Guesthouse vacation rentals in The Great Lakes

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Top-rated guesthouse rentals in The Great Lakes

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Top guest favorite
A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.
Guesthouse in Chicago
4.99 out of 5 average rating, 903 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Top guest favorite
A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.
Guesthouse in Valparaiso
4.98 out of 5 average rating, 120 reviews

Unique Dome Retreat by Indiana Dunes w/ Lake View

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Top guest favorite
A charming dock is seen illuminated at night with string lights and Canadian flags. The surrounding snow-covered landscape is contrasted by the dark sky. Reflections of the lights are visible on the ice, creating a serene winter scene.
Guesthouse in Shuniah
4.99 out of 5 average rating, 118 reviews

Cozy Winter Cottage on Lake Superior

Escape to the quiet beauty of Lake Superior with this charming winter cottage, just 15 minutes from Sleeping Giant Provincial Park and 45 minutes from Thunder Bay. Nestled right on the shoreline, the cottage offers breathtaking views of the frozen lake and the rugged wilderness beyond. Enjoy cozy evenings by the fire, snowshoeing, ice skating, and add on an ice fishing shack rental for an authentic northern experience. The perfect spot for couples, and adventurers seeking a true winter retreat.

Top guest favorite
A lake house is situated on the shoreline of Lake Erie, featuring a sloped path with steps leading down to it. Soft lights illuminate the exterior during twilight, creating a warm ambiance. The tranquil water extends to the horizon, inviting a peaceful retreat.
Guesthouse in Kingsville
4.98 out of 5 average rating, 727 reviews

Small lake house on Lake Erie shore

Private Bachelor apartment sized house directly on Lake Erie. ULTRA FAST WI-FI, Private deck, Kayaks. The Cottage is always toasty warm all winter long. Queen bed, bathroom with shower, kitchenette. Great swimming in shallow, sandy waters. Cottage is only a few minutes from many area wineries, breweries, distilleries and fantastic restaurants serving local food. Walking distance to Pelee Island ferry. Want something completely different? This is the place. It's almost like staying on a boat.

Top guest favorite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie
5 out of 5 average rating, 228 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Top guest favorite
A cozy living space features a comfortable dark blue sofa complemented by a small wooden table. Two large windows allow natural light to illuminate the area, revealing views of the surrounding trees. A pendant light hangs from a wood-paneled ceiling above.
Guesthouse in Huntsville
4.99 out of 5 average rating, 170 reviews

Muskoka Retreat with Arrowhead/Algonquin Park Pass

Welcome to our beautiful Muskoka Retreat, just 20 mins from the town of Huntsville. There is a complimentary Provincial Park Pass provided, between check in and check out times. The decor is fresh and intimate, with warm wood accents. Our property is surrounded by trees, on 10 acres of forested land, where you can enjoy the company of many species of birds and wildlife. The guest house is completely separate and private, from our home, which is 50 feet away, and it was newly built in 2022.

Top guest favorite
A serene sleeping area features a queen bed with a green quilt and decorative pillows. Flanking lamps provide soft lighting next to the bed. A forest-themed wall mural enhances the calming atmosphere, while a window offers a glimpse of the outdoors.
Guesthouse in Sayner
4.97 out of 5 average rating, 220 reviews

Sauna&Silent Starry Eves at Lands End at Edge Loft

Cozy zenny retreat in Wisconsin's Northwoods. Deck overlooks NHAL wilderness. AS OF 12/10 15" SNOW! Rustic SAUNA steps away.Winman ski, snowshoe & fat tire bike trls open. Hide away at the Loft: birdwatch, listen to howling wolves, watch snow fall via floodlight. Gas grill, firetable.WIFI, elect FP, kitch, full fridge. Escanaba/Lumberjack St Trls in 5min. Glide ice skate ribbon: 10. Winman Trls groomed Xcountry skiing: 30. Snowshoe trl out your door! Semi-seclud yet 8mi to BJ restaurants!!

Top guest favorite
The modern carriage house is illuminated by exterior lighting, showcasing its sleek design. A motorcycle is parked on the gravel drive beside the building. The structure is set against a backdrop of the city skyline, with large windows providing glimpses of the interior.
Guesthouse in Detroit
4.96 out of 5 average rating, 537 reviews

Sky Carriage House: Light, Bright, Corktown Escape

You'll be staying in our newly constructed carriage house at the back of our property in the heart of Corktown - Detroit's oldest historic neighborhood. This private dwelling is accessed from the back alley entrance and offers high ceilings and a panoramic view of downtown and the surrounding neighborhood. The unit features 1 bedroom/1 bath, living, dining, laundry and a full kitchen. In warmer months a small cafe seating area is situated on the spanish rock drive along the green alley.

Top guest favorite
A quaint cottage stands surrounded by snow-covered trees, with a light grey door and window accents visible. The structure features a simple white exterior, complemented by a winter landscape of freshly fallen snow, creating a serene and peaceful atmosphere.
Guesthouse in Fish Creek
4.97 out of 5 average rating, 265 reviews

Vintage Mod Cottage with fireplace & soaking tub!

Grandview Farm Cottage is a circa 1920s newly renovated, 420 sq. ft. private guesthouse on the grounds of a 2.5 acre Door County property built in the late 1800s. Modern, industrial and repurposed style meets vintage farmhouse charm. Central location allows for quick drive or even a bike ride to either coast of the peninsula. Enjoy nature, wildlife, your own organically grown gardens, and dark starry night skies, while being only 3 miles to nightlife and shopping and beaches and parks.

Superhost
A loft area features a spacious bed adorned with decorative pillows and a soft throw. Large windows frame a scenic view of Lake Huron, allowing natural light to fill the wooden interior, highlighting the warm tones of the walls and floor.
Guesthouse in Lambton Shores
4.85 out of 5 average rating, 177 reviews

Bluecoast Bunkie on stunning Lake Huron.

Find Bluecoast Bunkie nestled in the trees on a cliff overlooking Lake Huron. Fall asleep to the sound of the waves lapping on the shores and wake up to the choir of birds singing while enjoying a cup of artisan coffee or tea on your private deck. Take a stroll down long stretches of shoreline, seldom visited by others. Lounge on the private beach or beside the indoor salt water pool. Finish the day on the lookout while witnessing the most spectacular sunsets this world has to offer.

Top guest favorite
A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.
Guesthouse in New Buffalo
4.97 out of 5 average rating, 644 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Top guest favorite
A newly renovated guesthouse is showcased, featuring a wooden exterior and a spacious deck. Comfortable patio furniture, including a red chair and two black chairs, adorn the deck. Stone pathways lead to the entrance, surrounded by well-maintained greenery and trees.
Guesthouse in Niagara Falls
5 out of 5 average rating, 231 reviews

Hilltop Hideaway

A unique, newly renovated guesthouse nestled on 5 acres ,surrounded by trees with a private walking trail. Just 10 minutes from Niagara Falls and Niagara on the Lake!! 2 minutes to the Niagara Wine Route and many restaurants, wineries, and shopping. Modern farmhouse charm and decor throughout this open concept one bedroom guesthouse. A perfect retreat to relax, restore and explore Niagara.

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