Vacation rentals in Oconomowoc

4.85 out of 5 average rating, 133 reviews

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.

4.97 out of 5 average rating, 348 reviews

Apartment in Cedarburg

Cedarburg 2 br Apartment on prime Washington Ave

Prime location in Historic Cedarburg on Washington Ave in the heart of it all in a 2br apartment w/NO CLEANING FEE(short to do list at checkout).Guests get special attention that they deserve in a stylish calm space, above a 3 car garage accessed by stairs set back off of the street for a quiet timeout. So much to do & see or simply take a walk/picnic in the park. Just steps to shops, restaurants, wineries, & breweries set back off the street. Close to bike/hike trails, golf, museums, parks...

4.98 out of 5 average rating, 206 reviews

Condo in Lake Geneva

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

4.97 out of 5 average rating, 234 reviews

Condo in Racine

Gorgeous Main Street Apt with Lake Views (APT2)

Gorgeous, open concept Main Street apartment on 3rd level, with views of downtown and partial views of the lake and harbor. New mini kitchen with 2 induction stove top burners, a microwave, toaster, and all the cookware and utensils needed for a getaway. Supersize custom island, comfy furnishings, and convenient to everything downtown. Unique building is connected to parking garage. Drive up to the 3rd floor - walk just 10 steps to your door - enjoy the views from above, without the climb.

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

4.97 out of 5 average rating, 141 reviews

Bungalow in Lake Geneva

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.

4.98 out of 5 average rating, 144 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.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

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

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."

4.9 out of 5 average rating, 147 reviews

Home in West Allis

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

4.96 out of 5 average rating, 187 reviews

Home in Oostburg

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

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What guests are saying

Tiny Red House on Lake Delavan

4.98 out of 5 average rating, 54 reviews3 weeks ago

We hardly know where to begin! Originally, we chose this place as a little escape from the city and a spot for our pup, Roo, to run and explore. However, The Tiny Red House far exceeded our expectations in every way! To start, the yard was absolutely perfect. On top of that, the area is filled with beautiful, dog-friendly trails, making it an ideal getaway for nature lovers. As for the house itself—it was by far the most well-stocked Airbnb we’ve ever stayed at! No other rental even comes close. We also fell in love with the location—close enough to the lake for convenience yet peacefully tucked away for privacy. To say we had a great time would be an understatement! Thank you for such a wonderful stay! We truly appreciate the thought and care that went into making this place so special.

Tiny home in Delavan

What guests are saying

1 block to the Lake, then 2 blocks to Downtown

4.95 out of 5 average rating, 44 reviews1 month ago

If every host could be like Ryan and Angela - this app would be a much better place. They were extraordinarily communicative, attentive and eager to ensure all needs were met. The house was perfect (with a lot of character) - and is a couple of blocks away from the lake and lake trail. Also very close to downtown (for those who don’t mind the walk). Overall, this house is perfect for families looking to create long lasting memories and is managed by hosts that will go out of their way to make it so.

Home in Lake Geneva

What guests are saying

Cozy Cottage by the Lake! Kayaks! Paddleboard! Wow

5 out of 5 average rating, 5 reviews2 months ago

This cottage was wonderful to stay at! Very cozy! Great to stay at in winter as an indoor getaway and this would be an awesome stay in the summer. I passed up the place at first when I arrived because I didn't think it would be that nice of a place! Rainfall shower was nice and great areas to sit and chill out. I would definitely stay here again!

Home in Salem

What guests are saying

Pet-Friendly Slice of Heaven by Lake Geneva & Como

4.97 out of 5 average rating, 33 reviews1 week ago

We truly enjoyed our stay at Joe and Nadine's place! The house was beautiful, spotless, and relaxing. It was the perfect place to unwind. The location was close to restaurants and activities around Lake Geneva, Lake Como, and surrounding towns such as Delavan and Elkhorn. Joe and Nadine were wonderful hosts- providing ideas for things to do/see in the area, as well as providing great restaurant recommendations. They were also super quick to respond and really seemed to want to make sure we enjoyed our stay. If you're looking for a relaxing reprieve and a sparkling clean space with all you need to feel at home, look no further!

Home in Lake Geneva

What guests are saying

The Beach house! Enjoy Beachfront Living!

5 out of 5 average rating, 26 reviews3 months ago

MIke was an amazing host. Extremely responsive, and very flexible and accommodating. Was in town with my family for a funeral; Mike was very understanding and was willing to go the extra mile to support the changing flow of the trip. Beautiful view; I could imagine it would be amazing in the summer. All-in-all, a great stay, and exactly what we needed during this time. Would love to be there in the summer or fall!

Home in Racine

What guests are saying

Huge! Sleeps 12, Perfect getaway for a large group

4.96 out of 5 average rating, 79 reviews3 months ago

Beautiful home with ample space for our group of 10! It was our first Christmas without my mother and we decided as a family to spend our holiday somewhere new. The owner of the house made sure we had everything we needed and went over and beyond to make the house look festive! Despite it being winter, there were a lot of things to do. We made use of the beautiful game room, played cards, board games, shot pool and had our daily movie night in one of the two large family rooms. We had such a great experience despite my family’s loss that we are thinking of returning next year!

Home in Lake Geneva

What guests are saying

The Cottage on Warren, Downtown, Backyard Fire Pit

5 out of 5 average rating, 14 reviews7 months ago

Our family had a wonderful time here. Close enough to walk to restaurants or the path around the lake, but in a very quiet neighborhood that made you feel at home. The host was quick to respond when we had a question. The house was beautiful and I wish my house was as clean! I hope we have the opportunity to come back and stay here again.

Home in Lake Geneva

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Popular amenities for Oconomowoc vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Oconomowoc's top sights

Weissgerber's Golden Mast Inn8 locals recommend

Bella Gusto Restaurant And Italian Market & Pizzeria7 locals recommend

Foolery's5 locals recommend

Piggly Wiggly5 locals recommend

City Beach5 locals recommend

Roots Coffeebar & Cafe5 locals recommend

Other great vacation rentals in Oconomowoc

Superhost

4.93 out of 5 average rating, 15 reviews

Large Geneva Home | 8 beds | Fenced Yard Walkable

4.85 out of 5 average rating, 20 reviews

Guest suite in Wind Lake

Secret Garden Getaway

4.93 out of 5 average rating, 101 reviews

Home in Lake Geneva for your whole family

Superhost

Home in West Allis

4.77 out of 5 average rating, 153 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

4.91 out of 5 average rating, 114 reviews

Lake Geneva cottage with private beach access

4.92 out of 5 average rating, 344 reviews

Cabin in Trevor

Living the Lakehouse Dream

5 out of 5 average rating, 20 reviews

Condo in Fontana

Abbey Villa Getaway |Patio | Pool | Walk to Water