Vacation rentals in Sullivan

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Top-rated vacation rentals in Sullivan

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Guest favorite

A spacious outdoor deck is featured, overlooking a lush green backyard. Visible are various plants and garden elements, along with a patio umbrella. Stairs lead down from the deck to the garden area, providing access to the vibrant surroundings.

Guest suite in Waukesha

4.97 out of 5 average rating, 29 reviews

Tucked Away

For those in need of a "home away from home" while on the road working or just passing though on your travels. This private, quaint backyard parking/entrance mini apartment located in Waukesha's "Historic District" is for you. Enjoy large outer deck as weather permits. Stairs are required outside to enter. Walking distance to lively downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital.

Guest favorite

Home in Oconomowoc

4.92 out of 5 average rating, 170 reviews

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Guest favorite

A winter scene shows a large, chalet-style building with white and dark wood accents set against a clear blue sky. Snow covers the ground, and snow grooming equipment is visible nearby, indicating winter activities in the area.

Apartment in Whitewater

4.95 out of 5 average rating, 110 reviews

Pet-Friendly Industrial 2 Bedroom Near UWW Campus!

This newly renovated two bedroom unit is conveniently located near UWW, Starin Park, and the Kettle Moraine! We are pet friendly! We are within walking distance to sports fields and UWW. Explore all that Whitewater has to offer with our personalized guidebook! Hike the Kettle Moraine, enjoy many local dining options and events, or shop your heart out. We are local hosts and strive to provide a five star experience! If your group is larger than 4, we have two other units in the same building.

Guest favorite

A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.

Cottage in Hartland

4.95 out of 5 average rating, 139 reviews

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

Top guest favorite

Apartment in Watertown

4.97 out of 5 average rating, 249 reviews

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

Guest favorite

The exterior of a Victorian home is shown, featuring a charming front porch supported by decorative columns. Lush greenery, including bushes and plants, surrounds the entrance, contributing to a welcoming appearance. Clear blue skies complement the crisp architectural details of the house.

Home in Watertown

4.93 out of 5 average rating, 164 reviews

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Guest favorite

The modern kitchen features a large granite countertop with seating for two. A small dining area is visible, along with a television mounted on the wall. Natural light fills the space through the windows, complemented by dark curtains, and a green plant adds a touch of greenery.

Townhouse in Waukesha

4.92 out of 5 average rating, 157 reviews

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

Guest favorite

Cabin in Fort Atkinson

4.89 out of 5 average rating, 117 reviews

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!

Guest favorite

A charming street scene in downtown Oconomowoc features a variety of architectural styles. Two-story buildings line the street, with shopfronts displaying large windows. A red storefront stands out among neutral-toned buildings. Traffic signals and parked cars are visible, contributing to the vibrant atmosphere.

Home in Oconomowoc

4.85 out of 5 average rating, 75 reviews

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

Guest favorite

This log cabin is surrounded by greenery, showcasing natural stone accents and wooden details. A spacious deck features multiple hanging flower baskets, and stairs lead up to the entryway. The gently sloping driveway is lined with mulch and provides access to the cabin entrance.

Home in Dousman

4.96 out of 5 average rating, 161 reviews

Meracle Acres

Secluded among 50 acres of dense forest, stunning walking trails, wildlife and natural ponds, this one-of-a-kind log cabin is the perfect place to unplug and unwind. Whatever you’re looking for, you can find it all in this beautiful and tranquil getaway. Weekenders can enjoy hiking and exploring the gorgeous nature trails. The log cabin features a custom made bar, vaulted ceilings, a sauna room and outdoor hot tub with gorgeous views of the wildlife that surrounds.

Top guest favorite

The image showcases the exterior of the Green Door Cafe, characterized by a charming brick facade and large windows. A small outdoor seating area with tables and chairs is visible under leafy trees, providing a shaded, inviting space for guests.

Apartment in Delafield

5 out of 5 average rating, 41 reviews

Luxury Delafield Retreat | Walk to Lake & Shops!

⭐ 5-Star Comfort | Prime Location |Historic Downtown| Self Check-In ⭐ Welcome to Your Ultimate Delafield Getaway! Nestled in the heart of Historic Downtown Delafield, this luxury apartment is steps from Lake Nagawicka, top-rated restaurants, boutique shops, and scenic parks. Designed for both relaxation and adventure, this stylish retreat offers modern comforts, high-end finishes, and a perfect location for exploring everything Delafield has to offer.

Top guest favorite

The front view of a rustic stone cabin is framed by lush green trees. The structure features a wooden overhang supported by sturdy columns, with large windows allowing natural light to fill the interior. A neatly stacked pile of firewood is visible at the base.

Cabin in Whitewater

4.95 out of 5 average rating, 339 reviews

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.