Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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

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Top guest favourite
A hot tub is positioned on a wooden deck, surrounded by lush trees. The structure features wooden accents and a sloped roof, with a walkway leading to additional outdoor seating. Natural light filters through the canopy, creating a serene atmosphere.
Treehouse in Erie
5 out of 5 average rating, 152 reviews

Treehouse-Jubilee: Get Away- Tonight! Hot Tub

There is something special about being up in the trees, surrounded by nature. In this cozy, little treehouse, you will find that no detail has been overlooked. Enjoy the forest view where it’s likely you'll see wild deer or turkey. Build a fire in the fire pit, have a stargazing soak in the hot tub, enjoy the freedom of an outdoor shower (available May 1- Oct 25), or relax on the hammock deck. You’ll have everything you need for the perfect getaway. Once you arrive, you won't ever want to leave.

Top guest favourite
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, 236 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 favourite
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, 131 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 favourite
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 favourite
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, 148 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!

Top guest favourite
A serene lakeside view showcases the cottage positioned on a rocky shoreline. Two white Adirondack chairs are placed near the water, complemented by a small firepit surrounded by soft landscaping. Bright blue skies and calm water create a peaceful atmosphere.
Cottage in Cassadaga
4.97 out of 5 average rating, 167 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 favourite
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.
Guest house in Forestville
5 out of 5 average rating, 203 reviews

Forestville Studio Cabin (Rural Guest Home)

Reconnect with nature at our guest 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 favourite
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.
Flat in Fredonia
4.94 out of 5 average rating, 477 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 favourite
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 favourite
A landscaped exterior showcases vibrant flower beds in a variety of colors, bordered by well-maintained greenery. The view extends to Lake Erie, with calm waters reflecting the sky. A spacious deck is visible in the background, providing an area for relaxation and enjoying the scenery.
Home in North East
4.96 out of 5 average rating, 127 reviews

Lakefront Escape

Our home is located in historic North East Pa. The house sits on a bluff overlooking beautiful Lake Erie with steps to access the beach. We have 2 bikes, a fire pit and plenty of seating on the oversized deck to enjoy your view of bald eagles flying along the shore. A split air system gives Air conditioning in the entire home makes your stay very comfortable. We are certain you will love your escape to the lake.

Top guest favourite
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, 637 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 favourite
A light-filled living area showcases large windows with lake views. A cozy, elegant loveseat and two tufted armchairs frame a wooden coffee table, positioned on a soft area rug. A potted plant adds a touch of greenery near the open door leading to the outdoor space.
Home in Jamestown
4.99 out of 5 average rating, 135 reviews

Cozy Lakefront Cottage

Enjoy and relax with the whole family at this peaceful place to stay. The Chautauqua lake is just a few steps from the backyard. Enjoy fishing, (ice fishing in the winter!) boating, bonfire, bbq, canoeing and breathtaking sunsets are not to be missed! This home is newly renovated and is located near all major shops and amenities. Free parking.

Popular amenities for Portland holiday rentals

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