Holiday houses 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.

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.

Rustic Retreat

A newly renovated A Frame located in the rolling hills of the New York State countryside. Sleeps 4 adults comfortably with one queen futon on the first floor and one RV sized queen bed on the second floor. Includes a Hot tub, fire pit area looking out into the woods and a patio sectional on the porch. Air Conditioning is provided as well as internet, a smart tv, board games, and a small Nintendo 64 with preloaded games. A beautiful view of the woods and a large field, nature is sure to amaze.

Kelly Cottage

Comfort and convenience put you within walking distance to Barcelona Harbor and it’s historic lighthouse and centrally located on the Lake Erie Wine trail. Visit many art galleries and studios and attend various festivals throughout the year. For fishermen, opportunities include world class creeks for fly fishing and many charter boats for walleye excursions. Bring your bass boat, as we have plenty of parking. Chautauqua Institution is 15 minutes away. Guys or gals weekend groups welcome

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.

Captain's Treehouse: This Sunday! Beaches. Hot Tub

Experience the perfect blend of comfort and natural tranquility. Equipped with modern utilities, our unique treehouse creates an elevated space that is both luxurious and comfortable. The subtle rustic details create a warm, inviting space. Enjoy beautiful forest views from the private deck and stargaze while soaking in the elevated hot tub. Whether you prefer the comfort of an indoor hammock and swing, or the freedom of the outdoors, we’ve thoughtfully designed our spaces with you in mind.

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).

Blue Canoe/Upscale Lake Cottage/Chautauqua

Welcome to Blue Canoe Lake Cottage on Cassadaga Lakes! This small, 2 Queen Bedroom/1 Full Bath, newly renovated, open-concept, light-filled cottage offers 125 ft of private waterfront, a gated covered porch, & thoughtful details throughout. Enjoy 2 kayaks, 2 paddle boards, a pedal boat, 4 adult cruiser bikes, fire pit, & propane grill. Dog-friendly & perfect for up to 4 adults — luxury on the lake awaits! If booked, check out our sister property, Blue Oar (4BR/3BA, lakefront!

The A Frame-Cozy cabin, HOT TUB! Nature lovers!

Cabin with great amenities in the forest. There’s a creek flowing and a lovely pond. 4 seat Hot tub! Satellite Tv, WiFi, full size fridge, microwave, apartment size oven/stove, wood stove (primary heat in colder months) and electric baseboard heat 2 double beds, bunk beds. wood stove in garage. Easy access to NY State Land Snowmobile trails! Great location for hunters,Snowmobilers, cross country skiers, hikers, kayakers and all outdoor enthusiasts! Near Cassadaga Lake.

Quaint North East Cottage Near the Water

North East Cottage is a quaint, two level cottage nestled between 16 mile creek and Lake Erie. It offers two bedrooms, one pull-out couch with a queen mattress, two full baths and two large decks overlooking Lake Erie. The kitchen is fully stocked and newly remodeled! The living room provides warmth and coziness with a gas fireplace for cool evenings on the lake. A short walk down the road is a private beach for relaxing and spending the day on Lake Erie.

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.