
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.

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.

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

Little Rock Woods Retreat
Escape from it all at our tranquil getaway in the woods. Wander the trails exploring nature on this 26 Acre wooded property, including 1000 ft of frontage along Little Rock Creek. Gather with family & friends for a BBQ on the large screened porch and adjoining deck, play bags or shoot hoops in the spacious yard or just enjoy watching the wildlife and listening to the owls hooting back & forth. With 2 kitchens and 2 laundry areas, smart TVs throughout this is the ideal spot for family gatherings

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.

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.

Adorable 1BR Apt in Sycamore
This adorable unit offers a quiet escape with unbeatable convenience. Just a short distance from downtown Sycamore, downtown Dekalb, NIU, Northwestern Medicine, and other major hubs. You are within minutes from everything. Shopping centers, restaurants, and local stores are within walking distance. Easy convenient parking and quick access to main roads, getting around is very easy. Whether you are here for business, healthcare, or weekend getaway, this well-located space is the perfect stay!

Luxury Meets Cozy
Experience the perfect blend of luxury and comfort at our premier ranch house, designed with sophistication and relaxation in mind. Recently renovated with an eye for detail, this exquisite property is ideal for both festive gatherings and intimate romantic escapes. Nestled amidst lush greenery, the house boasts a sprawling backyard that serves as the ultimate entertainment haven. Every element has been thoughtfully considered to ensure your stay is not only memorable but truly unparalleled.

Pets-Sleeps 7- Event Room Rochelle
Super Clean, Quiet & Cozy! 🐕Pet friendly 🙂Event Room Available -Ask!! (Additional fee ) 90 mi to Chicago! 2 hrs to the Dells! 5 min west of Hwy 39/51 15 min to NIU 45 min to Rockford Walking and bike trail nearby! Beautiful home! Super clean! Monday-Sat check: 3 PM Sunday Check-In: 5 PM Our eight-jet power shower will relax those tired muscles after a full day of activity. A soak in our modern,free-standing tub will sooth and your worries away. A well stocked kitchen awaits you!

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.

2 Townhomes steps from DTWN Geneva Sleeps 14!
Brand-new luxury duplex steps from downtown Geneva, IL! Townhomes are separate units but can be booked together to sleep 14 across 6 beautifully appointed bedrooms with a hotel-style feel. Enjoy 4 full baths + 2 half baths, stunning modern finishes, and spacious living areas. Perfect for large groups, wedding parties, and family getaways. Rent both units side-by-side for the ultimate stay near Geneva’s boutiques, dining, and riverfront charm.

Modern Country Escape | Minutes from NIU
Modern retreat in Malta, IL just 5–10 minutes from NIU & Huskie Stadium! Perfect for parents, alumni, and fans visiting campus, as well as healthcare professionals on local assignments. Enjoy a bright open living area with smart TV, a fully equipped kitchen & coffee bar, cozy bedrooms with fresh linens, fast WiFi, and a quiet neighborhood. Close to downtown DeKalb dining, shopping, and hospitals for both short and long stays.

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 Somonauk St. 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.
Popular amenities for Cortland vacation rentals
Other great vacation rentals in Cortland

Blue Door Cottage, Hot Tub & updated 3 BDR ranch

Cozy home, private location.

Cozy 2 Bed 2 Bath. Walk to downtown Sycamore

The Goat Farm

Family/Pet Friendly Farm House w Firepit Sleeps 10

Paradiso Vacation

Private Heated Indoor Pool + Sauna, Family Retreat

Monarch House in Saint Charles close to downtown
Destinations to explore
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- Six Flags Great America
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Matthiessen State Park
- Wilmot Mountain Ski Resort
- Rosemont Theatre
- Brookfield Zoo
- Allstate Arena
- The 606
- Gurnee Mills
- Lake Geneva Public Library
- Lake Geneva Cruise Line
- Starved Rock State Park Campground
- Wheaton College
- Rivers Casino
- Chicago Premium Outlets
- Fashion Outlets Of Chicago
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Rock Cut State Park
- Cantighy Park
- Buffalo Rock State Park
- Big Foot Beach State Park
- Discovery Center Museum
- Nicholas Conservatory And Gardens





