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Places to stay near Chester Bowl Ski Resort

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Top-rated vacation rentals near Chester Bowl Ski Resort

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The Griffin riverboat is docked under a colorful rainbow, with its name prominently displayed on the side. Surrounded by lush greenery, the scene is illuminated by the warm light of sunset reflecting off the water's surface.

Houseboat in Superior

4.97 out of 5 average rating, 119 reviews

Griffin - The Lake Superior Riverboat

Channel your inner Mark Twain. Read, rock, and relax on the water, at the foot of a retired Northern Pacific Ore dock. The Griffin is a functioning riverboat, driven by paddle wheels, originally modeled after historic Mississippi steamboats. It is located at a mom and pop boat yard, which is quite different from a fancy marina. Work happens here. Metal is welded here. Engines are torn apart and put back together here. Friends become family here. Come and become a part of the Griffin’s story.

The front entrance of the Brewtel building features large glass block windows flanking a central glass door. The word 'BREWTEL' is displayed on the wall beside the entrance. A decorative planter with white flowers adds a touch of greenery to the exterior. A well-maintained lawn with gravel borders the pathway.

Apartment in Duluth

4.92 out of 5 average rating, 249 reviews

Lake Superior Brewing Brewtel 2 Bedroom Apartment

Newly rebuilt in a historic brick building, this charming 1000 square foot apartment is spacious, comfortable and so unique. This apartment sleeps 5+, with king and queen bedrooms, and a comfortable queen sofa bed. Polished original concrete floors, high ceilings, luxury terrazzo tiled walk in shower, reclaimed Victorian era oak throughout make this apartments so special. Steps from Duluth’s Lakewalk and located near Lester River Park, Brighton Beach, the North Shore and Lake Superior Brewing!

Top guest favorite

The exterior of the early 20th century home is showcased, featuring a welcoming entry with a red door and white columns. Lush green lawns and vibrant flower beds surround the house, while large windows allow natural light to fill the interior spaces.

4.95 out of 5 average rating, 321 reviews

Arrowhead Garden Retreat

No matter the season, you'll enjoy my early 20th century home in Duluth, five minutes from both the University of Minnesota-Duluth Campus and The College of St. Scholastica. In summer you'll enjoy the private patio surrounded by gardens. On cool fall nights you'll want to gather by the fire-pit. In winter, you'll escape the snow in the warm living room lit by the fire-place. In all seasons, you'll gather in the fully updated white granite kitchen to cook and share stories of your day.

Top guest favorite

A jetted tub is positioned in a wooden alcove, surrounded by beige tiles. Two towels hang above the tub, and a basket containing toiletries is placed nearby. Soft lighting highlights the tub's gentle curves, creating a relaxing atmosphere.

Apartment in Superior

4.96 out of 5 average rating, 138 reviews

Sweet Jacuzzi Suite

Whether you're in the Twin Ports for work or play, our little getaway is the perfect place to unwind. (Let us know if you're bringing the kids! ❤️) Fix up a snack in the kitchenette or relax on the full-size futon. After that, settle into a comfy queen-sized bed after a luxurious soak in the jetted tub! Amble down to nearby, kid-friendly Billings Park, or we're just a short drive away from anything in Superior or Duluth, including shopping, the arts, and our gorgeous Lake Superior!

Top guest favorite

The exterior of the storage container unit is showcased in a serene setting, featuring large windows and a sleek black facade. The surrounding area is landscaped with grass and bordered by a stone path, under a sky painted with soft hues of sunset.

Shipping container in South Range

4.98 out of 5 average rating, 150 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

Top guest favorite

A private entryway is highlighted by a set of stairs leading to the main apartment. Two bright red adirondack chairs are arranged around a circular fire pit on a grassy area, creating a cozy outdoor seating space.

Guest suite in Duluth

4.97 out of 5 average rating, 709 reviews

Private Lake View Hike/Bike Trail Access 1 Bedroom

View epic sunrises & sparkly city lights perched near the top of the city! Great Duluth Harbor view. You will sleep sound with a top reviewed Tuft & Needle mattress with premium bedding & pillows. Join your friends on the Duluth Traverse hike, snowshoe & bike trail just 100 yards away. You will be a few blocks from the hip Lincoln Park Craft District, Canal Park, and Downtown. New to Duluth? Message us for our recently updated Guidebook! License: 760178. Permit: PLASH1904001

The exterior of a single-story home is surrounded by mature trees and greenery. A spacious parking area is visible in front, with a white fence providing privacy. Sunlight illuminates the scene, highlighting the charming façade of the house.

Home in Superior

4.91 out of 5 average rating, 550 reviews

★ Mid Century Modern!★7 miles to Canal Park★

LICENSE- FACILITY ID #TBES-AW7P46, Approved - Douglas County Health Inspection. This retro house will host your Twin Ports experience. Kitchen amenities provided are cookware, dishes, glasses, silverware, coffee, tea, granola bars, and filtered water. Kitchen appliances include dishwasher, oven, stove, refrigerator, microwave, coffee pot, and toaster. Bathroom linen, toilet paper, shampoo, conditioner, body wash, and hand soap are all provided. Parking off the street - 2 spots.

A cozy bedroom features a spacious bed with a grey bedspread, flanked by two bedside lamps. A light fixture hangs above, and a large window allows natural light to illuminate the maple hardwood floors. A mirror reflects the room's design elements.

4.96 out of 5 average rating, 142 reviews

Nola’s Nest - North Coast Vintage House

Wonderful lake view from back deck, very short walk to Lake Superior! Sorry, no pets! This quiet, low-key neighborhood is tucked down near Lake Superior in Duluth's Endion neighborhood. The house itself was built in 1890 and features a lake view from the patio, claw foot tub, radiators, MCM pieces and modern vintage charm. It's a 3 walk block to the lake walk where you can pick agates and watch the waves on beautiful Lake Superior.

The entrance features a colorful door adorned with vibrant accents and a welcoming sign above. Lush plants and flowers frame the porch, which is enclosed by wooden railings. A stone pathway leads to the door, enhancing the inviting appearance of the home.

4.91 out of 5 average rating, 149 reviews

SUMMERHILL, a cheerful house

With a view of Lake Superior and Duluth's harbor, SUMMERHILL is full of color and light. 5-blocks straight up from downtown and Canal Park. Park on the street right in front of the house, or park off-street in the alley behind the house. On city bus routes. Safe and friendly, this is a quiet house and probably not a good fit for people who want a livelier, party atmosphere. The owner, a senior citizen, resides in an adjacent apartment.

Aerial view of House on the Hill Duluth, surrounded by lush greenery. The spacious home features a light brown exterior and large windows, showcasing expansive vistas of Lake Superior and the Duluth Lift Bridge. The vibrant cityscape is visible in the background.

5 out of 5 average rating, 100 reviews

House on the Hill Duluth-Epic Lake Superior Views

Welcome to House on the Hill Duluth! This incredible home offers some of the best views of Lake Superior, the Duluth Lift Bridge and the greater downtown right from the comfort of your own private deck or cozy sofa indoors. This spacious, 5-bedroom 5-bathroom home, complete with full master kitchen and multiple gathering spaces, is the perfect place for friends and family to come together. Duluth Rental Permit Number PL 21-166

A bright living area features large windows that allow natural light to fill the space. A comfortable sofa faces a modern fireplace framed by built-in shelves. A round dining table sits alongside a small seating area, with decorative elements enhancing the serene ambiance.

Apartment in Duluth

4.91 out of 5 average rating, 148 reviews

New London Loft

This newly renovated 3-bedroom apartment is located in the neighborhood of Lakeside, right on Duluth's Lakewalk. The space offers plenty of room for groups while being cozy enough for a couple's getaway, with a serene aesthetic inspired by Duluth's natural beauty and adventurous spirit. Let New London Loft be your home base for adventure in the North. Please note, apartment is a 2nd floor walk-up.

Top guest favorite

A scenic outdoor dining space features a round table set with colorful dishes and a vase of fresh flowers. Nearby, trees provide shade, while a view of the calm water and distant shoreline enhances the tranquil atmosphere. A boat dock is visible in the background.

4.97 out of 5 average rating, 119 reviews

Park Point Retreat | Steps from Beach & Canal Park

Welcome to Bayview Cottage, your year-round lakeside getaway nestled on Duluth’s iconic Park Point. This charming, 5-star-rated home sits on five spacious city lots with Superior Bay in the backyard and Lake Superior just steps away. It’s the perfect blend of rustic Northwoods charm and modern comfort—ideal for families, couples, and groups looking to unwind, explore, and make lasting memories.

Popular amenities for vacation rentals near Chester Bowl Ski Resort

Free parking on premises

Air conditioning

Condo rentals with wifi

A bright living area features a comfortable gray sofa complemented by a round area rug. A wooden coffee table sits in front of a TV mounted on the wall. Natural light streams through a large bay window, enhancing the welcoming atmosphere.

Condo in Ashland

4.9 out of 5 average rating, 117 reviews

Main Street apt 2 blocks from Lake Superior!

A spacious kitchen is highlighted by wooden cabinetry and a striking brick wall. Countertops are topped with various kitchen appliances, including a coffee maker and utensils. Lighting is provided by overhead fixtures, and the room features a warm, inviting design with a view of the adjacent dining space.

Condo in Two Harbors

4.88 out of 5 average rating, 128 reviews

The Fireside at Silver Creek B&B w/ SAUNA

A spacious living room is showcased with a large area rug covering the floor. A seating arrangement includes a futon and a table, and a flat-screen television is mounted on the wall. Natural light filters in through the windows, leading to a private balcony.

Condo in Bayfield

4.75 out of 5 average rating, 173 reviews

Superior Hideaway

A spacious dining area features a large wooden table surrounded by white chairs. Open shelves display decorative items, while a modern light fixture hangs above. The adjacent kitchen is visible, showcasing cabinetry and the entrance door, with natural light illuminating the space.

Condo in Duluth

4.9 out of 5 average rating, 72 reviews

Lake & Lift Bridge Views | Top Floor | Large Deck

A cozy studio condo features a spacious bed with dark bedding, subtly accompanied by decorative throw pillows. Natural light filters through two windows near the entrance, illuminating the room. A rug lies at the door, adding warmth to the entryway.

Condo in Bayfield

4.78 out of 5 average rating, 161 reviews

One Minute Walk to Lake Superior. Brookside #10

A cozy living area features a grey sofa with accent pillows, two blue chairs, and a red coffee table. Large windows provide unobstructed views of Lake Superior, while natural light brightens the space. Decorative artwork and a stylish lamp complete the welcoming atmosphere.

Condo in Duluth

4.77 out of 5 average rating, 65 reviews

Luxury One Bedroom Condo on Lake Superior

A spacious living area features large windows offering panoramic views of the lake and downtown Duluth. A comfortable sofa faces a flat-screen television, while a wooden coffee table is centered on a decorative rug. Bright natural light enhances the inviting ambiance.

Condo in Duluth

4.8 out of 5 average rating, 97 reviews

Clock Suite Downtown with Amazing Views

An open living area is highlighted by exposed brick walls and high ceilings, featuring a modern kitchen island and stainless-steel appliances. A spiral staircase leads to an upper level. Natural light floods the space through large windows, showcasing a cozy seating area by a contemporary fireplace.

Condo in Duluth

4.96 out of 5 average rating, 363 reviews

Condo steps away from Lake Superior/Canal Park

Family-friendly house rentals

A secluded cabin is nestled among snow-covered trees under a starry night sky. Warm light spills from large windows, highlighting the wooden exterior and inviting entrance pathway. The tranquil scene is enhanced by a blanket of soft snow framing the cabin.

Home in Finland

4.88 out of 5 average rating, 652 reviews

Gorgeous North Shore river cabin

The exterior of the house features a welcoming entryway with a wooden deck surrounded by greenery. A pathway of concrete leads up to the entrance, flanked by landscaped stones and plants, enhancing the home’s inviting presence.

4.95 out of 5 average rating, 737 reviews

Relax like a local in the heart of Duluth

A cozy fire pit surrounded by a circle of stones is positioned on a gravel patio. Two white Adirondack chairs provide seating, while lush greenery and a distant view of the landscape are visible in the background under a partly cloudy sky.

4.92 out of 5 average rating, 419 reviews

Becks Bungalow

Top guest favorite

The farmhouse, built with traditional wooden logs, is surrounded by lush greenery. A peaceful pond with tall grasses reflects the beauty of the landscape. Outdoor seating is arranged on a deck, offering a welcoming space to enjoy the natural surroundings.

4.97 out of 5 average rating, 215 reviews

The Farmhouse No cleaning fees! Access to Trails!

A cozy living area features a large stone fireplace set within a wooden wall. Natural light floods the space through oversized windows, showcasing greenery outside. A rustic wooden coffee table is centered on a patterned rug, with a combination of comfortable seating options arranged around it.

Home in Beaver Bay

4.9 out of 5 average rating, 112 reviews

Northwoods Luxury on Private Black Sand Beach

Top guest favorite

The cabin is nestled on a wooded point, surrounded by lush greenery and rocky shoreline. The clear waters of Lake Superior gently lap against the bedrock, creating a serene and tranquil setting. Outdoor seating areas and a picnic table are visible on the grassy area.

Home in Two Harbors

4.97 out of 5 average rating, 345 reviews

Classic Vintage Log Cabin on Lake Superior

Top guest favorite

The inviting living room features warm wooden paneling and a gas fireplace centered on a stone facade. Comfortable seating includes a gray sofa and blue chairs, complemented by decorative pillows. Natural light filters through the windows, enhancing the cozy ambiance of the space.

4.96 out of 5 average rating, 196 reviews

Entire home sleeps 7, convenient location

A two-story building is presented, featuring a combination of dark green roofing and beige siding. Windows are positioned on each level, offering natural light. The front entry doors are framed by minimal landscaping, with an expanse of green grass and a gravel pathway leading to the building.

4.92 out of 5 average rating, 196 reviews

Beautiful home or 2 apartments Duluth/Spirit Mtn

Apartment rentals with air conditioning

A comfortable living area features a gray sofa with decorative pillows facing a wall-mounted television. A wooden coffee table sits in front, while a dining area with a round table and four chairs is visible in the background. Neutral-colored walls complement the modern decor.

Apartment in Duluth

4.81 out of 5 average rating, 372 reviews

Grand Getaways Apt. #1

A spacious living room features a large sectional sofa arranged around a low coffee table, offering a comfortable seating area. Natural light filters through the dark blinds on the windows. The rich wood floors enhance the warm ambiance, leading towards a hallway.

Apartment in Superior

4.93 out of 5 average rating, 401 reviews

Historic + Modern lll across bridge from Duluth

A bedroom features a black metal bed frame with a plush, patterned bedspread and layered pillows. The decorative fireplace is highlighted by soft candlelight, and art pieces add a touch of elegance to the walls. Natural light is softly diffused through nearby fixtures.

Apartment in Superior

4.91 out of 5 average rating, 158 reviews

Executive Apt. 1BR 1BA, w/Q Bed

A light-filled living area features modern furniture, including two gray chairs and a plush sofa. A circular coffee table sits in the center, adorned with magazines. Neutral-toned walls are complemented by artistic wall decor. A ceiling fan with lights adds functional elegance.

Apartment in Superior

4.88 out of 5 average rating, 183 reviews

Lovely 2 Bedroom Duplex

A spacious living area is furnished with a gray sectional sofa, accented by throw pillows. A wooden coffee table sits in front, while natural light floods through multiple windows. An open transition leads to the dining area, which features a wooden table and chairs.

Apartment in Superior

4.82 out of 5 average rating, 350 reviews

Stay and Slay in Superior

A modern living space is presented, featuring an inviting round dining table set with dishes and a floral centerpiece. A light-colored sofa is positioned nearby, accompanied by a black coffee table. Art pieces adorn the walls, while natural light brightens the room.

Apartment in Superior

4.88 out of 5 average rating, 270 reviews

Superior Bay Boutique Motel Suite #11

The inviting living area showcases a soft blue sofa paired with a glass coffee table adorned with a decorative vase. A dining area with a light wood table sits next to an open kitchen, featuring stainless steel appliances and warm cabinetry, illuminated by natural light.

Apartment in Superior

4.9 out of 5 average rating, 336 reviews

Terry Flats #4

A metal fire pit is shown with flames rising from a stack of logs. The fire pit features decorative cutouts and sits on a grassy area, surrounded by a white privacy fence.

Apartment in Two Harbors

4.9 out of 5 average rating, 434 reviews

Arcade games & Foosball -Trailer parking #1406

Other great vacation rentals near Chester Bowl Ski Resort

Top guest favorite

A cozy living room features a classic leather sofa and a large area rug. A fireplace is centered beneath a mirror, while natural light enters through multiple windows. A framed art piece of a deer adorns the wall, contributing to the room's eclectic aesthetic.

4.98 out of 5 average rating, 90 reviews

Matilda

The exterior of a mid-century modern home is displayed, showcasing a sloped roof and a combination of brown wooden siding. Lush green grass surrounds the house, while trees provide natural shade. A view of Lake Superior and the sky can be seen in the background.

4.98 out of 5 average rating, 41 reviews

The Denney Hus - Where Olympic Dreams take Flight

Top guest favorite

A child is seen standing on a slight incline surrounded by greenery. The home's modern exterior features large windows reflecting warm light from within, framed by trees and soft outdoor lighting. The area is lush with foliage, offering a serene outdoor setting.

Cabin in Duluth

4.98 out of 5 average rating, 46 reviews

MCM Urban Cabin w/ Finnish Sauna

A yellow cottage with a welcoming porch is shown, featuring two sets of steps leading to the entrance. The porch is adorned with a small seating area. Surrounding greenery and seasonal foliage enhance the rustic charm of the exterior.

Cottage in Duluth

4.89 out of 5 average rating, 135 reviews

Cozy Cottages with a Superior View Cottage #6

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. The space includes a full-size refrigerator, oven, and dishwasher, complemented by ample counter space. Essential kitchen items such as cookware and utensils are thoughtfully arranged for convenience.

Apartment in Duluth

5 out of 5 average rating, 3 reviews

The Perch on London

The living room showcases a gas fireplace and comfortable seating, complemented by large windows that offer views of the surroundings. The bathroom features a soaking tub and modern tile accents. A steam shower is highlighted in the second bathroom, while the bedroom is equipped with a spacious bed and calming decor.

5 out of 5 average rating, 42 reviews

Large Lux Condo | Canal Park | Lakeview | Sleeps 8

Top guest favorite

The bedroom features a wooden bed frame with crisp white bedding and two accent pillows. Flanking the bed are stylish wall sconces, providing gentle lighting. The wall behind the bed showcases intricate patterned wallpaper, adding texture and color to the serene space.

Apartment in Duluth

4.99 out of 5 average rating, 85 reviews

NO cleaning fee- Boutique Guest Suite in Duluth

The tiny house sits elevated among evergreen trees, featuring a wooden deck that extends outward. Large windows allow natural light to flood the interior, while a red front door adds a vibrant focal point to the contemporary exterior.

Farm stay in Wrenshall

4.97 out of 5 average rating, 112 reviews

AirB-n-BAWK! The PERCH @ Locally Laid Egg Company

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