Holiday rentals with a pool in Oshkosh

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

Water's Edge Cottage @ Evergreen Campsites&Resort

Welcome to Waters Edge where you will feel right at home in this bright contemporary home! Our spacious home and the best deck in the resort will be sure to delight your family and friends. This pet free cottage features 2 bedrooms and 1 spacious bathroom perfect for your family getaway in any season. During the summer months you will be able to use all the resort's amenities and during the winter cozy up next to the fireplace after spending the day at the local ski and tubing hill.

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

The Rabbit Retreat #1

Relax at Kilby Lake Campground in our beautiful log cabin, the Rabbit Retreat. This camping cabin is a perfect transition to camping; rustic enough to immerse yourself in the outdoors without the hassle of sleeping on the ground in a balmy tent! Share in our nature-centric campground and wander through the tranquil woods. If you desire more action, head to the playground, play a game of cornhole, paddle around the lake, or lounge in our heated pool that is open seasonally.

3bed lake house, private pool near WI Dells

Relax with the whole family at this peaceful pool lakeside home. If you enjoy kayaking, paddle boating, fishing/ice fishing or taking a dip in a pool then this place is for you! This home offers so many activities for the whole family to enjoy. Relax on the wrap around house deck with it’s own fireplace, grill, outdoor dinning or lounge area. Looking for a little more activity, head over to the pool deck, basketball court, or challenge your family to a yard game.

Touchdown Retreat – Indoor Pool, Hot Tub & Games!

Touchdown Retreat – Indoor Pool, Hot Tub & Games! Unmatched entertainment awaits at this 6,500 sq. ft. retreat just 5 miles from Lambeau Field! Enjoy a heated indoor pool 🏊‍♂️, hot tub ♨️, movie theater 🎬, and epic game rooms 🎯🎮 with air hockey, arcade games, and more. Six spacious bedrooms, brand-new furnishings, and a private fenced yard with a fire pit. Perfect for families & game-day getaways! Book now for the ultimate Green Bay experience! 🚀

A Sweet Suite in Freedom! Country Comfort!

Visiting friends or family in Freedom? Why bother them for an air mattress when you can stay right in town!? Going to a Packer Game and looking for a comfy place to stay with a super short drive? Found it! Ask about using the game room, golf simulator, or pool while you're here too! There's not a FULL kitchen!! Just one burner, and a flat griddle. There's also a microwave and small refrigerator/freezer, but overall, it's a suite. We think you'll LOVE it!

Sunny Days Await | Private Pool & Hot Tub Retreat

Looking for a relaxing summer escape? Whether you're here to explore or soak in the hot tub, you've found the perfect place to call home! ➤ Best for large groups and families ➤ Jacuzzi Spa w TV ➤ Outdoor smoker/grill combo ➤ Private Pool ➤ Dedicated Workspace | Fast wifi ➤ Outdoor Lounging & Bar with mini fridge ➤ Fully finished basement w/ 75" TV & bar! ➤ 2 Cozy indoor gas fireplaces (+ 3 outdoor) ➤ Fully Equipped Kitchen ➤ Local cafe & food mins away

Hickory on the LakeWaterfront Luxury on Winnebago

Welcome to "Hickory on the Lake," a meticulously renovated 3-bedroom, 3-bath sanctuary on Lake Winnebago. Indulge in the beauty of stunning sunrises and sunsets from the four seasons room. Nestled in a quiet, family-oriented neighborhood, this centrally located property provides easy access to Oshkosh's attractions. Immerse yourself in sophistication and create unforgettable moments against the backdrop of Lake Winnebago's breathtaking scenery.