Vacation rentals in Middleton

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.

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.

4.83 out of 5 average rating, 231 reviews

*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.

4.88 out of 5 average rating, 105 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!

4.98 out of 5 average rating, 146 reviews

An outdoor fire pit surrounded by wooden benches and chairs is visible in a spacious green area. The cabin in the background features a red exterior and large windows framed by trees, offering a serene spot for gathering.

Home in Elkhorn

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."

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.

4.97 out of 5 average rating, 473 reviews

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

A spacious living area features comfortable seating and a central coffee table. A stone fireplace is positioned against the wall, and a large flat-screen TV is mounted above it. Light streams in through windows framed with rich curtains, enhancing the inviting atmosphere.

5 out of 5 average rating, 10 reviews

Charming 2-Bedroom, 2-Bathroom in Chula Vista

Welcome to your perfect getaway in Chula Vista, Wisconsin Dells! This charming 2-bedroom, 2-bathroom rental offers the ideal blend of comfort and convenience, making it the perfect home base for your vacation adventures. The spacious living area is perfect for relaxation, featuring comfortable seating, a pull-out sofa, and not one but two cozy fireplaces to warm up after a day of exploring. The fully equipped kitchen has everything you need to prepare meals.

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.

4.84 out of 5 average rating, 282 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.

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.

4.97 out of 5 average rating, 171 reviews

Home in Wisconsin Dells

*Luxurious Turkey Run*

Turkey Run is a beautiful, welcoming home that we can't wait to share with you. From top to bottom, you'll find attention to detail; comfy beds, warm, relaxing decor and a great pool table and media room to relax. Wisconsin Dells has so much to offer, but you'll really appreciate coming home to this private haven just a couple of minutes out of town. Turkey Run gets it's name from the wild turkeys that roam the property and adjoining fields.

Cottage in Fontana-on-Geneva Lake

A serene lakeside scene captures a sandy beach area bordered by manicured greenery. Boats are anchored in the water against a backdrop of a colorful sunset, with the sky displaying hues of orange and pink. A stone pathway leads towards the waterfront.

4.98 out of 5 average rating, 104 reviews

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

4 Bedroom 2 1/2 bath vacation cottage in Abbey Springs Resort Community on Lake Geneva. Resort Pass is required for all guests (included) and gives entry to the resort plus indoor and outdoor pool (Memorial to Labor Day), hot tub, games room , gym, tennis courts , pickle ball. 2 restaurants beach and fire pit on site. Newly Renovated Golf Course not included but available by paying at club house . We welcome all .

4.93 out of 5 average rating, 250 reviews

An outdoor gathering area is set among tall trees, featuring large wooden picnic tables and a pair of swinging chairs attached to a wooden frame. A rustic cabin is visible in the background, surrounded by fallen leaves.

Home in Wisconsin Dells

Charmed Lodge. Sauna. Games & lots of charm

Wisconsin Dells premier vacation rental! Sleeps 16! Less than 10 minutes to all major resorts and Dells attractions! Plenty Of Amenities! Fireplace in living room and basement, large deck, outdoor fire pit, Jacuzzi in basement, sauna and games. 3 levels. Plenty of space for large family gatherings and groups! Very peaceful and quiet. Golf/waterpark/Dells Trolley tickets available at a discounted rate!

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Popular amenities for Middleton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Middleton's top sights

Walgreens30 locals recommend

Whole Foods Market6 locals recommend

Pasqual's Hilldale9 locals recommend

Other great vacation rentals in Middleton

4.92 out of 5 average rating, 189 reviews

The image features a serene view of the Wisconsin River framed by lush green trees and a well-maintained lawn. Canoes are visible along the water's edge, with sandy banks and distant hills providing a picturesque backdrop under a clear blue sky.

Home in Poynette

Island View Hideaway-Peaceful, On Water, Sandbars!

Apartment in Wisconsin Dells

An indoor waterpark features multiple water slides, including a pair of wide, blue slides leading into a splash pool. Guests of various ages enjoy swimming in the adjacent lazy river and engaging in water play, surrounded by tropical-themed decor and splashing water.

5 out of 5 average rating, 8 reviews

Chula Vista Resort Condo

4.94 out of 5 average rating, 72 reviews

A spacious cabin is pictured against an expansive lawn, surrounded by verdant trees. A stone chimney rises prominently against the sky, which is covered with a mix of soft clouds and a hint of sunlight. The serene landscape evokes a sense of tranquility.

Cabin in Merrimac

Enjoy sunsets at a fully equipped & secluded cabin

4.89 out of 5 average rating, 249 reviews

Home in Argyle

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

4.99 out of 5 average rating, 107 reviews

A wooden staircase leads to the second floor, featuring polished steps and a handrail. The walls are lined with vertical wood paneling, and natural light enters through an open door at the top of the stairs. Comfortable seating is visible in the background.

Home in Union Center

Charming country home - great vacation area.

Cottage in Richland Center

A quaint cottage with a wooden exterior stands amidst lush greenery, framed by a clear blue sky. A paved pathway leads to the front door, bordered by neatly arranged flower beds and shrubs, inviting visitors to explore the surrounding landscape.

5 out of 5 average rating, 189 reviews

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

An aerial view shows a vibrant outdoor pool area featuring a winding water slide and a separate lazy river. Sun loungers are arranged around the pool, while shaded seating is provided under red umbrellas. Lush greenery surrounds the recreational space, creating a lively atmosphere.

5 out of 5 average rating, 6 reviews

The Villa | 3BR Retreat for 14 w/ Whirlpool Tub