Vacation rentals in Madison

4.87 out of 5 average rating, 172 reviews

An outdoor deck is presented with a black metal table and four matching chairs. Sunlight casts stripes across the wooden flooring, which is partially covered in snow. A small dog is seen enjoying the space, with a scenic view of trees and hills in the background.

Townhouse in Galena

Galena Territories 3 level Townhome Sleeps nine

Beautiful vacation home in Galena Territories. Located in central resort core, close to all 4 golf courses, owners club, hiking trails and main lodge. Only 15 minutes drive from historic Galena IL. Three level townhome, large screen TV in living room and family room all bedrooms have HDTV. Upper level BR w/en-suite bathroom. Two BR’s are full sized showers/tubs. All linens/toiletries/coffee/condiments provided. Wood burning fireplace with wood provided. Free access to all owners club facilities.

4.85 out of 5 average rating, 133 reviews

A lakeside view of a vacation rental home is visible, situated on a spacious lawn surrounded by trees. A private dock extends into the calm waters of Lake Sinissippi, reflecting the serene landscape and clear sky.

Home in Juneau

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This newly updated home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr.

4.83 out of 5 average rating, 231 reviews

A serene view overlooking Crandalls Bay is captured, featuring a calm body of water surrounded by lush greenery. Several boats are docked along the shore, with a grassy area leading to the water. A tree provides shade in the foreground, adding to the natural setting.

Condo in Wisconsin Dells

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

**INDOOR & OUTDOOR POOL ACCESS | DISCOUNTED ATTRACTION TIX | WATERFRONT** The Riverwalk Retreat is the perfect spot to enjoy your next WI Dells trip with friends or family. This cozy vacation rental is located at the Sunset Cove Condo complex just 2 blocks off of Broadway & overlooks Crandalls Bay. Enjoy your morning coffee with a spectacular view of the WI River & the adjoining bay. This central location provides easy access to the area’s many athletics venues, nightlife, dining, & shopping.

4.97 out of 5 average rating, 144 reviews

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

4.98 out of 5 average rating, 145 reviews

Home in Lake Geneva

Updated luxury country getaway short walk to lake!

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

4.88 out of 5 average rating, 106 reviews

Cabin in Fort Atkinson

Cozy Lake Cottage With The Best View & Pontoon!

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

4.88 out of 5 average rating, 126 reviews

An indoor swimming pool is showcased, featuring a spacious layout with multiple lanes marked by floating lane dividers. The high, wooden-beamed ceiling allows natural light to filter in. Surrounding the pool, several lounge chairs are positioned for relaxation.

Cabin in Galena

Serenity Cabins - A rustic, yet upscale cabin!

Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities while feeling the rustic atmosphere. You can fall asleep with the sounds of nature and the whispers of the winds. Go for quiet walks as you surround yourself by nature's natural beauty or unwind in front of the fireplace.

4.92 out of 5 average rating, 158 reviews

Home in Galena

DunPuttin Place

Nestled on a secluded hillside that overlooks miles of Galena Territory's wildlife preserve, DunPuttin Place offers its guests total privacy, yet the convenience of being only minutes from the area's many popular amenities. DunPuttin Place is not just another carbon copy resort rental. It is a unique private home that has many features seldom found in vacation rentals. It has been tastefully designed and decorated to comfortably accommodate up to 12 guests of all ages.

4.97 out of 5 average rating, 474 reviews

A welcoming porch area is featured, equipped with two chairs and a small table. A sliding glass door leads into the condo, while a wall sign indicates the unit number. Lush green surroundings and lake views are visible in the background.

Condo in Wisconsin Dells

COZY, Lakefront, Fireplace, Free Kayaks

Relax on the porch and watch the boats glide by, soaking in the serene lake views. Whether you're looking for relaxation or recreation, our condo offers the best of both worlds. Book your stay today and experience the ultimate lakeside escape! Resort-Style Amenities • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • Proximity to numerous restaurants and activities • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

4.84 out of 5 average rating, 282 reviews

A contemporary shower area is highlighted with a textured stone wall, featuring neutral grey tones. The shower controls are mounted on the wall, and a light-colored tile floor extends throughout. A door is visible in the background, transitioning to another space.

Condo in Wisconsin Dells

Williamson Family Condo at Lighthouse Cove

NO SMOKING Upgrade to our Noah's Ark package after booking! Williamson Family Condo II is recently updated and located in Lighthouse Cove on Lake Delton in the heart of the Dells. Enjoy beach access, in & outdoor pools w/ hot tubs, and convenient parking. This condo is great for a couples or families. Let the older kids wander to and from Noah's Ark or go fishing at the lake while you take a much-deserved time out. Inquire about using our boat slip.

4.88 out of 5 average rating, 146 reviews

A serene waterside view is captured, featuring a calm inlet reflecting nearby homes and trees. The scene showcases several boat docks along the water, lined with a mix of boats and recreational equipment, surrounded by lush trees and clear blue skies.

Home in McFarland

Lovely Waterfront Two Bedroom House

Lovely two bedroom, one bath in a rural residential area of McFarland on inlet that connects to Yahara River and Lake Kegonsa (house is not directly on lake or river). The home is situated next to a charming campground and marina in nature. Walkable fishing areas. Lake Kegonsa State Park Trail is nearby for walking or snowshoeing. Just a 20 minute drive to downtown Madison! NO PARTIES. You will be asked to leave if there is any party activity seen.

4.88 out of 5 average rating, 215 reviews

A cabin-style home is nestled among tall pine trees, illuminated by warm outdoor lights. An inviting deck is visible, furnished with seating. Large glass doors lead into the interior, showcasing a cozy atmosphere. The setting maintains a peaceful and serene ambiance.

Cabin in Wisconsin Dells

Lake-view 3-bedroom Cabin Home on Lake Delton

Our place is close to ALL Lake Delton, WI Dells Downtown attractions. You’ll love our place because of the views of lake & pine trees, quiet setting, brand-new remolded interior with upscale furnishings, high ceilings, and the cabin coziness. Our Large, cabin accommodates up to 8 people very comfortable at over 1600 sq. ft. Best Resort in Town!!! Family fun atmosphere with two sandy beaches & large swimming pool. Kids love to fish off the piers.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Madison vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Monthly stays

Lake access

Stay near Madison's top sights

Wisconsin State Capitol28 locals recommend

Olbrich Botanical Gardens30 locals recommend

Memorial Union Terrace23 locals recommend

State Street111 locals recommend

Henry Vilas Zoo21 locals recommend

The Old Fashioned6 locals recommend

Home rentals in Madison

5 out of 5 average rating, 131 reviews

A modern living area is furnished with a plush sofa, accent chairs, and a rectangular coffee table atop a geometric area rug. A flat-screen television is placed on a wooden media console. Natural light enters through large windows, illuminating the space.

Home in Janesville

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

4.97 out of 5 average rating, 137 reviews

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

Home in Galena

Hot Tub-Dog friendly-fire tables-pools

4.99 out of 5 average rating, 107 reviews

The exterior of the home features a light green facade with a metal roof. A welcoming porch is visible, furnished with white rocking chairs. Lush grass surrounds the house, and a large tree can be seen beside it, contributing to a peaceful countryside setting.

Home in Union Center

Charming country home - great vacation area.

4.95 out of 5 average rating, 101 reviews

A spacious dining area features a wooden table set for six, adorned with lace placemats and a floral centerpiece. The open layout leads to a cozy living room, highlighted by comfortable seating and large windows allowing natural light to brighten the space.

Home in Portage

Grandma's House: Spring is Springing!

4.98 out of 5 average rating, 142 reviews

The charming cape cod-style home features a peaked roof topped with a tower. Lush green grass surrounds the property, with blooming hydrangea shrubs framing the front. Large windows are adorned with green shutters, allowing for natural light to fill the interior.

Home in New Glarus

Holy Cow! New Glarus Guest Haus

4.93 out of 5 average rating, 157 reviews

A modern kitchen features exposed wooden beams and a spacious island with a large marble countertop. Red chairs are arranged around the island, complemented by stainless steel appliances and white cabinetry. Natural light filters in through the windows, enhancing the design.

Home in Madison

Doty ★ Walk to Everything -Hotel Quality- Downtown

4.84 out of 5 average rating, 130 reviews

A charming exterior showcases a single-story home with a gray facade and white columns on the porch. The front yard features well-maintained greenery, including shrubs and flowers, complemented by mulch beds. A spacious porch with seating is visible, inviting relaxation.

Home in Monroe

Home away from home, close to historic square

4.79 out of 5 average rating, 180 reviews

The inviting entryway showcases an open floor plan, with a view of the modern kitchen and dining area. Decor includes the word 'HOME' prominently displayed and a decorative plant on a console table. Warm lighting highlights the hardwood-style flooring.

Home in Wisconsin Dells

The Freedom House by Patriot Properties

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Cottage rentals in Madison

4.99 out of 5 average rating, 136 reviews

Cottage in Milton

The Cottage

4.94 out of 5 average rating, 117 reviews

The exterior of a charming cottage is depicted, featuring light gray siding and a welcoming front porch adorned with potted flowers. A well-manicured lawn and symmetrical hedges frame the path leading to the entrance. Trees provide a natural backdrop, with soft sunlight filtering through the leaves.

Cottage in Lake Geneva

Chic & Charming - walkable to everything!

4.96 out of 5 average rating, 224 reviews

A picnic pavilion is situated in a green grassy area, framed by trees and boulders. The calm water of the Wisconsin River is visible in the background, with a forested hillside rising beyond. A clear blue sky completes the tranquil setting.

Cottage in Poynette

Lake Wiscosnin Cozy Cottage

Cottage in Richland Center

A charming cottage, originally a feed mill, is nestled in the rolling hills of the Driftless area. Lush greenery surrounds the property, while a tranquil pond reflects the natural landscape, complementing the blue sky and gentle clouds above.

5 out of 5 average rating, 189 reviews

Beautiful 1 Bedroom Cottage Tucked Away in the Hills of the Driftless Area

4.89 out of 5 average rating, 291 reviews

A charming white cottage is surrounded by greenery, featuring a sloped roof and a prominent red chimney. A covered porch with white railings offers a welcoming entrance, while large windows allow natural light to fill the interior.

Cottage in Arena

Sugarland Farmhouse

4.97 out of 5 average rating, 154 reviews

The exterior of a green cottage is surrounded by trees, featuring a welcoming front porch with a swing. A small bistro table and two red chairs are visible, complemented by natural landscaping of gravel and stones.

Cottage in Baraboo

Cottage · Cottage · Relaxing Cottage near Devils L

4.9 out of 5 average rating, 155 reviews

An open front door leads to a view of the calm lake, framed by trees. A grassy path extends towards the water's edge, with a glimpse of the neighboring structures visible in the distance.

Cottage in Pardeeville

Lake View Retreat

4.91 out of 5 average rating, 206 reviews

A stone fire circle is surrounded by four teal chairs, set on a lush green lawn. The spacious grounds feature two cottages in the background, one with a wooden deck, while trees provide shade around the area.

Cottage in Lake Geneva

Dakota's Como Cottage

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Pet-friendly vacation rentals in Madison

4.85 out of 5 average rating, 127 reviews

The living room features laminate hardwood floors and bright windows that allow natural light to fill the space. A gray sofa is positioned next to a coffee table, with a cozy chair nearby. A round mirror and artwork add personal touches to the minimalist decor.

Home in McFarland

The little Green Birdhouse-McFarland/Monona

4.98 out of 5 average rating, 177 reviews

The entrance of the yurt is framed by warm, wooden double doors with decorative glass panels. A covered porch extends from the entry, blending harmoniously with the surrounding trees and natural scenery. A wood stove is positioned nearby for warmth.

Yurt in Cambridge

YurtSimple

4.84 out of 5 average rating, 135 reviews

A comfortable living area is presented with a dark sectional sofa, accompanied by a wooden coffee table. Natural light enters through large windows adorned with dark curtains, while a decorative clock and artwork add character to the space. A fireplace is also visible.

Townhouse in Galena

131 Plum Cove - 3 Beds, 3 Baths, Sleeps 8

4.89 out of 5 average rating, 125 reviews

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

Home in Galena

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

4.9 out of 5 average rating, 117 reviews

Sunset over the water is captured, with vibrant shades of orange reflecting on the surface. Silhouetted tree branches frame the scene, while hills are visible in the background under a softly clouded sky.

Guest suite in Poynette

Lake Wisconsin 2BR* GreatHiking nearby -Water View

4.95 out of 5 average rating, 100 reviews

The living area features a spacious gray sectional sofa paired with a large coffee table at its center. A stone fireplace is located on the far wall, complemented by large windows that allow natural light to fill the room. Warm tones enhance the inviting environment.

Home in Williams Bay

Don’s Bay Getaway

4.8 out of 5 average rating, 223 reviews

The living room features a large smart TV mounted above a cozy electric fireplace. Two modern sofas and a coffee table are arranged on polished wood floors. A pair of patterned armchairs provides additional seating, complementing the stylish decor.

Townhouse in Fitchburg

Clean, quiet & family-friendly Townhouse-14 people