Holiday rentals with outdoor seating in Bayfield

A bright living room is characterized by light wooden flooring and natural light. Two white sofas are positioned around a wooden coffee table, with a decorative lamp on one end. A large television is placed in front of a wooden cabinet, and a doorway leads to the rest of the condo.

4.98 out of 5 average rating, 159 reviews

Captain's Cabin

Centrally located in the heart of downtown Bayfield--this charming, ground-level condo is just steps away from restaurants, coffee shops, and a block from City Dock and the Lake. The 830 sq.ft condo sleeps 4. A spacious bedroom holds a king bed while the living room has queen sleeper sofa. Located in the historic George Crawford House on one of Bayfield's classic brick lined streets, private parking is provided at the rear of the building with a short walk to the best of everything in Bayfield.

4.97 out of 5 average rating, 148 reviews

The modern cabin features a unique timber frame design and large glass windows, offering expansive views of the surrounding landscape. The exterior is complemented by natural stone and landscaped areas with vibrant fall colors, adding to the serene environment.

Cabin in Two Harbors

Architect-designed, net zero home w/ stunning view

Great for a couple's getaway or family excursion, perfectly located on the North Shore with a spectacular view of Lake Superior. Features stunning timber frame modern design, luxurious master bed and bath, spacious deck, and porch with fireplace. There's nothing else like it on the North Shore. It is perfectly located 20 minutes from Duluth and 5 minutes from Two Harbors, 5 from a boat launch. Our cabin is certified as Net Zero Ready through the DOE and was designed and built by Timberlyne.

4.98 out of 5 average rating, 346 reviews

The cabin exterior features logs and a screened porch, offering shaded seating. A wooden deck wraps around, and steps lead up to the entrance. A propane grill is visible, and greenery surrounds the space, providing a secluded atmosphere.

Cabin in Bayfield

The Copper Squirrel of Little Sand Bay DogsWelcome

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

4.97 out of 5 average rating, 199 reviews

A private deck features a glass table surrounded by two chairs with cushions, complemented by vibrant planters. In the background, a lush garden blooms with various flowers and greenery, creating an inviting outdoor retreat.

Guest suite in Brule

The Bee's Balm

You'll find us tucked in the quiet woods of northern WI near the Brule River. We're remote enough to experience star-filled skies & fireflies, but not far from many premier attractions. Your space is a self-contained apartment on the lower level of our 2.5 story home. It features a private entry, queen-sized bed, kitchenette, lower level private deck, access our beautiful grounds & more! We're a family of artists who love to travel & to introduce others to our beautiful part of the world.

4.81 out of 5 average rating, 115 reviews

A rustic cottage is surrounded by colorful autumn foliage, showcasing its wooden exterior and A-framed roof. A large porch with steps provides entry, and a pathway leads through the grassy yard, where scattered leaves complement the natural setting.

Cabin in Port Wing

Cozy South Shore cottage near Lake Superior

Enjoy the splendor of Lake Superior at our cozy, rustic cottage near Port Wing, WI. Situated halfway between Duluth/Superior and Bayfield, it's the perfect location to visit all your favorite South Shore locations. There's no need to choose between privacy & the difficulties of accessing remote properties. Our cottage is located within 68 acres of private, wooded wilderness. Yet since we're next to the Wisconsin Lake Superior Scenic Byway (Hwy 13), it's easy to get wherever you want to go!

4.88 out of 5 average rating, 172 reviews

The modern cabin is nestled among tall trees, featuring a large screened porch that is partially framed by natural surroundings. Soft light filters through the foliage, creating a serene atmosphere. Lounge chairs are positioned near the porch, enhancing the inviting outdoor space.

Cottage in Bayfield

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts. Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen • Boat Slip Rental Available

A studio space features a spacious bed and a queen sofa sleeper, accented by neutral-colored walls. Natural light enters through a nearby window, illuminating the cozy sitting area with its black couch. A small dining table and kitchenette are seen in the background.

4.8 out of 5 average rating, 380 reviews

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

4.99 out of 5 average rating, 395 reviews

A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.

Guesthouse in Ashland

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

4.99 out of 5 average rating, 150 reviews

The cottage exterior features a wooden entrance with a small deck, surrounded by a snowy landscape. Icicles hang from the eaves, and evergreen trees are visible nearby. Window boxes adorned with greenery add a touch of charm to the entrance.

Cottage in Cornucopia

Borealis Cottage by Siskiwit Bay

Borealis Cottage sits on a 2-acre, private, wooded lot in the sustainably designed Sawgrass Community of Cornucopia. Light-filled cottage with open floor plan includes a sleeping loft, screened porch, gas fireplace, and fully-equipped kitchen. A quick, quiet walk from the cottage takes you to a private wooded path with access to Cornucopia Beach on Siskiwit Bay. Explore the Apostle Islands National Lakeshore--our cottage is located 4 miles from Meyers Beach and 20 miles from Bayfield.

4.94 out of 5 average rating, 232 reviews

A rustic A-frame cabin is nestled among tall evergreen and birch trees, with fresh snow covering the landscape. The entrance features two large windows framed by wood and two doors. A wooden deck extends towards the tranquil woodland, creating an inviting outdoor space.

Cabin in Herbster

South Shore A-Frame: Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern Aframe off Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

4.99 out of 5 average rating, 150 reviews

The modern home is surrounded by lush greenery, with large windows reflecting the evening light. A staircase with railings leads to the entrance, enhancing accessibility. A circular window adds a unique architectural feature, while soft lights illuminate the exterior, creating a serene nighttime ambiance.

Cabin in Herbster

Superior Sunsets @ The West Slope (Steam Shower)

Our 3 bedroom, 2 bath home is located 1 mile out of Cornucopia and 20 miles from Bayfield. Nestled in a lush forest on a sandstone cliff overlooking Lake Superior, this home is a new build featuring a STEAM SHOWER , a fully equipped kitchen and cozy gas fireplace . Deck with grill and stunning sunset views. Large entertainment room w/ 65" Smart T.V. , POOL TABLE & DART BOARD. Outdoor firepit and picnic table. WE PRACTICE ENHANCED SANITIZING MEASURES WITH EVERY TURNOVER.

4.94 out of 5 average rating, 456 reviews

The exterior of a red yurt is surrounded by lush greenery and autumn foliage. A wooden staircase leads up to the entrance, while a chimney indicates a wood stove inside. A cloudy sky is visible above, adding to the serene ambiance of the setting.

Yurt in Bayfield

Twisting Twig Gardens and Orchard Yurt

Our yurt offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

Popular amenities for Bayfield outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 138 reviews

An open-concept living space showcases polished concrete floors and a stylish kitchen area. A curved staircase leads to upper levels, while bar seating with green stools invites gatherings. Large windows allow natural light to spill in, highlighting the exquisite tile work on the backsplash.

Home in Two Harbors

Cabin in Knife River with Sauna and Amazing Views

4.87 out of 5 average rating, 171 reviews

A small wooden dining table is positioned against the wall, accompanied by two white, spindle-back chairs. A light plaid table runner is placed across the table. Natural light filters in through a nearby window, creating a warm and welcoming dining space.

Home in Ashland

Bungalow (House) on Chequamegon Bay.

4.88 out of 5 average rating, 247 reviews

The exterior of the farm-style house is shown, featuring a welcoming porch and multiple windows. A large tree is positioned to the right, contributing to the home's charm. The building's blue siding reflects a serene aesthetic under a partly cloudy sky.

Home in Ashland

Entire- Cozy Chequamegon Home

4.94 out of 5 average rating, 131 reviews

The exterior of the home showcases a wooden façade surrounded by lush greenery and tall trees. A fire pit surrounded by log seating sits in the foreground, offering a relaxing outdoor space. A patio with chairs and an umbrella is visible near the entrance.

Home in La Pointe

Henny Penny-Quiet and Close to Town

4.99 out of 5 average rating, 103 reviews

A modern and cozy living area is presented, featuring a gray sofa, a wooden coffee table, and two accent chairs. A flat-screen television displays a flickering fire, while a set of books and games is arranged on a white shelf beside a staircase with black risers.

Home in Two Harbors

La Casita +sauna North Shore retreat

4.97 out of 5 average rating, 223 reviews

The exterior of the farmhouse is featured, showcasing a traditional log structure surrounded by vibrant flower gardens. A variety of colorful blooms in yellow and pink create a picturesque setting, while a serene pond with rocks adds to the natural beauty of the landscape.

Home in Brule

The Farmhouse Lovely snow! Access to Trails!

4.98 out of 5 average rating, 115 reviews

A spacious kitchen features wooden cabinetry and a large central island with a dark countertop. A stylish clock adorns the wall among neutral-toned tiles. Modern appliances, including an oven and microwave, enhance functionality. Natural light promotes a bright ambiance.

Home in Iron River

Driftwood/Trails End Lodging/Entire Home

4.98 out of 5 average rating, 263 reviews

A fire pit is surrounded by four black wooden chairs featuring patterned cushions. The dark exterior of the two-story house is visible in the background, complemented by a green roof and an expansive wooden deck. Lush trees and grassy areas surround the property.

Home in Brule

The Black Spruce (No Cleaning Fee! Access Trails!)

Apartment rentals with outdoor seating

The open living area features large south-facing windows allowing natural light to fill the space. A comfortable gray sofa and a supportive chair are arranged on a patterned rug. A small table is set up for work or dining, complemented by greenery from nearby plants.

5 out of 5 average rating, 85 reviews

Sunny + Quaint Rental in the Heart of Bayfield

A cozy living area features a comfortable gray sofa and a plush red armchair, accompanied by a wooden coffee table. The room is divided into a sleeping area with a queen-size bed, adorned with light-colored bedding. Soft lighting enhances the welcoming atmosphere.

4.82 out of 5 average rating, 123 reviews

Lake Superior Getaway. Hillside Suites Unit #1.

The ground-level patio features outdoor seating with a table and chairs, set against a backdrop of landscaping that includes ornamental grasses and a rose bush. Two entrances with glass doors provide access to the living spaces above.

4.89 out of 5 average rating, 61 reviews

Easy access ground level condominium

4.98 out of 5 average rating, 269 reviews

The exterior of the house is presented at dusk, highlighted by string lights creating a warm ambiance. A picnic table is positioned on a paved area, accompanied by a grill. Lush greenery surrounds the property, enhancing the tranquil forest setting.

Apartment in Washburn

Palma Lodge

4.81 out of 5 average rating, 323 reviews

A comfortable living area features a black sofa adorned with decorative pillows, positioned against a light-colored wall. Natural light filters through large windows, draped with patterned curtains. A wooden armchair and soft area rug complement the inviting space.

Apartment in Two Harbors

3rd Avenue comfortable apartment In Two Harbors

A view of the serene Lake Superior is framed by large glass doors, leading to a private deck. The seating area features a cozy sofa and a light wood coffee table, complemented by a dining space with wooden chairs. Natural light illuminates the interior.

4.93 out of 5 average rating, 30 reviews

Bayfield Island View "Fedora" on Lake Superior

4.92 out of 5 average rating, 192 reviews

A comfortably arranged living area features a dark sofa with decorative cushions, a small wooden desk with a chair, and a wall-mounted television. The decor includes a stylish area rug, while natural light is provided by a nearby window.

Apartment in Two Harbors

Port 606

4.9 out of 5 average rating, 475 reviews

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

Arcade games & Foosball -Trailer parking #1406

Condo rentals with outdoor seating

4.98 out of 5 average rating, 108 reviews

An outdoor dining area features a black metal table surrounded by six matching chairs. The setting is complemented by a view of the lake, with grassy areas and trees visible in the background. Light filters through the trees, creating a serene atmosphere.

Condo in La Pointe

#1 Lakeside

A wooden dining table with four chairs is positioned in the center, accompanied by a stationary menu holder. A comfortable couch is visible in the background, facing a light-filled sliding door leading to a balcony. Warm lighting from lamps adds a cozy ambiance.

4.82 out of 5 average rating, 87 reviews

Downtown Bayfield 2 BR Condo fireplace sleeps 6

A modern studio condo interior is presented, featuring a spacious bed with a quilted coverlet. A gas fireplace offers warmth, while large windows frame panoramic lake views. A light-toned armchair and decorative shelves enhance the cozy ambiance, with a bright door leading to an outdoor space.

4.91 out of 5 average rating, 133 reviews

Beachfront Condo -Stunning Views & Convenience All

A large set of sliding glass doors provides a view of the marina and water, illuminated by natural light. A red umbrella shades a dining table on the deck, while a comfortable seating area with light-colored furniture is positioned nearby.

4.97 out of 5 average rating, 58 reviews

Bayfield on the Lake - Waterfront Condo Downtown

5 out of 5 average rating, 17 reviews

A spacious living area features a large sectional sofa facing a contemporary TV and a wood stove. Natural light fills the room through expansive windows, offering a view of the lake and surrounding landscape. A fan hangs from the wooden ceiling, adding to the cozy atmosphere.

Condo in Two Harbors

Lake Superior Condo With Waterfront Views + Access

Condo in Two Harbors

New place to stay

Pool & hot tub, condo, views, lakeshore

5 out of 5 average rating, 29 reviews

Condo in Two Harbors

Superior Lakefront 2BR | Pool • Hot Tub • EV

Superhost

Numerous sailboats are captured against a clear blue sky, their masts reaching upward into the sunlight. The bright sun creates a halo effect, illuminating the boats and creating a serene atmosphere in the marina setting.