Guesthouse holiday rentals in The Great Lakes

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

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.

Unique Guesthouse on Lake Huron - Great Sunsets!

Private, self-contained, fully furnished, 2 bedroom guest house, overlooking Lake Huron, with access to a quiet, Community private sand beach, unbelievable sunsets, rated in the top 10 worldwide, by National Geographic. Ideal spot for quiet vacations or a romantic get-a-ways. Best suited for couples, small families, or someone looking to just “get away from it all"– a true hidden gem located in southwest Ontario. Beautiful gardens, winery's, golf courses close by - What are you waiting for?

Riverside Retreat—Kayaks included!

Lovely peaceful retreat on Intermediate River. Steps to downtown Bellaire: Short’s beer, unique stores, restaurants and movie theatre. This tranquil space is the perfect romantic getaway for 2 In the heart of Michigan’s prime recreation area, minutes away from championship golf courses, ski runs, hiking, biking trails and beautiful Torch Lake. Enjoy wine tasting, craft beer, Mammoth Craft Distillery and Bee Well Cider and Meadery, or just select a book from our library and relax on the dock!

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 21-26 (5 nights/6 days) JUNE 27-JULY 6 JULY 8-18 JULY 26-31 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake

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.

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.

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

The Carriage House in the heart of Wine Country

Welcome to your relaxing escape on our organic flower and herb farm, nestled on the scenic Beamsville Bench. Unwind with a glass of local wine on your private deck, stroll through fragrant gardens, or explore the nearby Bruce Trail. Just minutes from 40+ wineries and top dining spots. Only 30 minutes to Niagara Falls and 45 to Niagara-on-the-Lake. A peaceful retreat perfect for nature lovers, wine enthusiasts, and romantic getaways.

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

The Cedar Rose

Built in 2018, our off-grid cedar cabin is tucked away in a mixed woodland on beautiful Manitoulin Island. It is uniquely decorated with antiques, thrift store finds and handicrafts collected from our travels around the world as far as Africa, Japan, Costa Rica and Canada’s Arctic. Our space is an inviting space to unwind, unplug and wake up to the sounds of the birds after enjoying the stars on a clear night.

Cozy Cottage in Kawartha Lakes

This cozy cottage will have you enjoying a tranquil experience with plenty of gorgeous views. Sitting on the edge of Lake Scugog. A plethora of opportunities await the adventurous, with trails minutes away. Historical Port Perry and Lindsay for all your dining and shopping experiences. Additionally, there is an amazing casino and an 18 hole golf course conveniently located.