Vacation rentals in Middleton

4.87 out of 5 average rating, 171 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.

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, 104 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."

4.82 out of 5 average rating, 293 reviews

Galena Retreat - Eagle Ridge Territories

The perfect place to relax and unwind in a wooded setting far away from the hustle of daily life. Short drive to downtown Galena for shopping and dining. Short drive to skiing and you can walk to the resort for dining and adult beverages. Indoor and outdoor swimming pool at the owners club along with other activities. 1 bedroom w/one queen, 1 bedroom w/two single beds, 2 full bathrooms, Kitchen, Living Room Dinning area, Screened Summer room, Fully equipped Kitchen, Cable TV and wifi.

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.

A spacious outdoor area showcases a well-maintained patio with stone pathways and seating arrangements. The property features a modern two-story structure with a welcoming entrance, surrounded by greenery and decorative landscaping. A grill is positioned nearby for outdoor cooking.

4.98 out of 5 average rating, 62 reviews

Jackson Ready Properties

Bring the whole family to this great place with lots of room for fun. Enjoy the patio or deck and cozy up to the outdoor firepit. Socialize with family and friends inside with two large living areas featuring plenty of seating and pool, foosball or wet bar to keep guests entertained. Three large bedrooms that sleep 6 comfortably as well as a sofa sleeper for kids or tag-along adults! Located within walking distance to the Owner's Club or a short cruise down the hill to the Marina.

4.92 out of 5 average rating, 157 reviews

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.

The lake view from the property features calm waters, with several boats docked along a wooden pier. A patio area is visible, furnished with seating and surrounded by well-maintained landscaping, providing a serene atmosphere for relaxation.

4.97 out of 5 average rating, 472 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 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, 281 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, 145 reviews

Three children sit closely on a wooden dock, facing a tranquil inlet lined with boats and shaded by overhanging trees. The calm water reflects the surrounding greenery, creating a serene atmosphere in the rural setting.

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.

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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

Hilldale Shopping Center63 locals recommend

Walgreens30 locals recommend

Whole Foods Market29 locals recommend

Pick 'n Save27 locals recommend

Willy Street Co-op—West25 locals recommend

Metcalfe's Market19 locals recommend

Other great vacation rentals in Middleton

5 out of 5 average rating, 56 reviews

An inviting outdoor deck is showcased, featuring two lounge chairs and a stone fireplace. A dining table is set for several guests, surrounded by trees and expansive views. Large windows allow natural light to flow into the cabin, enhancing the serene setting.

Cabin in Galena

Upscale*5KING Bed 5 Bath*Pets*Luxe Amenities*Views

4.91 out of 5 average rating, 188 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!

The spacious indoor pool area features a large swimming pool with clear blue water. A hot tub is positioned by the edge, with bubbling water visible. Adjacent seating is available along with lounge chairs, while large windows provide ample lighting.

4.84 out of 5 average rating, 55 reviews

YourBohoRetreat+FREE Waterpark Passes

4.89 out of 5 average rating, 19 reviews

A comfortable living area features a brown leather sofa, light wood furniture, and a large area rug. Natural light streams through multiple windows, while a flat-screen television is mounted on the wall above a modern fireplace. A dining table is situated nearby.

Townhouse in Galena

Townhome - Indoor Pool, Arcade, Hiking, Skiing

5 out of 5 average rating, 4 reviews

The spacious kitchen features wooden cabinetry and modern stainless steel appliances. An island with seating for four is highlighted by warm lighting. The open layout is complemented by rustic wood paneling and large windows, allowing natural light to fill the area.

Barn in Davis

Sunrise Country Views

A hot tub filled with bubbling water is situated under a wooden overhang. Snow-covered trees can be seen in the background, and the cozy surrounding adds a sense of relaxation to the space.

5 out of 5 average rating, 27 reviews

Modern spacious 4 bedroom retreat with 3 en-suites

An inviting living area features a stone fireplace with a flat-screen TV above, complemented by modern gray seating and colorful cushions. A dining space with a round table for six is visible in the background, with the fully equipped kitchen showcasing new appliances.

5 out of 5 average rating, 6 reviews

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