Holiday rentals in Middleton

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.

*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.

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.

Red Lodge - Game Room, Hot Tub, Near Lake

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."

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.

Perfect Getaway: Newly Renovated

Take it easy at this unique and tranquil getaway. Relax with a few friends at this peaceful place to stay. Located in the Galena Territories, this rental provides something for everyone. During the summer months you can access trails, golfing, an indoor and outdoor pool and so much more. During the winter months you are close to one of the finest ski resorts around. In Fall, access breath-taking views of trees as they change color. All year round there is something to look forward to!

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

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.

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.