Vacation rentals in Chautauqua County

Hot Tub, Fire Pit, EV, Wine Tasting | Lux Cabins

"We enjoyed cooking in the cozy cabin, relaxing in the hot tub, and roasting marshmallows around the firepit, every moment was special" that's how a guest described their time at our cabins, tucked in the woods near Chautauqua Lake in Portland, New York. Kids take over the loft playroom while couples stargaze from the porch swing. Sleeps six across three private sleeping cabins connected to a shared amenity cabin with a full kitchen and two bathrooms. Wineries and hiking trails are minutes away.

Lake-View Cottage for 4 · Wine Tasting Included

Welcome to Fisherman’s Cottage; a cozy retreat with gorgeous lake views from the enclosed front porch and open-air back deck- perfect for catching a breathtaking sunset. Spend some time enjoying a complimentary wine tasting at nearby 21 Brix and return to comfortable furnishings, a fully equipped kitchen, and an efficient bath complete with a spa tub. Rent alone or pair with our newly renovated Mainstay cottage next door for extra space- ideal for families or groups seeking a peaceful getaway.

Modern Lakefront Cottage

Completely renovated, this lovingly designed, modern 2-bed, 2-bath, 1,000 sq. ft. cottage - filled with natural light - offers a cozy, elegant vacation and features an office with a very comfy pull-out memory-foam, queen couch-bed for the 3rd bedroom. (Extra Cleaning Fee of $100 when office converts to bedroom.) Located lakefront just 1 mile from Chautauqua Institution, the home has a dock & a boat slip just steps from the porch. Enjoy spectacular views downstairs and from the master bedroom.

Blue Oar/Luxe Lakehouse/Chautauqua

Welcome to Blue Oar Lakehouse on Cassadaga Lakes! Luxe 4 Bed / 3 full Bath, with stunning views, private dock, and 75 ft beach. Spacious and light-filled, renovated 1925 Craftsman home, perfect for family or group getaways. Located in a quiet, year-round neighborhood just minutes from Lily Dale and The Red House. Dog-friendly. Kayaks, paddle boards, pedal boat, bikes, yard games, grill, firepit on lakefront. If booked, check out our sister property, Blue Canoe (2BR/1BA, right on the water!

NEW! All Stowed In | Cozy Cottage on CHQ Water

All Stowed In! Some places you visit. This one you stow yourself into. A lovingly updated 1909 cottage tucked into the no-wake zone of Chautauqua Lake, with your own dock, boat lift, kayaks, fire pit and glassy-water mornings. Steps from the historic Stow Ferry and minutes from Bemus Point and Chautauqua Institution. Explore Southern Tier Brewing, wineries, foliage and hiking - or come when the snow flies for skiing, snowmobiling, ice fishing & cozy lake weekends. A 4 season destination.

Hidden Cove

Beautiful lakefront cottage on Findley Lake. Completely remodeled cozy one-bedroom cottage with two docks, 150 ft. of lake frontage, and boathouse. Tucked away on a quaint woodsy lot, you can enjoy breathtaking sunsets while relaxing around the firepit. Hidden Cove offers a one bedroom with a queen mattress and futon in the living room. The kitchen is fully stocked. Just a few miles from Peak n' Peek resort where you can enjoy skiing, cycling, ziplining, segway tours, and restaurants.

3 Bedroom Countryside Log Cottage Near Chautauqua

Three bedroom modernized log cottage 4 miles from Chautauqua Lake, 7 miles from Barcelona Harbor on Lake Erie. Room for fishing /snowmobile trailer on property, free boat launching at both lakes. Cabin is immediately adjacent to "Rails to Trails" for snowmobiling, cross country skiing and year around hiking. World famous Chautauqua Institution 10 min. Lily Dale "Spiritualist Capitol of the World" is 20 min. Chautauqua County's Largest Flea Market is 3 miles. Just to list a few.

Kingfisher Point: Beautiful New Lakeside Home

This stylish new lake house was completed in September of 2022, and we are excited to open it to visitors to the Cassadaga Lake. Our home on Cassadaga Lake rests among the trees of an old growth forest adjacent to protected wetlands. Guests can enjoy the sun setting over the lake each evening from one of two porches facing the lake, or from the kayaks that are available to guests. And yes, Kingfishers are frequent visitors to the lakes as well! (No smoking and no pets allowed).

Lakefront Log Cabin Retreat

The Lakefront Log Cabin is an authentic cabin on an expansive lakefront property featuring a large stocked pond. Entire property is very private. Natural beautiful wood throughout. You’ll think you’re in the Adirondacks. Open floor plan, stone fireplace, amazing 180 degree view of the Lake Erie and incredible sunsets. Wall of windows for views of lake from cabin. Huge patio overlooking the lake. Relax with the whole family at this peaceful place to stay.

Spacious Apartment in Historic Fredonia

This 2-bedroom, 1.5-bath apartment has a fully equipped kitchen; master suite with whirlpool tub; laundry, living, & dining rooms; & study. Attached to an historic home with on-site parking and private entrances, it has a porch overlooking a tree-shaded lot & quiet street. A 5-minute walk from SUNY Fredonia & downtown Fredonia, 3 miles from Lake Erie; a 35-minute drive from the Chautauqua Institute; & 1 hour from Niagara Falls, casinos, & ski resorts.

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.

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.