Vacation rentals in Raymond

Newly rebuilt cozy cottage

Small 2 bedroom ensuite family home rebuilt in Craftsman Style in a small town setting. Ample windows providing great source of natural light. Chandelier adorns the living room and a spectacular floral chandelier adorns one bedroom. In the kitchen is a round table providing seating for 4 with additional seat for 2 at the counter top. Gas stove and large refrig. Full laundry provided in basement. Large covered front porch with back patio with round table and umbrella. Grill and firepit in back

Family · Value · View

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.

Value · Location · Accuracy

The Carlinville Cottage

Whether you're in town to visit family, see the sights, or get away for some well-earned time off, this 3-bedroom, 2-bathroom vacation rental is the perfect place to host your next trip to Illinois! This cottage features a modern interior, a well-equipped kitchen, and a large backyard with plenty of space for kids and pets to run around. Spend your days exploring the nearby historic district of Carlinville and enjoying the surrounding attractions before heading home for a relaxing night in.

Location · Family · TV

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.

Location · Value · Air conditioning

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.

Location · Family · Checkout

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*

Value · Location · Bathroom

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.

Value · Location · Indoor spaces

Lakehouse Two Bedroom 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

Family · Value · Check-in

The Campground House

Escape to a private retreat just an hour from St. Louis! Our charming getaway offers a peaceful, country atmosphere where you can relax and unwind or dive into nature. Need more space or a unique experience? Check out our sister property, Timberline Ridge - Tiny Piney! Perfect for additional accommodations or a unique change of scenery, Tiny Piney offers cozy and rustic charm that complements your stay at The Campground House.

Family · Location · Check-in

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

Value · Family · Comfort

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!

Location · Value · Bathroom

Willow's New 2 Bedroom House

Kick back and relax in this calm, stylish space. Located in a quaint, quiet community within walking distance to a golf course and ice cream. This new construction is easy to get to and not far from Historic Route 66 or I-55. Whether you're visiting family, or on your way through, Willow's house will feel just like your home!

Family · Location · Laundry