Vacation rentals in Portland

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Top-rated vacation rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view showcases a contemporary lake house nestled among trees, overlooking Lake Erie. The property features a light-colored roof and surrounded by lush greenery, with a private driveway leading to the home and nearby outdoor spaces.
Chalet in Brocton
4.93 out of 5 average rating, 240 reviews

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.

Top guest favorite
Cottage in Portland
4.96 out of 5 average rating, 136 reviews

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.

Top guest favorite
A private deck surrounds an elevated hot tub, providing a serene spot among the trees. The wooden deck features sturdy railings and offers a clear view of the surrounding forest, enhancing the natural ambiance of the treehouse setting.
Treehouse in Erie
4.99 out of 5 average rating, 155 reviews

Canopy Treehouse: Get-Away, Hot Tub, Casino, Lake

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.

Top guest favorite
Home in Dunkirk
4.95 out of 5 average rating, 150 reviews

Stay & Play

Welcome to your home away from home! Featuring complimentary WiFi, Roku TV, electric fireplace, pillow-top mattresses, games, snacks, fresh towels and toiletries, fully equipped Kitchen and complimentary coffee - you'll have all you need for your next get-away! You'll be walking distance to Lake Erie and a short drive to the beach, Chautauqua Lake or Niagara Falls! Your stay comes with an extensive list of local recommendations for places to eat, enjoy and entertain while you Stay & Play!

Guest favorite
The cottage features a modern design with large glass windows facing the lake. A picnic table is situated on the concrete patio, surrounded by a grassy area. Two kayaks are stored on the lawn beside the dock, which leads into the water.
Cottage in Cassadaga
4.95 out of 5 average rating, 141 reviews

Lakefront Sunset Getaway on Cassadaga Lake

Welcome to the Cottage! This cottage sits directly on Cassadaga Lake where you can enjoy beautiful sunsets every night from the concrete patio or from the couch. Feel free to go kayaking, fishing, or swimming directly from the dock or shoreline. Perfect for anyone who wants to enjoy lake life for the weekend, week, or month! *NEW* 2 kayaks are available for free use during your stay. No gatherings, events, and/or parties larger than your reservation. Free parking up to 2 cars.

Top guest favorite
A serene lakeside scene features a crackling fire pit surrounded by white Adirondack chairs. Soft lighting illuminates the area, reflecting off the water's surface under a twilight sky. The nearby cottage is visible, enhancing the peaceful atmosphere of the setting.
Cottage in Cassadaga
4.97 out of 5 average rating, 172 reviews

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!

Top guest favorite
Cabin in Sinclairville
4.93 out of 5 average rating, 274 reviews

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.

Top guest favorite
Apartment in Fredonia
4.94 out of 5 average rating, 481 reviews

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.

Top guest favorite
A red cottage with a steep roof is set beside a serene lake, surrounded by lush greenery. The water reflects the bright sky and distant trees. A wooden bench is positioned near the water's edge, offering a tranquil view of the landscape.
Island in Cassadaga
4.99 out of 5 average rating, 325 reviews

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.

Top guest favorite
Home in Westfield
4.99 out of 5 average rating, 642 reviews

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.

Guest favorite
Cottage in Westfield
4.81 out of 5 average rating, 103 reviews

The Cute and Cozy Cottage (On Lake Erie)

A bright and beautiful cottage lake house for you to enjoy. A short walk will take you to the lake where you can relax and enjoy the views. Plus, less than a mile down the road is the public Barcelona Beach, which also includes a marina and boat launch. You will be in the heart of wine country with 20+ wineries nearby.

Top guest favorite
A charming house is illuminated at night, showcasing its architectural features and lush landscaping. Soft lighting highlights the front porch and garden, while large trees provide shade around the property. The expansive yard is visible, creating a welcoming outdoor setting.
Apartment in Fredonia
4.95 out of 5 average rating, 136 reviews

Elegant 2 bedroom apt 1 block from SUNY Fredonia

Kick back and relax in this calm, stylish space—perfectly located in the heart of Fredonia. Just steps away from SUNY Fredonia, and a short drive to Lake Erie, local vineyards, Lily Dale, several scenic lakes, and the renowned Chautauqua Institution.

Popular amenities for Portland vacation rentals

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  2. United States
  3. New York
  4. Chautauqua County
  5. Portland