Holiday 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.

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

The Fisherman's Cottage - a Lakeside Loft

A cozy retreat in the heart of the Lake Erie Wine Trail that comes with a complimentary wine tasting. This newly renovated 1950's fishing cabin boasts modern amenities to ensure your comfort while retaining hints of it's former purpose. Wake up each morning to take in the panoramic view of Lake Erie from the back deck. Enjoy sunset from the screened in porch while you listen to the waves below. The Fisherman's Cottage is perfect for a girl's weekend at the wineries or a romantic getaway.

Blue Canoe/Upscale Lake Cottage/Chautauqua

Welcome to Blue Canoe Lake Cottage on Cassadaga Lakes! Brand new EVERYTHING!!! This upscale cottage oasis sits right on the waters edge with 125ft of private waterfront and a gated covered deck overlooking the lake. This incredible renovated space is light filled and very bright with lots of high-end details and amenities. Luxury on the Lake! 2 adult kayaks, 2 child kayak, 2 paddle boards, 4 cruiser bikes, pedal boat, fire pit, propane grill. Recommended for 4 Adults MAX. Dog Friendly!

Rock Cottage Getaway

Thinking of getting away from the city noise or just a quick weekend escape? Our beautiful Rock Cottage is the perfect fix! There's nothing like cozying up around the fire pit, getting the grill going and letting your worries go. Walking distance from downtown and the quaint coffee shops and eateries. Bike ride away from the historic Canadaway Creek(bikes provided). Short drive to some of WNY finest wineries. This Rock Cottage can also serve as your private getaway.

Lakefront Hosta Cabin

The Hosta Cabin sits on about 7 acres. We have 450' of lakefront with stairs that give access to Lake Erie. There are two cabins on the property. We live on the property as well. Each cabin has its own fire pit and chairs. While the cabins are next to each other, there is ample space between each. They are close enough if you want to make it a family stay and rent both. Please note, while we have a dog as part of our family, we do not allow guests to bring pets.

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.

Luxe Cabin/Hot Tub/EV Charger/Modern/Tranquil

Welcome to The Scandinavian Escape Tucked into the woods like a hidden gem, The Scandinavian Escape is your own private resort—where luxury meets warmth and modern comfort blends with natural beauty. Thoughtfully designed for relaxation, this peaceful retreat offers your group complete privacy, serene surroundings, and fun for all ages. **You will have the entire property exclusively to your group.**

Spacious Lake Front House

Our 1890 home is on Lake Erie and is roomy enough for the largest of families, but quiet enough for a romantic getaway for two. No beach access. Nearest beach access is next door at Lake Erie State Park. This is a country home on 3.3 acres of lake front property adjacent to a wooded, 355 acre New York State Park. You may encounter a spider, fly, ant, along with the abundant wildlife!