Vacation rentals in Cortland

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Top-rated vacation rentals in Cortland

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

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Top guest favorite
A cozy living area features a deep-seated leather couch and a reclining chair, surrounded by bookshelves filled with antique books. A coffee table sits in front of the fireplace, which casts a warm glow. Large windows offer natural light, with a small dining table for four nearby.
Home in DeKalb
5 out of 5 average rating, 44 reviews

The Gurler House

Welcome to Downtown DeKalb’s most charming and highly-rated historic stay! This beautifully restored home offers both modern comfort and vintage charm. The Gurler House, built in 1857, is on the National Register of Historic Places. This lovingly updated home sits back in a gorgeous park-like setting surrounded by nature. While nestled in a peaceful neighborhood, it is only 2 blocks from the Egyptian Theatre and all the downtown shops and restaurants and only a couple minutes away from NIU.

Top guest favorite
Treehouse in Schaumburg
4.94 out of 5 average rating, 866 reviews

Enchanted Garden Treehouse (Amenity*)

Spring is here, the flowers out, the treehouse warm and cozy, and the hot tub ready! Relax on cool evenings in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall cuts thru snow into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

Top guest favorite
A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.
Farm stay in Cherry Valley
4.97 out of 5 average rating, 447 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Top guest favorite
A hot tub is positioned on a deck overlooking a scenic river view. The water's surface reflects soft light, creating a serene ambiance. A lattice privacy screen is visible in the background, framing the peaceful outdoor setting.
Home in Rockford
5 out of 5 average rating, 141 reviews

Adults Only "Red Room" Home with Hot Tub

Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Top guest favorite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 253 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favorite
Apartment in Sycamore
4.96 out of 5 average rating, 78 reviews

Hidden Gem of Sycamore

Keep it simple at this peaceful and centrally-located place. Located just 3 blocks/5 minute from downtown. Walking distance to Blumen Gardens and The Regale Center. Apartment is above garage in the historic district of Sycamore. Private laundry room is available to guests and free of charge. If you’re coming for the car show in July we are just 1 block from where the car display starts. Sycamore Steam Show is approximately 7miles/15 minutes. City park is 1 block from apartment.

Top guest favorite
Loft in West Dundee
4.96 out of 5 average rating, 407 reviews

124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #1, a one-bedroom space featuring exposed brick, timber ceilings, and clean finishes that feel both character-driven and easy to enjoy. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.

Top guest favorite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.93 out of 5 average rating, 112 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top guest favorite
A spacious kitchen features warm wooden cabinetry and granite countertops. Four high-backed stools are positioned at the kitchen island. Modern appliances, including a stainless-steel stove and microwave, are present. Soft pendant lights illuminate the area, creating a functional and inviting cooking space.
Home in DeKalb
5 out of 5 average rating, 47 reviews

Luxury Home Away from Home

When you arrive, you will immediately feel at home. Take off your shoes and relax. Tastefully decorated without clutter. Hickory hardwood floors and custom woodwork abound! Owners pride themselves on creating an atmosphere exceeding your expectations. Owners have stayed at many short-term rentals and hope their experiences will create your stay to be memorable and worry free.

Top guest favorite
Home in DeKalb
4.91 out of 5 average rating, 254 reviews

Country charmer 1885 vintage farmhouse near NIU

Spacious 1850’s country home on 5 acres. 4 miles from NIU. Ten minutes from Blumen Gardens, Chapel in the Pines, and Aquaviva Winery. Kitchen has all cooking utensils. Plenty of free parking, Handicap accessible entry. Property offers fire pits, decks, charcoal grills, outdoor games, picnic tables. Stunning view country landscape. Not corporate owned.

Top guest favorite
A log home is set against a bright sky, featuring a spacious covered porch with wooden railing and several potted plants. Large windows flank the entrance, while natural stone accents the chimney. A grassy area surrounds the home, enhancing its tranquil ambiance.
Home in Geneva
4.94 out of 5 average rating, 124 reviews

New Modern Log Home Retreat in the Heart of Geneva

Located minutes from bustling downtown Geneva, this authentic log home is nestled on a quiet residential street on a nature filled half acre. Built in 2007, this home will be yours to use as a homebase for downtime or as you explore the many sights, eateries, and shopping of Geneva and the surrounding area.

Top guest favorite
A covered outdoor living space features a large dining table surrounded by soft lighting from hanging bulbs. Potted greenery adds a vibrant touch, while natural stone accents enhance the atmosphere. The space is designed for relaxation and socializing, with an inviting layout.
Cottage in Fox River Grove
4.97 out of 5 average rating, 110 reviews

Little Fox Cottage - A Cozy Riverview Getaway

A cozy getaway in the Northwest Suburbs of Chicago. Located 40 miles from the city and just 1.25 miles from the Fox River Grove Metra stop. Get away from the city or 'work from home' in our 1 bedroom cottage with a giant covered outdoor space tucked against the slope of a beautifully terraced hill.

Popular amenities for Cortland vacation rentals

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