Holiday houses 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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Guest favourite
Treehouse in Erie
5 out of 5 average rating, 117 reviews

Jubilee Treehouse-Elevated Hot tub, Fireplace

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
Dome in Port Colborne
4.98 out of 5 average rating, 522 reviews

Luxury Romantic Glamping Dome near Niagara Falls

You'll love this unique and romantic escape for 2, located 30 minutes from Niagara Falls in Port Colborne. Our 400 sq ft geodome offers all the amenities needed for a relaxing, romantic getaway. Panoramic floor to ceiling window over looking a private pond with the opportunity to see wildlife from the comfort of inside the dome. Enjoy a fireplace, hot tub, comfy queen size bed, private deck with a fire table, outdoor shower, firepit on your own island, incinerating indoor toilet, AC, and wifi.

Top Guest favourite
Chalet in Brocton
4.92 out of 5 average rating, 225 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
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 favourite
Cabin in Portland
4.96 out of 5 average rating, 113 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.

Guest favourite
Cabin in Cassadaga
4.92 out of 5 average rating, 208 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

Top Guest favourite
Home in Dunkirk
4.96 out of 5 average rating, 123 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 favourite
Cottage in Cassadaga
4.96 out of 5 average rating, 137 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
Apartment in Fredonia
4.95 out of 5 average rating, 453 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
Island in Cassadaga
4.99 out of 5 average rating, 320 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
Cabin in Russell
4.98 out of 5 average rating, 106 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!

Top Guest favourite
Home in Westfield
4.99 out of 5 average rating, 610 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.

Popular amenities for Portland holiday rentals

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