Vacation rentals in Saybrook

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Top-rated vacation rentals in Saybrook

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

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Top guest favorite
Cabin in Heyworth
4.97 out of 5 average rating, 229 reviews

Sauna & Hot Tub A-Frame | 2-Acre Wooded Retreat

Hidden Grove: Private 2-acre wooded retreat near Bloomington, IL featuring a new outdoor sauna, hot tub under the stars, fire pit for s'mores, hammock, and Corn-hole. Steam away the stress, soak beneath a canopy of trees, and let the quiet woods slow your pace. Just a few minutes from hiking trails, outdoor adventures, and local restaurants, yet miles away from your stress. A serene luxury escape perfect for couples, families, or friends craving a true nature reset. Rejuvenate, relax, reconnect.

Top guest favorite
A historic two-story home features a large front porch with white railings, surrounded by a well-maintained lawn and decorative flower planters. Tall trees provide shade, and a driveway leads to a two-car garage at the side.
Loft in Monticello
4.99 out of 5 average rating, 818 reviews

Monticello Carriage House

This carriage house is located at the back of the property of a 117-year-old historic home 4 blocks from downtown shopping and dining. We're 15 minutes from Allerton Park & Retreat Center, 25 minutes to Champaign and 30 minutes from Decatur. You’ll enjoy the comfy bed, two dining/game spaces, TV area, a small kitchen with cooktop, small refrigerator, microwave, coffee pot and a full bathroom. It is great for a weekend get-away! Come to enjoy Monticello! Same-day bookings-6:30 check-in time

Top guest favorite
Home in Hudson
4.98 out of 5 average rating, 154 reviews

Timber Time in Hudson Hideaway

Looking for a break from the busyness of life, to relax and enjoy nature? Step back in time in this tranquil and rustic home. In a remote location and surrounded by timber, this property is perfect to unwind, enjoy a sunset, and view the stars in a wide-open sky. The large yard allows for all kinds of activities and the circle drive provides easy RV, trailer, and boat access. Located next to Evergreen Lake/Comlara Park, the hiking and biking trails, boat ramp, and beach are just minutes away.

Top guest favorite
A living area features a comfortable brown sofa and a blue armchair, complemented by a light-colored coffee table. Natural light enters through sliding doors, revealing a glimpse of the outdoor surroundings. A map decorates the wall, adding a hint of history to the space.
Home in Rantoul
4.98 out of 5 average rating, 165 reviews

No Fees! - The Chanute - Your Home Base

Located in Rantoul, Illinois, this two bedroom, one bath gem has been lovingly transformed to celebrate the history of Chanute Air Force Base and honor the base's namesake, Octave Chanute. Situated in a quiet neighborhood, THE CHANUTE provides guests with easy access to local highlights such as the Rantoul Sports Complex, B52 BMX track, Gordyville USA, & Flyover Studios, while only requiring a short drive to visit the University of Illinois and other attractions throughout Central Illinois.

Top guest favorite
A serene bedroom is highlighted by a large tufted bed with decorative pillows and a warm throw. Natural light filters through elegant curtains at the windows. A stylish chandelier and a decorative mirror above a contemporary dresser enhance the chic ambiance, complemented by soft wall colors and textured accents.
Apartment in Fairbury
5 out of 5 average rating, 438 reviews

Chic Retreat Small Town Charm, City Sophistication

The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book a week long stay and receive 40% off ❤️

Top guest favorite
A renovated red caboose, TP&W 527, is positioned on railroad tracks surrounded by grass. The structure features white wheels and an elevated cupola, with windows and a yellow emblem. Green trees provide a natural backdrop, and a cobblestone pathway leads to the entrance.
Train in Oreana
4.99 out of 5 average rating, 162 reviews

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Guest favorite
A bright living area features two comfortable sofas and a stylish armchair arranged around a coffee table. Natural light enters through windows covered with light drapes, complementing the neutral color palette and wooden floor. A decorative plant and artwork add subtle elements of warmth.
Home in Rantoul
4.91 out of 5 average rating, 121 reviews

Tiny Home, Clean, Baby-Friendly

Welcome to your perfect home-away-from-home! We are delighted to present a stunning and newly remodeled, baby-friendly short-term furnished rental, located just steps away from an historic air force base and across from a picturesque lake. With a comfortable size of 625 sq ft, this inviting space is ideal for those seeking convenience, tranquility, and modern amenities. HUGE backyard, fully fenced, for your relaxation and enjoyment. Perfect for professionals, families, or vacationers.

Top guest favorite
The open-concept living area features a sleek black sofa and a decorative area rug. A staircase leads to the loft space above. Large windows allow for natural light, while wooden accents on the walls and ceiling create a warm, inviting environment.
Home in Potomac
4.94 out of 5 average rating, 251 reviews

Wren House in the Woods

This is a lovely private guest house in the woods along a stream Main bedroom has queen bed. Loft has 2 twins. Full private bath with large step in shower. The lighted screened porch and open deck sit above the west creek near the banks of the Middlefork River -- enjoy nature at its midwestern best. This home is surrounded by oaks, maples, and walnut trees, so the birds are all around, along with other wildlife. Think night sounds of wildlife and birds early in the morning and no TV

Guest favorite
A bright living area features two red accent chairs and a light round table set against large windows draped with dark curtains. A spacious gray sectional sofa and a wooden coffee table provide comfortable seating, while unique ceiling tiles add character to the room.
Vacation home in Paxton
4.99 out of 5 average rating, 154 reviews

Arnie’s Place, A big little space in a small town!

Take it easy at this unique and tranquil getaway. Located above a little fun popcorn shop, this place is newly renovated! Located in the heart of downtown Paxton, IL it puts you close to shopping and restaurants and 10 minutes from the Rantoul sports complex and 30 minutes from the University of Illinois Campus. Arnie’s Place is a perfect place for a couples get away, girls trip, small gatherings, a few nights stay for sporting events, a quiet place to relax and unwind.

Top guest favorite
The spacious living area features exposed brick walls and hardwood flooring. A television is positioned near a comfortable seating arrangement, while a large dining table accommodates multiple guests. Natural light filters through tall windows, and a striking piece of artwork hangs on the wall.
Loft in El Paso
4.94 out of 5 average rating, 622 reviews

The Courthouse Loft-History, hot tub, and coffee!

The Courthouse Loft resides in the historic courthouse used in the mid 1900s on the second floor of The City House. The original railing and gate of courtroom divides the 825 soft studio style layout. Loft has a separated bath and laundry and a patio with hot tub! Mid century and historic style will wrap you in comfort and luxury during your stay. We are above a coffee shop, so pop downstairs for breakfast and your morning brew! Oh, and never a cleaning fee!

Top guest favorite
The living room features a spacious sectional sofa in neutral tones, accompanied by a wooden coffee table. Natural light enters through the large windows, with light curtains framing the view. A ceiling fan is present, enhancing air circulation. Decorative art is displayed on the walls.
Home in Clinton
4.97 out of 5 average rating, 142 reviews

Upper Deck

Beautiful 3 bedroom home. Conveniently located on the edge of town, minutes from Clinton Lake and Historical downtown Clinton. Close to multiple restaurants, shopping and other entertainment options. The home has a well stocked kitchen with a charming dining room. There is also a large back deck with furniture and a grill. Plenty of on-premise parking. This is a second story home so there are stairs to access the property.

Top guest favorite
A driveway leads to a garage with two doors, bordered by manicured grass. A swing hangs from a tree nearby, with open fields visible in the background under a partly cloudy sky.
Home in Roanoke
4.97 out of 5 average rating, 116 reviews

Sage Inn

Charming property conveniently situated between Peoria and Bloomington, IL metro areas. A stone's throw to Roanoke Park and Pool (open seasonally from Memorial Day to Labor Day) including a renowned disc golf course. Amenities include: access to WiFi, full kitchen, Smart TV, Washer/Dryer, Electric Fireplace, Futon in the living room folds out into a queen bed for additional sleeping arrangements.

Popular amenities for Saybrook vacation rentals