
Holiday houses in Jackson
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Top-rated holiday rentals in Jackson
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Bark Lake, Entire Home, Private Lake Frontage 50ft
A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.
4.88 out of 5 average rating, 534 reviews
Perfect Balance in Cedarburg Gem
This spacious, private studio apartment offers a perfect blend of serenity and activity. Situated at the back of a 1.25 acre lot, beyond the lovely 1862 stone farmhouse it overlooks, the carriage house is a peaceful getaway -- minutes from all that bustling historic Cedarburg has to offer. Just .4 mile from the OZA Fairgrounds and .8 mile to downtown shops and restaurants, it's a quick drive or an easy walk to many amenities. Relax on the balcony before or after a day of fun sightseeing. Cheers!
4.99 out of 5 average rating, 115 reviews
Peaceful weekend or extended stay, full amenities
The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.
4.95 out of 5 average rating, 306 reviews
Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.
4.92 out of 5 average rating, 221 reviews
Lake Michigan Beach Home by Frank Lloyd Wright pro
Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.
4.96 out of 5 average rating, 184 reviews
hot tub and sauna on 5 private acres
Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!
5.0 out of 5 average rating, 286 reviews
Charming duplex walkable to historic downtown
Location is key to an enjoyable getaway. The Hilburg House, a quaint 1912 updated farmhouse with two units, is located in a quiet neighborhood around the corner from several parks on Cedar Creek. A short 10-minute walk to town and you will find an abundance of boutiques, coffee shops, restaurants, local brew pubs, art museum, and cultural center. The park offers weekly music performances in summer and offers 4 dedicated pickleball courts with friendly drop-in sessions.
4.98 out of 5 average rating, 101 reviews
Private 3 bedroom lake house
A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.
4.85 out of 5 average rating, 121 reviews
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.
4.88 out of 5 average rating, 145 reviews
Mequon Ranch Experience
Escape to our stunning vacation home in Mequon, WI for a peaceful group getaway. Completely renovated and fully furnished, our home comfortably accommodates up to 8 guests. Enjoy complete privacy on our one-acre lot, and relax on the patio, grill up a delicious meal, or gather around the fire pit. Only blocks away from the Milwaukee River and minutes to downtown Mequon, our home offers easy access to nearby attractions. Book now for an unforgettable stay!
4.88 out of 5 average rating, 226 reviews
Our Happy Place in Cedarburg
You are certain to enjoy a special gathering with family or friends at Our Happy Place. Three bedroom / two bathroom single family home has all the conveniences of home. The property is just a one block stroll from many of the unique festivals held in historic downtown Cedarburg. Three wineries, numerous restaurants, coffee shops and fun shopping all within short walking distance. Friendly, safe neighborhood with quiet sleeping areas inside.
4.98 out of 5 average rating, 243 reviews
Delightful 1 Bedroom in Downtown West Bend.
Private space in upper of established business. Fully furnished apartment with amazing sun light. Friendly, comfortable space that offers restaurants, bars and great dining all just steps away. Includes Overnight Parking Pass for entire stay. Side entrance with coded door for privacy. Close to nature trail for hiking or biking. All baking, cooking, utensils, dishes included.
4.94 out of 5 average rating, 140 reviewsPopular amenities for Jackson holiday rentals
Other great holiday rentals in Jackson

Peaceful Home with Fenced Yard - Country Aire
4.93 out of 5 average rating, 28 reviews
The Pike Lake Cottage House
4.92 out of 5 average rating, 53 reviews
Grafton Getaway – Spacious Side-by-Side w/Fire Pit
4.88 out of 5 average rating, 72 reviews
Lovely 2 bedroom upper near downtown
4.93 out of 5 average rating, 28 reviews
Cold Springs 1855 Log Cabin
5.0 out of 5 average rating, 17 reviews
Washington Suite | Downtown Cedarburg|Main St View
5.0 out of 5 average rating, 32 reviews
Little Red House
5.0 out of 5 average rating, 40 reviews
Peaceful 3 Bed home w/ Farm View by Lake Michigan
4.67 out of 5 average rating, 175 reviewsDestinations to explore
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- Kohler-Andrae State Park
- Alpine Valley Resort
- Baird Center
- Whistling Straits Golf Course
- American Family Field
- Milwaukee County Zoo
- Milwaukee Public Museum
- Marquette University
- Riverside Theater
- Bradford Beach
- Fiserv Forum
- Holy Hill National Shrine of Mary
- Blackwolf Run Golf Course
- Pabst Mansion
- Wisconsin State Fair Park
- South Shore Park
- Mitchell Park Horticultural Conservatory
- Discovery World
- Betty Brinn Children's Museum
- Atwater Park
- Lake Park
- Racine North Beach
- Little Switzerland Ski Area
- Lion's Den Gorge Nature Preserve





