Holiday rentals in Illinois

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Top-rated holiday rentals in Illinois

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Cobden

4.93 out of 5 average rating, 60 reviews

Wine trail, views, hot tub, pool…

Escape your worries in this spacious, serene retreat. Whether your exploring the local wineries, embarking on a girl’s trips, hiking scenic trails, enjoying a family vacation, or even casting a line on a fishing trip, our home is the perfect destination. After a day of adventure, unwind in the comfort of our well-appointed space. End your day by the pool, soak in the hot tub, or enjoy a campfire. Located just a short distance from Bald Knob Cross. Cameras actively recording at all times.

Guest favourite

Home in Havana

4.95 out of 5 average rating, 125 reviews

Private Beach • Lakefront • Kayaks • Sunsets

The Havana Cabana is your home away from home. Take time to breathe and just be by soaking in your surroundings and being with the people that matter most. We strive to provide you with a relaxing atmosphere and great amenities. You will have full access to your own private, sandy beach (directly behind the home) with amazing sunset views and great fishing. We provide 3 adult kayaks, one double and one child (under 150 pounds), and a pedal boat. Great outdoor fire-pit for s’mores and memories.

Guest favourite

Cabin in Savanna

4.98 out of 5 average rating, 49 reviews

River Rail Retreats Blue Cabin at Palisades

Welcome to River Rail Retreats at Palisades! (formerly The Nest at Palisades) Down a private lane, nestled amidst 5 acres of woods, you'll find 3 Cabins available to rent. The Property & Cabins have undergone New Ownership and extensive remodeling, with brand new furnishings, appliances, & decorations. While located in a country setting, you are still close to Downtown Savanna, Mississippi River, & Palisades State Park. This is a perfect retreat for a blend of tranquility and rustic charm.

Top guest favourite

Home in Freeport

4.98 out of 5 average rating, 176 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Superhost

Townhouse in Galena

4.96 out of 5 average rating, 23 reviews

Cozy Sunrise Villa!

1 bedroom, 2 bath townhome with main floor living room, dining room, wall scrabble board, kitchen, full size sofa sleeper, laundry room, gas fireplace. Upper floor has king bedroom with full bath. Back deck off main level. Access to private Walnut Hill pool. Resort amenities include indoor/outdoor pool, game room at Owner's Club, lounge area, tennis, golfing, hiking, walking trails, basketball court, marina for boat rental and fishing, horseback riding. Only 6 miles to downtown Galena.

Top guest favourite

Townhouse in Galena

5 out of 5 average rating, 16 reviews

Perfect Getaway: Newly Renovated

Take it easy at this unique and tranquil getaway. Relax with a few friends at this peaceful place to stay. Located in the Galena Territories, this rental provides something for everyone. During the summer months you can access trails, golfing, an indoor and outdoor pool and so much more. During the winter months you are close to one of the finest ski resorts around. In Fall, access breath-taking views of trees as they change color. All year round there is something to look forward to!

Top guest favourite

Home in Galena

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.

Top guest favourite

Home in Galena

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.

Guest favourite

Bungalow in Fairfield

4.97 out of 5 average rating, 103 reviews

Davis House

Very nice, recently remodeled Home in Fairfield. One bedroom with one and a half bath. The master bed is a king and amazingly comfortable. The Master bath is straight out of a magazine, tile shower, double vanity, and plush towels. The living room couch is a queen pull out. It's as comfortable as a hide a bed couch can be. Completely stocked down to coffee on us! Great location- midway down Main Street. Perfect central location.

Superhost

Home in Fox Lake

4.87 out of 5 average rating, 124 reviews

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

Guest favourite

Home in Petersburgh

5 out of 5 average rating, 5 reviews

Top-Rated- Modern Getaway

Experience the ultimate in comfort and style: This premier three-bedroom home is the perfect retreat, boasting a master bedroom with a plush king bed and two inviting bedrooms with queen beds. Each room is tastefully decorated, offering a cozy and welcoming atmosphere. Whether you're here for a weekend or a longer stay, this property promises a comfortable and inviting experience.

Guest favourite

Home in Galena

4.9 out of 5 average rating, 20 reviews

A&D Rise Getaways @ Oak Glen Retreat

Welcome to A&D Rise Getaways @ Oak Glen Retreat, a cozy and well-appointed 2-bedroom, 2-bathroom townhome nestled along the South Course in The Galena Territory. With wooded views, vaulted ceilings, and a two-story great room, this home offers the perfect balance of comfort and character—just 10 minutes from downtown Galena’s shops, restaurants, and charm.