Holiday houses in Madison

4.99 out of 5 average rating, 231 reviews

A winterized hot tub is surrounded by lush greenery, with soft blue lighting illuminating the water. A gravel fire pit area nearby features log seating, and warm string lights are draped on an adjacent tree, creating a serene outdoor atmosphere for relaxation.

Cottage in Madison

Vineyard View | Walk to Wineries & River| Hot Tub

The Vineyard View, a unique gem in the heart of wine country! Immerse yourself in the beauty of this charming home nestled on the Grand River cliffs with stunning Metro Park scenery as your backdrop. • Short stroll to local wineries or drive just minutes to visit many others! • Relax on the patio • Soak in the 6 person winterized hot tub with massaging jets • Sip coffee while admiring the vineyards • Explore the river via the Metro Park trails in the backyard with your fishing pole in hand.

4.96 out of 5 average rating, 236 reviews

A charming cottage features bright yellow exterior walls with aqua accents. A welcoming front door is framed by a small window. Lush green landscaping surrounds the entrance, which is paved with brick, leading to the inviting front porch.

Guesthouse in Madison

LemonDrop Lake-Front Cottage

Fully remodeled in 2023 LemonDrop Cottage is a Lake-Front property, with direct access to Lake Erie. Lake viewable from Kitchen or Bedroom windows. Mar-2023 all New Windows, Bathroom doubled (2x) in size, new 12K AC. 2021-Hickory hardwood floors,, shower, hot water heater, oven, kitchen table/chairs, king size mattress, sofa-bed, BBQ grill (propane provided), and fire pit with wood provided. Built in 1949 as a fishing cottage, adorable Lake-Front Cabin with private stairwell down to the water.

A cozy living room is framed by large windows that allow natural light to fill the space. A sectional couch is adorned with various patterned pillows, while a wooden coffee table holds decorative items. A plush area rug adds warmth to the hardwood floor.

4.99 out of 5 average rating, 132 reviews

White Sands Lake House

Welcome to a timeless retreat by the water - a century-old home that marries modern comfort with historic allure. The house boasts an abundance of original charm, featuring wood paneling, beams adorning the ceiling, and the original hardwood floor. The light and airy kitchen include quartz countertops, new cabinets, appliances, and luxury vinyl plank flooring. The spacious bedrooms, living area, and dining room are caressed by daylight, creating an ambiance that is both uplifting and soothing.

4.95 out of 5 average rating, 275 reviews

Guesthouse in Chardon

Chardon Loft

Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

4.96 out of 5 average rating, 233 reviews

A cozy living space features rustic wood paneling and two comfortable wooden rockers positioned beside a small table. A sectional sofa provides ample seating, while a soft rug lies on the polished hardwood floor. Natural light filters through the window adorned with blinds.

Apartment in Madison

Cozy winery getaway with hot tub!

Relax in this cozy country garage apt. in Grand River Valley. The first stop on your winery tour is just 4 minutes away with over 30 more to explore. Visit nearby Lake Erie, Thompson Ledges, Geauga Park District Observatory, or a covered bridge. Kitchenette w/ mini fridge, microwave, Keurig & sink. Quaint bath w/ stand up shower Private keycode entry Electric fireplace King size bed Rustic wood rockers & table Pet friendly Shared access to hot tub, back yard fire pit & patio

4.98 out of 5 average rating, 120 reviews

A spacious deck furniture arrangement is seen overlooking Lake Erie, with a glass-top table and cushioned seating. The serene water reflects the warm hues of the sunset, while lush greenery frames the view, providing a sense of tranquility and connection with nature.

Cottage in Madison

Lakeview Cottage | Stunning Sunsets & Lake Views!

Enjoy a spacious, 3-bedroom cottage in a quiet, scenic neighborhood along the shores of Lake Erie. Take in stunning views with friends and family at this hidden gem, featuring a patio heater (fall/spring) to stay cozy on chilly nights. Minutes from Madison and Geneva wineries, and about 20 minutes to Mentor Headlands Beach and Geneva-on-the-Lake. Walk to a scenic park with a playground, picnic area, and beautiful lake views. Visit a public golf course just down the road.

The exterior of a ranch-style home features a vintage sandstone façade complemented by a modern grey roof. Surrounded by greenery, the yard includes patches of grass and shrubs, with remnants of snow remaining, presenting a serene atmosphere at dusk.

4.99 out of 5 average rating, 185 reviews

Sandstone Ranch

Welcome to Sandstone Ranch! This peaceful, charming 3 BR, 1.5 Bath ranch style home in the heart of the Grand River Valley is completely remodeled, combining a clean, timeless interior design with modern amenities and vintage charm. This is the BEST location in Lake County, minutes away from ALL the wineries, distilleries, restaurants, Historic Madison village, Geneva-on-the-Lake, Spire institute, I-90, Powderhorn golf course, and Steelhead fishing at the Metroparks!

4.98 out of 5 average rating, 360 reviews

A spacious bedroom features a wooden ceiling and large windows allowing natural light to filter in. A full-size bed is dressed with a patterned coverlet, complemented by a seating area consisting of a chair and a small table. Decorative elements include artwork and a patterned rug.

Guest suite in Perry

THE KELBY: Private Spacious Suite Near Grand River

Artfully decorated and resort-like, The Kelby ABNB is an absolute gem! It is a 1000 sqft loft on 3 acre wooded ravine: scenic vista with many windows. Half mile from outdoor YMCA trails. Owner provides list of favorite local haunts. Exceptionally clean&fresh.Visit wineries, hike, kayaking, antique stores. Kitchenette/breakfast area with amenities: juice, cereal, breakfast foods. Bedding, towels, and toiletries provided. Private. Quiet. Comfortable.

A bright, open-concept living space is featured, showcasing modern kitchen appliances and a large island with bar seating. A dining area with a dark wooden table and decorative bowl is visible, along with comfortable seating in the living area. Large windows allow natural light to fill the room.

4.93 out of 5 average rating, 199 reviews

Vincent William Wine: Lakefront winery guest house

This beautiful guest house is located on the property of Vincent William Wine Restaurant, Inn, and Wine Bar in Grand River Valley Wine Region. With a beach, close proximity to many area Wineries, Geneva on the lake, and other tourist attractions, the Guest House is the most ideal place for all your getaway fun. kayaks are also available upon request. Take a 5 min walk and enjoy an ice cream shop, or the several restaurants and bars.

4.96 out of 5 average rating, 225 reviews

A historic two-story house features a covered front porch with white railings, adorned with seasonal decorations. Two blooming trees add color to the front yard, while manicured grass and a paved pathway lead to the entrance. The exterior showcases classic architectural elements.

Guest suite in Geneva

Lorentus' Century Home

Enjoy the charm of our century home built in 1884. Close to antique shops and downtown Geneva and ten minutes to Geneva-on-the-Lake and many local wineries. Enjoy your morning coffee on the front deck. The space offers a stocked kitchenette for light meals, full bathroom with a shower and a large bedroom/living area with an adjustable queen sized bed, internet, smart TV with HDMI cable. (No cable television).

4.91 out of 5 average rating, 116 reviews

A charming exterior view of the cottage presents a coral front door adorned with a greenery wreath. The light siding is complemented by a small, accessible staircase leading to the entrance, while a wooden privacy fence and lush trees provide a natural backdrop.

Cottage in Madison

Cottage w/fenced yard by beach, wineries, & Spire

Enjoy this beautiful cottage near everything that matters! Walk to a Lake Erie beach, lakefront park, winery or several restaurants and bars. Better yet, travel just minutes east or south to WINE COUNTRY! Situated on a spacious lot on a quiet street, the cottage is pet friendly with a fenced in back yard. It also features a fire pit and outdoor seating area.

4.95 out of 5 average rating, 361 reviews

A rustic wooden cabin is nestled among trees, featuring a covered porch with a table and chairs. The front door is white, and a decorative window adds charm. Surrounding foliage suggests a serene, natural setting, conducive to relaxation.

Cabin in Geneva

Hemlock Hideaway-Rustic Cabin on the Grand River

This primitive cabin nestled in the woods overlooking the Grand River is a nature-lover's paradise! Come canoe, fish, experience wine country, or unplug and just get away from it all. Please note: There is no running water or electricity at the site, but the cabin is generator-ready and there is an outhouse. See below for more details.

Popular amenities for Madison holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Madison

4.92 out of 5 average rating, 52 reviews

A dedicated coffee station is displayed, featuring a coffee maker, sugar, and coffee canisters. A small plant adds a touch of greenery. Four coffee mugs hang from a rack above a clean, white shelf, complemented by a rustic sign that reads 'coffee bar'.

Home in Geneva

Thomas Getaway

A deck with red wooden planks features a small outdoor table and chairs. A white door leads to the adjacent building, with a light-colored facade. Lush green shrubbery and grasses border the area, providing a natural touch to the outdoor space.

4.92 out of 5 average rating, 48 reviews

Near Lake Erie, SPIRE, Vincent William Wine, GOTL

4.95 out of 5 average rating, 37 reviews

A vibrant mural decorates the exterior wall, featuring an array of colorful flowers such as sunflowers, butterflies, and a variety of blossoms. Above the artwork, the words 'GENEVA OH' are boldly displayed, while solar panels are installed on the roof.

Tiny home in Geneva

Cozy Shed-Teau in Geneva

4.86 out of 5 average rating, 51 reviews

The cabin's exterior showcases wooden log construction, with a front porch featuring sturdy railings and steps leading to the entrance. A small storage shed is positioned nearby, surrounded by gravel. The setting is framed by bare trees, indicative of the season.

Cabin in Ashtabula

The Getaway

5 out of 5 average rating, 66 reviews

A loft bedroom is displayed featuring a double bed dressed in a neutral quilt and decorative pillows. Two bedside lamps flank the bed, and framed artwork adorns the walls. Natural light enters through a small window, and wooden flooring adds warmth to the space.

Cabin in Madison

Wine Country Woodland Retreat

5 out of 5 average rating, 26 reviews

A charming cottage nestled among tall trees is viewed from a path illuminated by garden lights. A wooden bridge connects the path to the cottage's expansive porch, which is framed by large windows, allowing for an inviting glow in the evening light.

Cabin in Geneva

The Bent Tree Cottage at Vineyard Woods

Superhost

A spacious living room features two comfortable sofas facing a coffee table. Natural light enters through a nearby window, illuminating the laminate flooring. In the background, a dining area with a wooden table and chairs is visible, leading to a well-equipped kitchen.

Home in Geneva

4.7 out of 5 average rating, 66 reviews

Cozy | SPIRE | Winery Tours | GOTL | Beach