Vacation rentals in Cortland

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Top-rated vacation rentals in Cortland

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Top guest favorite

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Apartment in West Dundee

4.96 out of 5 average rating, 95 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Guest favorite

The exterior of a charming Barndominium is showcased, featuring a neutral color palette with a metal roof. The building displays large windows and a large garage door. Flower planters line the entrance, and well-maintained grass surrounds the structure, enhancing the rural ambiance.

Farm stay in Clare

4.89 out of 5 average rating, 63 reviews

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

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, 24 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

The exterior of the historic home presents a charming two-story structure with light-colored siding and dark shutters. A welcoming front door is framed by neatly trimmed hedges and stone steps. The setting features a well-maintained yard with trees and shrubs, creating a pleasant approach.

Home in Sycamore

4.97 out of 5 average rating, 39 reviews

The 1870 A Historic Downtown Sycamore Home

Welcome to the “1870” A historic home in Downtown Sycamore, IL. The whole group will be comfortable in this spacious and unique space. 4 Bedrooms, first floor master, living room, and 2 full bathrooms. Built in 1870 but full of modern charm. It is only 1 block to Historic Downtown Sycamore, IL. First floor requires no stairs and has a master with a full bath. 2nd floor is 3 bedrooms and a full bath. NO PARTIES are allowed at this home Only 7 miles to NIU. Walk to downtown sycamore.

Guest favorite

A cozy living area is furnished with a brown sofa adorned with decorative pillows. A small coffee table sits in front, complemented by a simple vase with dried flowers. The open layout reveals the kitchen and dining space in the background.

Apartment in Sycamore

4.9 out of 5 average rating, 10 reviews

Charming 1BR Apt in Sycamore

This charming unit offers the best of both worlds: a peaceful, quiet retreat that’s just steps away from the heart of the action. Conveniently located near major shopping centers and within walking distance to popular restaurants and local stores, you’ll have everything you need at your fingertips. Whether you’re here for business, shopping, or a weekend getaway, this location provides unmatched convenience and comfort. This unit is on the main level with easy parking access short steps away.

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, 395 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.

Guest favorite

A two-story barn-style structure is surrounded by lush green trees and manicured grass. The exterior features a combination of white siding and dark accents. A wooden deck and exterior stairs lead to the second floor, providing a welcoming entryway.

Barn in Elgin

4.96 out of 5 average rating, 26 reviews

Tranquility barn close to town

Discover the gorgeous natural landscape surrounds that this place has to offer . Close to town & all amenities About this space 2nd floor guest barn/ apartment , We offer 2 bedrooms and 1 full bathroom, and one reclining sofa . .Both bedrooms have a queen size beds fully stocked kitchen Our living room has a 55" Smart TV Garage: Parking only on the front of the 1 car garage or roundabout Outside: Our huge yard 2nd floor deck with a patio table and chairs, enjoy the sunrise

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

4.99 out of 5 average rating, 182 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.

Guest favorite

A living area features a large flat-screen television mounted on a light blue wall. A patterned armchair sits to the right, and a round dining table with four chairs occupies the corner, illuminated by natural light from a nearby window.

Apartment in Sycamore

4.93 out of 5 average rating, 30 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

The exterior of the home is highlighted by a well-maintained front yard and concrete steps leading to a white front door. A neatly landscaped area includes low shrubs and decorative stones. A single-car garage is visible to the left, complementing the brick facade.

Home in DeKalb

5 out of 5 average rating, 42 reviews

Duplex in Dekalb, IL

Quiet neighborhood with fenced in yard. Patio and grill with solar lights to keep patio lit. 1 Car garage and driveway available for parking. 2 bedrooms with queen sized beds. Smart TV in one room. Living room has Smart TV as well and cozy sectional to hang out. Kitchen comes with all necessities. Washer and drying available in full unfinished basement. Small dogs (40lbs or less) Please no smoking inside home NIU less than 2 miles away Downtown and shopping area <5miles away

Top guest favorite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

4.99 out of 5 average rating, 163 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favorite

The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.

Apartment in Elgin

4.8 out of 5 average rating, 177 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.