Holiday rentals in Raymond

The State Street Loft | Small Town Charm

Welcome to your spacious 1,700 SF home away from home in the heart of Downtown Litchfield! This 2nd floor loft blends modern updates with old-town charm, featuring 3 comfy bedrooms, 1.5 bathrooms, and soaring ceilings that create an airy, open feel. Enjoy a space with plush seating, high-speed internet, and a workspace - perfect for both relaxation and work. Whether you're here for a weekend escape or an extended stay, this downtown loft is the perfect mix of comfort, style, and convenience.

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

Lake House off Route 66

Lake House Cabin is the best property in the area and offers a 2 acre lot at the end of a peninsula off Route 66. *Includes private lake access with fishing dock. *House has a fenced in dog area with doggie door. *Swimming, paddle boat and fishing allowed* *Crappie, bass bluegill, blue cat and channel cat. *Smoking allowed outside* *Pets 2 max *Crate pets when left alone. *4 person paddle boat *4 Guests Max including kids. *Wifi *No parties*

Historic stay at the 1843 Blackman-Evans Home /4BR

Listed on the National Register of Historic Places, this beautifully preserved 1843 home is steps from downtown Hillsboro. Guests enjoy original architectural details including a locally harvested black walnut staircase, original front door, and stone foundation quarried from Alton, Illinois. Modern comforts include A/C, WiFi, smart TV's and luxury bedding. Experience he charm, history, and comfort of one of Illinois' treasured historic homes.

Relaxing 2 Bedroom House

Relax with the whole family at this peaceful new construction place to stay. Quiet neighborhood close to I-55 and historic Route 66. Beautiful, cozy new furnishings to make your stay very comfortable. Small town quaintness with community park close by with playground, fishing pond, quaint restaurants, and pickleball courts, as well as an area 9 hole public golf course just down the street. This space is a perfect to unwind and relax.

Lakehouse Studio Unit - The Historic Red Rooster Inn

The building has been renovated and two very special overnight accommodations have been created. The location is close to 4th of July Point, Sherwood Forest Campground, Glenn Shoals Lake South Marina, Hillsboro Country Club Golf Course, and is just a few miles from downtown Hillsboro. The tranquil lake setting will prove to be a peaceful retreat from hectic life and a wonderful place to unwind while visiting local family and friends

Harrison House; PETS WELCOME; FENCED YARD

The Harrison House is a beautifully decorated 2-bedroom house that is in a safe neighborhood. WE ARE PET FRIENDLY. The beds are 12” queen memory foam. All the furnishings are new or nearly new. It has a fenced in backyard. KIDS ARE WELCOME. There is a back deck. There is no cable. There is 100 meg wireless internet. There is a ring camera on the porch. You will hear trains. Two tracks run thru middle of town

Downtown Hillsboro Loft

Two bedroom loft space in downtown Hillsboro located above a book and game store and next to a coffee shop and candy store! It’s also walking distance from a brewery, movie theater, live theater, ice cream shop and several local retail stores. The living space displays works of local artisans to complement the hint of mid-century style. With 1200 ft. of living space you will have room for everyone!

The Rustic Modern Loft | Carlinville Square

Experience modern comfort and small-town charm in this beautifully designed apartment on the historic Carlinville Square. Exposed brick, curated decor, and cozy textures create the perfect balance of style and comfort—just steps from local shops, cafés, and restaurants. Designed by Interior Designer Amber Joanna, this space brings a boutique stay experience to the heart of Carlinville.

Timberline Ridge-Tiny Piney

Escape to our cozy tiny log cabin set within a scenic multi-site retreat. Ideal for couples or solo travelers, it blends rustic charm with modern comfort. Relax on your private deck surrounded by nature, with shared space to explore. Enjoy nearby hiking and local shops, then unwind in this peaceful, one-of-a-kind getaway.

Hillsboro Home

Centrally located in Hillsboro, our cozy 3-bedroom, 1-bath Airbnb offers comfort and convenience. Just minutes from downtown, restaurants, shops, laundromat, it's perfect for families or business travelers. Enjoy a fully equipped kitchen, fast Wi-Fi, and a relaxing stay in a quiet neighborhood.