Holiday houses in Sycamore

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.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

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.

Event Room & Pool available, Pets Free

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!

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.

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.

Delightful 1BR Apt in Sycamore

Delightful 1 Bedroom unit- Enjoy a peaceful retreat in this charming, well-located apartment just minutes from downtown Sycamore, DeKalb, Northern Illinois University, and Northwestern Medicine. Perfect for business travelers, medical visits, or weekend getaways. Walk to local shops, shopping centers, restaurants, and grocery stores. Easy, free parking and quick access to major roads make exploring effortless. Stylish, comfortable, and convenient—your ideal home away from home awaits.

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.

124 Lofts #2 - 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 #2, 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.

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.

Spacious 3 bed 2 bath with King Master in Sycamore

This condo is conveniently located in the quaint, quiet town of Sycamore! The home offers 3 bedrooms, 2 full baths, full kitchen, washer/dryer, basement, 2 car attached garage, and a gas fireplace. The home has 2 smart TV's and Wi-Fi is included. The home is located just minutes from all major shopping, the quaint downtown main street of Sycamore, NIU, and interstate 88! Perfect for short stays in the city!