Vacation rentals in Raymond

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Top-rated vacation rentals in Raymond

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

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Guest favorite

The spacious living area features a combination of modern and rustic elements, with three windows allowing natural light to illuminate the space. Plush seating includes two recliners and a small table, complemented by a stylish desk for work. Exposed brick walls add character to the setting.

Apartment in Litchfield

5.0 out of 5 average rating, 38 reviews

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.

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Top guest favorite

A small, modern building is presented with blue siding and a stone foundation. A wooden pathway leads to a white front door, bordered by simple landscaping with gravel. Lush greenery is visible on both sides, enhancing the sense of privacy.

Guesthouse in Carlinville

4.98 out of 5 average rating, 159 reviews

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.

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Guest favorite

A collage of four images showcases the property’s inviting features. The theater room displays plush seating, while the cozy bedroom highlights soft textures and warm colors. The outdoor area reveals a spacious seating arrangement surrounding a fire pit, and the living room is arranged with a comfortable sectional.

Home in Springfield

4.92 out of 5 average rating, 199 reviews

Abe's Hideaway - HOT TUB, Arcade, Theatre, FUN!

Our property is not just a place to stay; it's an experience in itself! Enjoy our hot tub, arcade, & theater room, PLUS unique "hideaways" that let kids (& kids at heart) play hide & seek in a whole new way. Nestled in a tranquil subdivision near Lake Springfield, our spacious haven offers a gateway to the city's vibrant attractions and beyond. With convenient access to I-72 and I-55, you're just moments away from all that Springfield has to offer.

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Guest favorite

Home in Mount Olive

4.87 out of 5 average rating, 105 reviews

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*

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Guest favorite

A compact kitchenette is featured, showcasing black appliances including a refrigerator and stovetop oven. A sink with a modern faucet is set against a wooden countertop. Storage cabinets are present, and a clock is mounted on the wall. Natural light illuminates the space.

Apartment in Hillsboro

4.94 out of 5 average rating, 102 reviews

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

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Top guest favorite

A single-story house features a light-colored exterior with a gray roof. Large windows allow natural light to enter. Shadows cast by nearby trees create a peaceful setting, while a gravel driveway leads to an open outdoor space with seating and rustic decor.

Home in Carlinville

4.97 out of 5 average rating, 122 reviews

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.

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Top guest favorite

A living area features a brown leather sofa and recliner, arranged around a wooden coffee table. A patterned area rug adds texture beneath the furniture. A colorful cow painting is displayed on the wall, while natural light filters through a nearby window.

Home in Litchfield

4.96 out of 5 average rating, 320 reviews

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

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Guest favorite

The Victorian house displays a charming exterior with light blue siding and a distinctive turret. Lush greenery frames the entrance, which features a welcoming front porch and decorative stonework. The large windows allow natural light to enhance the inviting façade.

Home in Carlinville

4.99 out of 5 average rating, 76 reviews

Victorian Home on Rt. 66

Genteel architecture and classic Victorian woodwork define this unique house’s attraction. Inside you’ll find the comfort and hospitality of a bygone era of class and elegance. Located on historic Rt. 66 near the restaurants and shops of Carlinville's charming square. There is a TV in the living room and smart TVs in the bedrooms. Level 2 EV charger. Bring your own NEMA 14-50 compatible cable.and elega

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Top guest favorite

A comfortable sofa is positioned in front of a vibrant accent wall featuring orange and blue geometric patterns. Natural light filters through a nearby window, illuminating the space, which is complemented by light wood flooring and neutral-colored walls.

Loft in Hillsboro

4.94 out of 5 average rating, 117 reviews

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!

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Guest favorite

The exterior of the historical home features a charming brick facade with a welcoming front porch. Colorful flowers are arranged along the walkway, and steps lead to the entrance. Large windows allow natural light to brighten the space, creating an inviting atmosphere.

Home in Hillsboro

4.91 out of 5 average rating, 53 reviews

Whitledge-Canaday House

This historical house is perfect for those who are deemed history buffs. This location brings back the old memories of the Canaday family while highlighting the little town of Hillsboro. This house embraces its past while incorporating a modern twist. Perfect for guests that are passing through, visiting family around the area, or those who simply want to relax.

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Top guest favorite

Home in Raymond

4.98 out of 5 average rating, 42 reviews

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!

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Guest favorite

A single-story house is shown with a light-colored exterior. Steps lead to a covered porch, where a light fixture is visible beside the door. A gravel driveway and patches of green grass are present, surrounded by trees and a peaceful landscape.

Home in Hillsboro

4.94 out of 5 average rating, 36 reviews

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.

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