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Vacation rentals in Sycamore

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Quick stats about vacation rentals in Sycamore

  • Total vacation rentals

    Explore 10 vacation rentals in Sycamore

  • Nightly prices starting at

    Sycamore vacation rentals start at R 809 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 570 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Sycamore vacation rentals include wi-fi 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!

Top-rated vacation rentals in Sycamore

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

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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.
Barn in Clare
4.93 out of 5 average rating, 112 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.

FamilyValueHeating

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
4.92 out of 5 average rating, 181 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

ValueLocationHospitality

Top guest favorite
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.
Apartment in Elgin
4.99 out of 5 average rating, 113 reviews

Peaceful Elgin APT King Bed

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

ValueLocationHospitality

Guest favorite
A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg
4.94 out of 5 average rating, 887 reviews

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!

ValueLocationCleanliness

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
4.98 out of 5 average rating, 65 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.

LocationValueSleep quality

Guest favorite
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.
Apartment in Sycamore
4.93 out of 5 average rating, 14 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!

LocationViewLayout

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
4.98 out of 5 average rating, 53 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.

FamilyLocationHospitality

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.
Apartment in Cherry Valley
4.97 out of 5 average rating, 469 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.

FamilyLocationEV charging

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, 278 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.

LocationValueKitchen

Top guest favorite
Loft in West Dundee
4.96 out of 5 average rating, 424 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.

LocationValueRiver

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
4.94 out of 5 average rating, 133 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!

LocationFamilyHeating

Top guest favorite
Apartment in Sycamore
4.97 out of 5 average rating, 88 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. 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.

LocationValueHospitality

Popular amenities for Sycamore vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Sycamore

Guest favorite
The exterior of the home showcases red shingle siding and features a combination of larger and smaller windows. A concrete pathway leads from the sidewalk to the front steps, which ascend to the entrance. A tree and grassy area are visible in the foreground.
Home in Sycamore
4.88 out of 5 average rating, 8 reviews

Cozy 2 Bed 2 Bath. Walk to downtown Sycamore

FamilyLocationAccuracy

Top guest favorite
A spacious living area features modern furniture, including a plush blue sofa and two accent chairs. Unique pendant lights provide ambient illumination, while an open kitchen with a sleek design offers an inviting atmosphere. Large windows allow natural light to fill the space.
Home in St. Charles
4.98 out of 5 average rating, 58 reviews

Luxury Meets Cozy

FamilyValueBackyard

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
5.0 out of 5 average rating, 55 reviews

Duplex in Dekalb, IL

FamilyLocationAccuracy

Superhost
Home in Malta
4.78 out of 5 average rating, 23 reviews

Modern Country Escape | Minutes from NIU

FamilyValueIndoor spaces

Guest favorite
Guesthouse in Steward
5.0 out of 5 average rating, 11 reviews

"The Coop" on the Farm ! Peaceful & Cozy

FamilyLocationPool

Top guest favorite
A stone-clad cottage is set against a clear blue sky, featuring a stylish balcony and vibrant green trees. A winding path leads to the entrance, flanked by neatly trimmed shrubs and a gravel border, inviting guests to explore the charming surroundings.
Farm stay in Marengo
5.0 out of 5 average rating, 14 reviews

Villetta Bogdano

LocationFamilyNearby

A well-lit living area is observed with two armchairs positioned near a round coffee table. A large television is mounted on the wall across from the seating. Natural light filters through the windows, accentuating the warm wood floors and neutral walls.
Apartment in Sycamore
4.67 out of 5 average rating, 111 reviews

Stylish BoHo Mid-Century Aptmnt -Downtown Sycamore

FamilyLocationOutdoor spaces

A spacious living area is highlighted by a comfortable sofa with colorful pillows and a sleek armchair. Warm light from a nearby lamp illuminates a wooden desk, while large windows feature blinds providing natural light control.
Apartment in DeKalb
4.6 out of 5 average rating, 53 reviews

The Rustic House

LocationFamilyNearby

Frequently Asked Questions

  • What are the best places to stay in Sycamore?

    Many visitors enjoy staying near Sycamore’s historic downtown area for easy access to shops, dining, and community events. Rentals in quiet neighborhoods often provide outdoor space and a relaxed home base.

  • What are the best things to do in Sycamore with kids?

    Families can explore local parks with playgrounds, visit hands-on exhibits at the Sycamore History Museum, or look for seasonal community events that welcome children. Many local bakeries and ice cream shops are frequently suggested for a sweet stop.

  • What are some of the best things to do in Sycamore?

    You can explore historic downtown Sycamore with its shops and cafes, visit local museums, or spend time in nearby parks with walking trails. Community events and markets add to the small-town character throughout the year.

  • How is the weather in Sycamore?

    Sycamore experiences cold winters around 13–33°F (-10–1°C), with moderate snowfall, and warm summers near 80–82°F (26–28°C). Spring and autumn bring mild days and cool nights, so layers are helpful for changing conditions.

  • When is the best time to visit Sycamore?

    Early fall is often recommended due to seasonal festivals and comfortable temperatures. Spring and summer are also pleasant, with mild weather and outdoor events, while winter provides a quieter atmosphere.

  • What are the best places to visit in Sycamore?

    Sycamore has a historic Main Street area with shops and local dining, the DeKalb County History Center, and parks where people often gather for picnics. Seasonal markets and community events add to the lively atmosphere around the town center.

  • What are some hiking trails in Sycamore?

    Sycamore has local parks with walking and biking trails suitable for all ages. Nature enthusiasts often explore forested paths, prairie areas, and paved routes in and around the community.

  • What are some family activities we can do in Sycamore?

    Families can spend time together at playgrounds, picnic areas, and seasonal farmers markets. Exploring the Sycamore History Museum and taking part in local festivals also provide engaging, family-oriented experiences.

  • What are some of the best day trip ideas from Sycamore?

    Around Sycamore, you can explore nearby nature preserves, visit orchard farms in the region during harvest season, or discover local art galleries in surrounding towns. Regional history museums and forested parks are frequently suggested for short excursions.

  • Are there any pet friendly accommodations available in Sycamore?

    Some accommodations in Sycamore are pet friendly, often providing easy access to local parks and trails for daily walks. Check with your host about specific pet policies to ensure a comfortable stay for everyone.

  • What are some local tips for visiting Sycamore?

    Exploring on foot allows you to discover local shops and historic architecture in downtown Sycamore. Early fall is often recommended for visiting local festivals, and packing comfortable shoes can help with enjoying local parks and trails.

  • What is Sycamore known for?

    Sycamore is known for its historic downtown with preserved architecture, an annual fall Pumpkin Festival, and a friendly small-town atmosphere. Its local parks, community events, and agricultural heritage shape the area’s character.

  • What are the best hidden gems to explore in Sycamore?

    Discover Sycamore’s tucked-away antique shops, small local art galleries, and quiet neighborhood parks. Walking historic residential streets reveals unique architecture and pocket gardens not always found in guides.

  • What are the best foods to try in Sycamore?

    Sycamore is known for classic Midwest comfort fare, including hearty sandwiches, locally made pizza, and seasonal baked goods. Visitors often seek out farm-fresh produce, homestyle breakfasts, and homemade pies at local diners or bakeries.

  • What should I bring for a trip to Sycamore?

    Pack weather-appropriate layers, as temperatures shift by season, along with comfortable shoes for exploring downtown and parks. In cooler months, a warm jacket, gloves, and hat are useful, while spring and summer visitors may want rain gear and sun protection.

  • What is the nightlife in Sycamore like?

    Sycamore has a relaxed nightlife scene with casual bars, local pubs, and some live music venues. Many visitors enjoy neighborhood restaurants that feature regional brews, seasonal cocktails, and comfort food.

  • What are the most popular events or festivals in Sycamore?

    Sycamore is known for its annual fall Pumpkin Festival, which draws visitors for themed parades, arts, and local foods. Seasonal farmers markets and summer concerts in the park are also popular community gatherings.

  • Are there family friendly vacation rentals in Sycamore?

    Sycamore has a variety of vacation rentals suitable for families, including homes with roomy living spaces and outdoor areas. Many are situated near parks and quiet residential neighborhoods, making them a convenient base for family activities.

Destinations to explore