Vacation rentals in Portland

The Sunset Hideaway

Great year round, natural wood, high beamed contemporary lake house. You’ll think you’re in Napa Valley. Natural beautiful wood throughout entire chalet style lake house. Open floor plan. Separate bunk house with heat/ac that has a queen trundle that sleeps 2 and two twin bunks. 100 feet exclusive Lake Erie frontage. Wood burning stove inside with large floor to ceiling windows for breathtaking views. Private lake and beach shared access next to property. Reliable high speed internet/Roku.

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.

Portage Ponds HOT TUB near Lake Erie-CHQ-Wineries

Escape into nature at our cozy, countryside home with amazing pond, woods and vineyard views. We're conveniently located between Chautauqua Lake & Lake Erie and close to the wine trail. -Less than 10 min to Barcelona harbor (Lake Erie) -Less than 10 min to CHQ Lake boat launch at Lakeside Park -10 min from Chautauqua Institution -5 min to quaint restaurants & shops in the Village of Westfield -Plenty of room for parking, including trailers -Hot tub -Space for everyone in your group! -Pets ok

Chautauqua Creek Retreat

Exhale, drive up the private driveway to the waterfront Chautaqua Creek Retreat on the coveted Chautauqua Gorge. Enjoy 4.4 wooded acres. Walk or drive down path to the creek. One of the best steelhead fishing in season and swimming holes in NY state. Use the fire pit, hike the creek, short walk to DT Westfield, visit wineries, antique shops, ski at peek n peek, Buffalo 1 hour, Niagara Falls 1 1/2 hour, 16 minutes to Chautauqua Institute. Newly renovated 3 bed 2.5 bath home. Dogs welcome.

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!

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).

Charming townhouse in Fredonia

Bring the whole family! Location & Comfort! Newly renovated, furnished & decorated townhouse-up to 8 guests w/ all the modern conveniences. This ideal location is only a 5 min drive from downtown Fredonia! Fully furnished w/ total of 3 bedrooms & 2 bathrooms. 1st floor: kitchen & dining, living room, full bathroom complete with washer/dryer, guest bedroom 1 (queen) , sunroom/patio with sleeper sofa 2nd floor: full bathroom, guest bedroom 2(full), guest bedroom3 (king)

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.

VineCliff - Historic Farmhouse in Vineyard Setting

Escape to this historic 1800s farmhouse on 130 acres of vineyards, nestled along the Chautauqua County Wine Trail. This 3-bedroom, 1.5-bath retreat sleeps 6 and offers stunning serene views, private hiking trails, and easy access to wineries. Relax in cozy farmhouse charm, explore vineyards, or unwind in the woods. Perfect for wine lovers, nature seekers, and a peaceful getaway. Book your stay today!

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.