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

A spacious living area features natural wood paneling and high ceilings, complemented by large windows allowing ample natural light. Red outdoor chairs sit around a wooden coffee table, while a cozy sofa invites relaxation. Views of the lake can be seen through the glass doors.

Chalet in Brocton

4.92 out of 5 average rating, 222 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

A covered porch extends from the front of the house, featuring wooden railings and a small set of steps leading down. Potted plants and lush greenery line the front, while a small table and chairs are set up for casual outdoor seating.

Cottage in Westfield

4.93 out of 5 average rating, 207 reviews

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

Guest favorite

An open floor plan features a queen bed with light bedding, complemented by a cozy couch and armchair. Large windows allow natural light to brighten the space, while wooden beams add character to the ceiling. A small coffee table and decorative plants enhance the inviting atmosphere.

Cabin in Portland

4.96 out of 5 average rating, 112 reviews

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.

Top guest favorite

Home in Cassadaga

5 out of 5 average rating, 105 reviews

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!

Guest favorite

A rustic, tiny cabin interior features a full-size bed adorned with a textured blanket and surrounded by wooden walls. A small side table with a plant and a wall-mounted decor piece adds character. Natural light enters through a nearby window, enhancing the cozy ambiance.

Cabin in Cassadaga

4.92 out of 5 average rating, 205 reviews

Angie's Country Stargazer Cabin shared hot tub acc

Close to lily dale ! Cannabis friendly Communal stay. Read whole listing b4 booking.nature is one of the greatest healers.rustic but can plug your own generator into cabin to power it. hot tub is shared and at hosts home. 1room tiny off the grid cabin ( heat provided labor day to memorial day) . Nice guest shower available at hosts home. hot breakfast in bed add on. This is our most private cabin . Own driveway. Get away from the busy world dogs welcome! Summer seasonal flush toilet

Guest favorite

A spacious bedroom features a comfortable bed covered with a light blanket. Two nightstands with lamps stand on either side of the bed. A large mirror reflects the natural light from the window. The wooden floor adds warmth to the neutral-toned room.

Home in Dunkirk

4.96 out of 5 average rating, 115 reviews

Stay & Play

Welcome to your home away from home! Featuring FREE 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!

Top guest favorite

A cozy cabin exterior is surrounded by trees, illuminated by string lights at dusk. A hammock is strung between two trees, offering a comfortable space to relax. Several chairs and a fire pit are visible, inviting outdoor gatherings.

Guesthouse in Forestville

4.99 out of 5 average rating, 189 reviews

Forestville Studio Cabin (Rural Guest Home)

Reconnect with nature at our secluded studio cabin on 5 acres, nestled beside a creek. Just 11 miles from Lake Erie and an hour from Niagara Falls. Only 528 yards to the snowmobile trail, 10 minutes to the Amish Trail, and 12 miles to Boutwell Hill State Forest. Enjoy hiking, biking, swimming, fishing, tubing, kayaking, skiing, snowmobiling, hunting, and exploring Amish country and local wineries. Located on a quiet dirt road, yet close to main travel routes.

Top guest favorite

A historical home is featured with a large, inviting porch framed by lush greenery and blooming flowers. The white railings and steps lead to the entrance, enhancing the welcoming ambiance of the property. Multiple windows allow natural light to brighten the exterior.

Apartment in Fredonia

4.95 out of 5 average rating, 450 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 calm waterway reflects a red cottage and trees, framed by vibrant green grass. An arched wooden bridge crosses over the water, leading to a deck with colorful chairs. The tranquil setting is enhanced by a slight mist rising from the surface.

Island in Cassadaga

4.99 out of 5 average rating, 318 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

A charming cabin is set in a wooded landscape, featuring a red metal roof and large glass doors that open to a deck area. Two Adirondack chairs surround a fire pit on a gravel base, inviting relaxation amidst nature.

Cabin in Russell

4.98 out of 5 average rating, 102 reviews

Secluded Egypt Hollow Cabin

Escape to a serene cabin near the Allegheny National Forest in Russell NWPA. Perfect for travelers and couples seeking a relaxing getaway surrounded by nature. 1 Bed. 1 Bath. Private Cabin Enjoy a stream, fire pit, and private driveway. Explore hiking, biking, and all types of boating nearby. Enjoy local businesses downtown Warren. Host available for questions and recommendations. Book your getaway now!

Guest favorite

A charming exterior of a renovated home displays a well-maintained garden with colorful flowers and a pathway leading to the entrance. An American flag is mounted on the side, framed by large windows that allow natural light into the living space.

Home in Westfield

4.99 out of 5 average rating, 605 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.