Holiday rentals in Sycamore

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Top-rated holiday rentals in Sycamore

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

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Top guest favourite
A bright living area features a cozy sofa and an armchair, arranged around a small desk workspace. Sliding glass doors open to an outdoor patio area, allowing natural light to fill the room. Soft curtains frame the doors, enhancing the inviting atmosphere.
Flat in Elgin
4.99 out of 5 average rating, 95 reviews

Peaceful Elgin APT King Bed

Located in a sleepy suburban neighborhood, this freshly renovated apartment offers everything needed for a weekend getaway, business trip, or extended stay with a full kitchen, open living space, and bedroom. Enjoy peace and nature while still being minutes away from restaurants, shopping, outdoor activities, and all that the Chicago suburbs have to offer. The Tipi BNB is a basement APT that provides guests with the privacy and accessibility of a separate entrance and self check in/check out

Top guest favourite
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, 30 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 favourite
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
4.98 out of 5 average rating, 46 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.

Superhost
A modern living area is presented, featuring a comfortable brown sofa across from a flat-screen television mounted on the wall. A coffee table centers the space, with decorative items and a plant displayed on a side table. Soft curtains frame a window, allowing natural light.
Flat in Sycamore
5 out of 5 average rating, 4 reviews

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!

Top guest favourite
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
4.98 out of 5 average rating, 402 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 favourite
A single-family home features a covered entrance with a red door, framed by several windows. The façade is clad in neutral siding, while a grassy area surrounds the house, partially covered in snow. Leafless trees are visible in the foreground.
Home in Rockford
4.79 out of 5 average rating, 70 reviews

Entire House-Cozy 1-bedroom w/parking (driveway)

This 1-bedroom single family home is in a quiet and safe neighborhood. The home is very cozy and located off of E State Street, the main street in Rockford. Guests can expect a clean house with just about all the amenities that you will need. The living room has two oversized twin pullout beds. This option makes the space ideal for a family vacation. The kitchen is equipped with the essential items needed to prepare meals. The bedroom is equipped with a TV and an ultra comfortable bed.

Top guest favourite
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.
Flat in Aurora
4.98 out of 5 average rating, 197 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 favourite
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.
Flat in Sycamore
4.95 out of 5 average rating, 41 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 favourite
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, 46 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

Superhost
A clear glass table stands against a beige wall, complemented by a modern art piece framed in gold. The artwork features bold colors and abstract designs. A doorway leads to a bathroom area in the background, while light from a stylish chandelier overhead enhances the space.
Guest house in Rockford
4.78 out of 5 average rating, 41 reviews

2 My cozy sweet home

Kick back and relax in this calm, stylish space. Perfect place to relax after work. This is a guest small duplex house semi-attached to the main home. We are located near the Lowes Distribution Center, the Chicago-Rockford International Airport, about 20-minute drive to the Byron Plant, and about 6-to-8-minute drive to downtown Rockford, Discovery Center, Coronado Theatre, BMO Center, and about 12 minutes away from Swedish American Hospital.

Superhost
A modern kitchen features sleek gray cabinetry and stainless steel appliances. A central island with a white countertop is surrounded by black metal stools. Natural light enters through large windows, illuminating a dining area with a wooden table and matching chairs.
Flat in Sycamore
5 out of 5 average rating, 4 reviews

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!

Superhost
A well-appointed kitchen displays teal cabinetry and a contrasting mosaic tile backsplash. Light reflects off the white countertops, while a modern gas stove and a coffee maker are positioned for convenience. A window allows natural light to fill the space.
Home in Sycamore
4.71 out of 5 average rating, 24 reviews

Heart of Sycamore

Nestled in downtown Sycamore, IL, our small charming home blends rustic elegance with modern comfort. Just steps from local shops and Coroco Coffee, and walking distance to Blumen Gardens, it’s the perfect spot to relax and explore. Whether visiting during Pumpkin Fest, enjoying blooming gardens in spring, or exploring year-round, this cozy retreat offers an ideal base for your Sycamore adventures.

Popular amenities for Sycamore holiday rentals

Quick stats about holiday rentals in Sycamore

  • Total holiday rentals

    Explore 20 holiday rentals in Sycamore

  • Nightly prices starting at

    Sycamore holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Sycamore holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sycamore rentals

  • 4.8 Average rating

    Sycamore stays are highly rated by guests – averaging 4.8 out of 5!

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