
Holiday houses in Portland
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Top-rated holiday rentals in Portland
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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.

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.

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

Hallmark like cabin suite with panoramic view
Take it easy at this unique and tranquil getaway. Perfect for one or two Adults. Comfortable King Size Bed, private bath, kitchenette (not a kitchen) with airfryer/toaster oven, microwave and keurig. Take time away from the hustle and bustle and stay closer to nature in this lovely private suite. Linens, towels and numerous kitchen items provided. Plenty of popular activities and scenery in the surrounding towns and villages. Complimentary WIFI is available but can be unreliable.

Lovely 2 bedroom 1 bath country cottage on 5 acres
LOCATION LOCATION LOCATION... This cozy home is close to everything. Located just 2.5 miles from Chautauqua Lake, 10 miles from The Chautauqua Institution, 19 miles from skiing this is the perfect place. THE SPACE... First floor laundry, full kitchen, large screen tv featuring YouTube TV, gas grill and much more. Everything you need to feel at home. NOTE: THERE IS ROOM FOR 4 TO SLEEP, FEATURING TWO QUEEN BEDS AND A LARGE STANDARD (non pullout) COUCH TO SLEEP ON. NO GARAGE ACCESS

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!

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.

Lakefront Lake Erie Escape | Hot Tub, Sunset Views
Wake up to uninterrupted lake views and soak in the hot tub as the sun sets over Lake Erie. This direct lakefront getaway is ideal for couples, friends, or small families seeking a peaceful escape. Enjoy a private deck, stunning sunsets, pet-friendly, fast Wi-Fi for remote work, and a professionally cleaned, fully equipped home. Spring, summer, and fall weekends book quickly - limited availability during peak season. 📷 Check us out @door25stays

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.

Lily Dale Sanctuary! KING APARTMENT, We ❤️ Pets
Lily Dale Sanctuary! Private, Spacious, Pet-friendly Suite: KING bed, living room, bedroom w/en-suite bathroom. A/C, WiFi, Kayak, Bonus outdoor seating area. Asian-styled apartment on ground level of Victorian home w/incredible history. Susan B. Anthony stayed in this home when she visited Lily Dale. No stairs to climb! ** ONE PET MAXIMUM ** ***Guests must adhere to NY guidelines on COVID travel restrictions.***

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.

Lakefront Apt & boat slip, walk/boat/bike to Bemus
Lake Pines Loft private apartment was new in 2021. 1 Min. walk to private lakefront. Walk, or ride our included well-tuned classic bikes to Bemus. Take a quiet paddle in the canoe. Read, sunbathe, fish, or cocktail on a private dock, with mooring provided for your boat up to 25 ft. Private parking for 2 cars and a trailer.
Popular amenities for Portland holiday rentals
Other great holiday rentals in Portland

Bear Lake Lodge

The Blessing House (Sleeps 15+ (ask)

Tranquil Beach House Short Walk to Crystal Beach

Cozy Westside 3 bedroom upper apartment

Lakefront Getaway with Central AC

Cabin in the woods- close to trails

Barndominium 132

Brightside Cottage by Lake Erie
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Capital District, New York Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Holiday Valley Ski Resort
- Peek'n Peak Resort
- Waldameer & Water World
- Buffalo RiverWorks
- Allegany State Park
- Keybank Center
- Presque Isle State Park
- Midway State Park
- Highmark Stadium
- Kissing Bridge
- Turkey Point Provincial Park
- Buffalo Convention Center
- Frank Lloyd Wright's Martin House
- Splash Lagoon
- Eternal Flame Falls
- Canisius University
- Lucille Ball Desi Arnaz Museum
- Buffalo Zoo
- Holimont Ski Club
- Buffalo and Erie County Botanical Gardens
- Ellicottville Brewing Company
- National Comedy Center
- Chestnut Ridge Park
- Long Point Provincial Park




