CASA BELLA is a charming and spacious one bedroom, one bathroom space on the first floor of an unoccupied single family home in a quiet neighborhood. Located 1.7 miles from SUNY Fredonia, 8.1 miles from Lily Dale, 23 miles from Chautauqua and 69 miles from Niagara Falls. Perfect for families or a couple while visiting your college student, attending reunions, or local festivals.

Westfield Charmer

Charming 2 Bedroom/1 Bath home that has been totally remodeled. Brand new kitchen, appliances, floors, furniture, and more! Home has an open concept kitchen-living room, large bedrooms, huge deck with dining table and extra seating. There is an additional folding single bed if needed in MBR closet. Gas grill. Almost 1/2 acre backyard. Well behaved pets are welcome as are children.