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
4.93 out of 5 average rating, 233 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
The exterior of the farmhouse is captured, showcasing a two-story structure with a gabled roof and white siding. A wooden deck is visible, surrounded by manicured bushes and a rocky border. The green landscape extends into the distance under a clear blue sky.
Farm stay in Fredonia
4.99 out of 5 average rating, 142 reviews

Arkwright, Cozy Country Farm Stay!

Come and enjoy WNY winter sports!! We are ideally located for skiing, tubing and boarding directly between Peek N Peek (43 miles) or Holiday Valley (40 miles). There are snowmobile trail heads 5 miles from our location. Be in the country yet just 5 minutes from 4 local wineries and 10 minutes from dining/shopping. We have kept the farm house feel with plenty of room for a family or friends gathering. We hope you will visit our cozy country farm house location with 4 season fun, see our photos.

Top 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.
Cottage in Portland
4.97 out of 5 average rating, 127 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 clean camper is positioned on a grassy area, surrounded by lush green trees. Blue chairs are set near the camper, while a comfortable outdoor seating area is visible under an umbrella. A fire pit is present nearby, with a wood stack adding to the inviting outdoor space.
Camper/RV in Forestville
4.94 out of 5 average rating, 107 reviews

Camper in the country by area attractions dog ok

This is a very nice clean camper only minutes from the nys thruway , lake Erie Dunkirk ,Fredonia ,wineries and other area attractions. Fishermen welcome room for parking a boat. W/ stove ,,microwave,toilet, shower, coffee maker ,toaster ,pans,wi fi , tv gets 30 plus stations ,fridge / freezer, A.C. ,heat ,2 queen beds all linens included . A fire pit with firestarters and free wood also a bbq propane grill. Close to Lake Erie beaches and parks in Dunkirk,ny Small /med dog welcome.

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, 214 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

Top 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
4.95 out of 5 average rating, 143 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 two-story house is set against a backdrop of green trees and grass. The entrance features a set of front steps leading to a welcoming porch. Large windows are visible, allowing natural light to illuminate the space.
Home in Irving
4.97 out of 5 average rating, 149 reviews

Peaceful waterfront paradise

Take it easy at this remodelled, well stocked, peaceful, family friendly, vacation spot. Fish, swim, kayak, golf, visit wineries or just watch nature. Located in Sunset Bay, a beautiful sandy beach on Lake Erie, 10 minute walk away. This is a beach community, during the summer it is very active, two beach bars in the bay. There are boat launches nearby. Trains pass nearby, which may disturb your sleep. This area is 40-50 min. drive to the Buffalo/Niagara Falls area.

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
4.94 out of 5 average rating, 469 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, 323 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 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, 629 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.

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
4.96 out of 5 average rating, 117 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.

Top guest favorite
A single-story house is depicted with a light gray exterior and a brown shingled roof. A welcoming front porch features a small set of steps leading to a door. Lush green lawn surrounds the home, accented by trees with autumn leaves.
Home in Dunkirk
4.97 out of 5 average rating, 245 reviews

Cozy 2 BR 1 BA home in a nice quiet neighborhood

This cute little house is just down the road from SUNY Fredonia. It is just a 5 minute drive to the NYS Thruway, shopping, and restaurants. Downtown Fredonia and Lake Erie shoreline are a short drive away.

Popular amenities for Portland vacation rentals

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