
Places to stay near Chester Bowl Ski Resort
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Top-rated holiday rentals near Chester Bowl Ski Resort
Guests agree: these stays are highly rated for location, cleanliness and more.

NO cleaning fee- Boutique Guest Suite in Duluth
Welcome to your sweet escape at Allendale Orchard in Duluth! A perfect oasis for a couple or solo traveler. Relax on your private deck or in the soaking tub after a day of exploring all that Duluth and the North Shore has to offer. You’ll be close to an abundance of hiking and biking trails, minutes away from quaint coffee shops and award winning restaurants, and can pick your own seasonal fruit right on the property. We’re here to offer all of our guests a personalized and inviting experience!

Entire home sleeps 7, convenient location
Just 10 minutes (or less) away from so many wonderful things Duluth has to offer. Walking distance to restaurants and frozen yogurt bar! Living room features a gas fireplace. Dining room table great for games and dining! You will find charm in every corner of this 1938 home. Located in a quaint neighborhood with easy access to main roads. It is a great launching point for all your sightseeing activities, or to just kick back and relax. It's your vacation, we hope you enjoy it! Duluth PL 23-001

Matilda
Escape life, for a moment, to this enchanting vintage home with eclectic vibes. The spacious home has one king room, one queen room, and one full room, all curated in the coziest north woods elegance . Let the wind from lake superior slap you in the face as you sit on the back deck. The home is in a commercial part of town with a two minute walk to lake walk. If you take a right and you are a 10 min bike ride from Canal park . If you take a left your a 10 minute bike ride from Glensheen.

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.

Bentleyville 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!

Private Lake View Hike/Bike Trail Access King Bed
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 King 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

Executive Apt. 1BR 1BA, w/Q Bed
A charming, historical accommodation has prepared a place for you. This special place is close to everything, making it easy to plan your visit. One bedroom and one bath with immaculate, delightful decor. This home away from home is only blocks away from downtown Superior restaurants, vibrant nightlife, quaint coffee shops, and sweet, unique boutiques. Either that, or you might want to order in, put your feet up, relax, and watch a film. We look forward to your visit!

Entertainment & Outdoor Activities - Hub
Stay in the heart of Duluth—your ideal base for both vacations and business trips. Just minutes from Lincoln Park’s Craft District, Downtown, and Canal Parks local breweries, cider houses. Adventure awaits with quick access to Spirit Mountain, the Munger State Trail, hiking, mountain biking, paddling, boating, fishing, birdwatching, and more. Experience the perfect blend of comfort, convenience, and outdoor fun in one of Duluth’s most exciting neighborhoods.

The 5 West Bungalow
Relax and kick back in this 2 bed/1 bath, pet friendly home Conveniently centered amongst everything Duluth has to offer! Jake and I are fully committed to providing you the Home away from Home. No management company here, NO CLEANING FEES, we do it all by ourselves. Communication, laundry, cleaning and maintenance - our reviews show we take pride in the place. Now if we could only figure out how to provide the perfect weather!!!

Stay and Slay in Superior
This cute updated 2 bedroom apartment has everything you need! Whether your'e on a short business trip or taking a lengthy vacation to enjoy the beautiful Twin Ports, my apartment provides the perfect location. Only blocks away from restaurants and bars on the famous Tower Avenue and less than 10 minutes from Canal Park in Duluth. Pattison Park and Amnicon Falls are also only a short drive away!

Cottage with Lake Superior & North Shore views
Tucked away on 1.5 acres in the middle of Duluth, this one-bedroom cottage has breath-taking panoramic views of Lake Superior, the Aerial Lift bridge and the St. Louis River. With the large property and surrounding trees, the home feels secluded but has wonderful access to hiking and biking trails, parks, beaches and all that downtown Duluth and Canal Park have to offer. License PL23-023

Grand Getaways Apt. #1
Welcome to your secure and cozy haven! Our Airbnb boasts cleanliness, a super comfy bed, and is conveniently located just a mile from Spirit Mountain ski resort, hiking trails, and the zoo. Fuel up for your adventures at our family-owned restaurant downstairs, offering healthy breakfast or lunch options. Your comfort and safety are our priorities – your perfect getaway starts here!
Popular amenities for holiday rentals near Chester Bowl Ski Resort
Apartment rentals with wifi

Main Street apt 2 blocks from Lake Superior!

Stay Lincoln Park 2 | Craft District Condo

One Minute Walk to Lake Superior. Brookside #11

Bluewater: Breathtaking Lake Superior Views

The Fireside at Silver Creek B&B w/ SAUNA

One Bedroom Condo on Lake Superior

Aurora Black | The Brix | Pool in Canal Park!

Stoney Brook Nook on the shore of Lake Superior
Family-friendly house rentals

Cozy 2 bedroom, 8 twin beds, 1 bath, full kitchen

Original Hillside Home

Buffalo Bliss-Near Universities-Large Deck/Yard

Two Harbors Area Wild Grape Cottage

Historic Tudor Cottage | Cute 3 Bedroom Home

Luxurious house for nature-lovers by Hartley Park

Nice 3 bedroom house with a view

House on the Hill Duluth-Epic Lake Superior Views
Apartment rentals with air conditioning

Large 2 Bedroom near Lake Superior

Clean, mid-century/modern apt.

Burlington View Stays License#1472

Superior Bay Boutique Motel Suite #11

3rd Avenue comfortable apartment In Two Harbors

Studio Apartment at Lake Superior Brewing Brewtel

Historic Modern 10 min across bridge to Duluth

Beautiful, private vacation space
Other great holiday rentals near Chester Bowl Ski Resort

MCM Urban Cabin w/ Finnish Sauna

The Perch on London

Bayfield Rustic Yurt 2 (Terra Cotta)

Superior View

The Itty-Bitty Inn

Haines Haven
Experience Duluth Arts in the BB Makers Loft

Sölveig Stay: Shipping Container with Nordic SAUNA




