Vacation rentals in Raymond

More Than a Place to Stay, It’s An Experience!

Welcome to your one-of-a-kind, historic experience located in the countryside just 1 mile east of Springfield city limits. You will experience our finely furnished family home with modern technology & conveniences, originally the one-room North Round Prairie country school from 1875 to 1945. Deluxe features include nature trails, wildflowers, sitting areas, full garage access, and a working cattle farm provide a one-of-a-kind, quality experience. A 3rd bedroom suite upstairs was added in '22!

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.

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.

Audrey's Abode

Audrey’s Abode is just the place you have been looking for to relax and reconnect with family, friends, nature and a simpler time. Located on a 7 acre hobby farm just south of Jacksonville, Illinois (30 minutes west of Springfield), Audrey’s Abode is a fully restored historic log cabin with all the modern amenities for a comfortable getaway. Need additional space? Check out our other listing next door - Bunkhouse Seventy-Four. Pets are welcome but we charge a $35 pet cleaning fee.

The Carlinville Sunset Bungalow

Escape to this charming 3-bedroom, 2-bathroom retreat nestled in the heart of historic Carlinville, Illinois. This beautifully renovated home, with its classic bungalow architecture and cozy interior, is the perfect base for exploring the town's rich history and stunning natural beauty. Perfect for families, groups of friends, bridal parties, or work trips. Inside, you’ll find a fully equipped kitchen, laundry facilities, and all the amenities you need for a memorable stay.

Cozy Home on College Ave

Welcome to our adorable two-bedroom home in the heart of Greenville! Nestled less than half a mile from Greenville University, this cozy retreat offers easy access to 1-70 and Greenville Square. Skip the traditional hotel and enjoy the comfort of a simple home at an affordable rate. With St. Louis just under an hour away, you'll experience the perfect blend of charm, convenience, and proximity to local attractions. Book now for a delightful stay in this inviting space!

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.

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

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!

Edwards House; PETS WELCOME; FENCED YARD

PETS ARE WELCOME. Backyard is fenced. There's a tiled shower, a butcher block bar, king size memory foam bed. Rt 66 is close by. It has 100 meg wireless. There's NO CABLE TV and no local stations. The TV is a smart tv with apps. It is a perfect place to relax or “work from home”. There is digital door access. We'll give you the code, and wont bother you. There is a ring camera on the porch.

Willow's New 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!