Holiday rentals in Madison

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Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Juneau

4.85 out of 5 average rating, 130 reviews

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.

Guest favourite

Home in Wisconsin Dells

4.93 out of 5 average rating, 233 reviews

Charmed Lodge. Sauna. Games & lots of charm

Timber Lodge Escape! Wisconsin Dells premier vacation rental! Sleeps 16! 5 minutes from Noah's Ark, 7 minutes to downtown Wisconsin Dells, less than 10 minutes to all major resorts and Dells attractions! Plenty Of Amenities! Fireplace in living room, large deck, outdoor fire pit, Jacuzzi in basement + games. 3 levels. Plenty of space for large family gatherings and groups! Very peaceful and quiet. Newly updated Golf/waterpark/Dells Trolley tickets available at a discounted rate!

Superhost

Apartment in Wisconsin Dells

4.82 out of 5 average rating, 224 reviews

*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo | Breathtaking Views | Downtown WI Dells

**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.

Guest favourite

Bungalow in Lake Geneva

4.97 out of 5 average rating, 138 reviews

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.

Guest favourite

Home in Lake Geneva

4.98 out of 5 average rating, 130 reviews

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.

Guest favourite

Home in Elkhorn

4.98 out of 5 average rating, 139 reviews

Red Lodge~Game Room, Hot Tub, Ski~Family Retreat!

Looking for a memorable Wisconsin vacation experience? The Red Lodge is the ideal blend of comfort and style. Super clean, fully stocked, with gorgeous outdoor green spaces and unique amenities, you'll love it here! Jeff - "The devil is in the details, and no detail is overlooked here." Kelsey - "We are obsessed! This is THE nicest Airbnb we've stayed in across the country.. There was something truly unique about each room." Alia - "Hands down the best Airbnb we have ever stayed in."

Guest favourite

Home in Lake Geneva

4.96 out of 5 average rating, 78 reviews

Huge! Sleeps 12, Perfect getaway for a large group

Pretend you are lost in a magical place as you curl up on the porch on a rocking chair. Then fall asleep in a heavenly bedroom in a luxurious king size bed. When you wake up, all your worries have faded away and the espresso machine awaits. This is Como! We designed the most heavenly home for you so the minute you step inside you're on vacation. Perfect for all seasons! Two living rooms, game room, 5 bedroom, 2.5 bath, stocked with everything we can think of to make your stay perfect.

Superhost

Cabin in Galena

4.88 out of 5 average rating, 126 reviews

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.

Guest favourite

Home in Lake Geneva

4.94 out of 5 average rating, 33 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

Superhost

Apartment in Wisconsin Dells

4.85 out of 5 average rating, 273 reviews

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.

Guest favourite

Cabin in Wisconsin Dells

4.88 out of 5 average rating, 210 reviews

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.

Guest favourite

Home in Lake Geneva

4.97 out of 5 average rating, 146 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!