Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Cabin in Portland

Hot Tub, Fire Pit, EV, Wine Tasting | Lux Cabins

"We enjoyed cooking in the cozy cabin, relaxing in the hot tub, and roasting marshmallows around the firepit, every moment was special" that's how a guest described their time at our cabins, tucked in the woods near Chautauqua Lake in Portland, New York. Kids take over the loft playroom while couples stargaze from the porch swing. Sleeps six across three private sleeping cabins connected to a shared amenity cabin with a full kitchen and two bathrooms. Wineries and hiking trails are minutes away.

4.83 out of 5 average rating, 24 reviews

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

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.

4.96 out of 5 average rating, 156 reviews

Top guest favourite

The countryside home is illuminated against a night sky filled with stars, reflecting in the calm pond below. Warm light glows from the windows, surrounded by lush trees and peaceful natural surroundings.

Cabin in Westfield

Portage Ponds HOT TUB near Lake Erie-CHQ-Wineries

Escape into nature at our cozy, countryside home with amazing pond, woods and vineyard views. We're conveniently located between Chautauqua Lake & Lake Erie and close to the wine trail. -Less than 10 min to Barcelona harbor (Lake Erie) -Less than 10 min to CHQ Lake boat launch at Lakeside Park -10 min from Chautauqua Institution -5 min to quaint restaurants & shops in the Village of Westfield -Plenty of room for parking, including trailers -Hot tub -Space for everyone in your group! -Pets ok

4.97 out of 5 average rating, 105 reviews

Top guest favourite

A modern lake house is nestled among tall trees, featuring a spacious porch overlooking the water. The exterior combines dark siding with stone accents, and a small beach area is visible at the shoreline, complemented by a few outdoor chairs.

Home in Cassadaga

Kingfisher Point: Beautiful New Lakeside Home

This stylish new lake house was completed in September of 2022, and we are excited to open it to visitors to the Cassadaga Lake. Our home on Cassadaga Lake rests among the trees of an old growth forest adjacent to protected wetlands. Guests can enjoy the sun setting over the lake each evening from one of two porches facing the lake, or from the kayaks that are available to guests. And yes, Kingfishers are frequent visitors to the lakes as well! (No smoking and no pets allowed).

5.0 out of 5 average rating, 103 reviews

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

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!

4.97 out of 5 average rating, 193 reviews

Top guest favourite

A living area is characterized by natural wood beams and an open design. Two cushioned checkered chairs and a brown leather sofa with decorative pillows are arranged around a dark coffee table. Large windows allow for ample natural light.

Cabin in Westfield

Lakefront Log Cabin Retreat

The Lakefront Log Cabin is an authentic cabin on an expansive lakefront property featuring a large stocked pond. Entire property is very private. Natural beautiful wood throughout. You’ll think you’re in the Adirondacks. Open floor plan, stone fireplace, amazing 180 degree view of the Lake Erie and incredible sunsets. Wall of windows for views of lake from cabin. Huge patio overlooking the lake. Relax with the whole family at this peaceful place to stay.

4.96 out of 5 average rating, 101 reviews

Top guest favourite

A rustic cottage is nestled among trees, featuring a wooden exterior with a covered porch. The porch is adorned with seating and opens into the home through a white door. A small storage shed and a grill are visible beside the cottage.

Guest house in Westfield

Beachfront Cottage w/Amazing Views! Sunset Cottage

Come visit us at Steelhead Run offering panoramic views of the sunsets on Lake Erie. You will find this Two-bedroom cottage to be quite comfortable offering all the utility of a smaller home. When you arrive, you will find yourself nestled between Lake Erie and Chautauqua Creek on 7 forested acres with access to Lake Erie. On the beach you can spend time hunting for beach glass and driftwood, or take the half-mile walk along the beach to Barcelona Harbor.

4.99 out of 5 average rating, 119 reviews

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

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.

4.95 out of 5 average rating, 512 reviews

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

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.

4.98 out of 5 average rating, 354 reviews

Guest favourite

A spacious farmhouse with a light exterior is framed by greenery. A gravel driveway leads to the entrance, where a large porch is visible, adorned with chairs. Lush grass surrounds the property, and trees provide a natural backdrop.

Home in Brocton

VineCliff - Historic Farmhouse in Vineyard Setting

Escape to this historic 1800s farmhouse on 130 acres of vineyards, nestled along the Chautauqua County Wine Trail. This 3-bedroom, 1.5-bath retreat sleeps 6 and offers stunning serene views, private hiking trails, and easy access to wineries. Relax in cozy farmhouse charm, explore vineyards, or unwind in the woods. Perfect for wine lovers, nature seekers, and a peaceful getaway. Book your stay today!

4.9 out of 5 average rating, 58 reviews

Guest favourite

A spacious bed is positioned against a wall, adorned with decorative pillows and a patterned bedspread. Natural light filters through sheer curtains, creating a serene environment. Above the bed, a wall sign reads 'blessed beyond measure,' adding a personal touch to the room.

Home in Portland

The Blessing House (Sleeps 15+ (ask)

2021-Fully newly remodeled three story home. Clean, off street parking, fully loaded kitchen, washer and dryer, WiFi, Roku. Quiet home, about 20 min from Fredonia State, 20 min from Lake Erie Piers, 25 min from Chaut. Institute. About 1 hour- 1 1/2 hours to Niagra Falls. 45 min to Erie, PA

4.83 out of 5 average rating, 48 reviews

Top guest favourite

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.

Flat in Fredonia

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.

4.95 out of 5 average rating, 151 reviews