Vacation rentals in Raymond

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Top-rated vacation rentals in Raymond

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Top guest favorite

The craftsman-style home is framed by lush green grass and flower beds. A welcoming front porch is adorned with white railings and seating, providing a comfortable entryway. Steps lead up to the front door, under a blue sky dotted with clouds.

Home in Taylorville

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

4.98 out of 5 average rating, 82 reviews

Top guest favorite

The living room features a comfortable sofa paired with two patterned armchairs, creating a cozy seating area. A light-toned rug anchors the space, while a small coffee table sits centrally. A dining area is visible in the background, illuminated by natural light.

Home in Auburn

The Cottage at Edgewood

Located along the sixth fairway of Edgewood Golf Club and 20 minutes south of Springfield, our State Capital, the Cottage at Edgewood is a newly renovated ranch style, single-family home. Whether you’re visiting family, playing golf, touring the Land of Lincoln sites, or cruising Route 66, the Cottage is convenient for all. Guests have exclusive use of the entire house, with a large yard and walkout patio perfect for enjoying your morning coffee, evening drinks, and waving to golfers passing by.

5.0 out of 5 average rating, 52 reviews

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

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.

5.0 out of 5 average rating, 39 reviews

Guest favorite

A bright living area features a plush sofa adorned with patterned cushions, complemented by a round coffee table. Artwork is displayed on the walls, and a stylish ceiling fan hangs overhead. Natural light filters through multiple windows, enhancing the open space.

Home in Carlinville

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.

4.96 out of 5 average rating, 54 reviews

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

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. All bedrooms are located on the second floor. 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

4.99 out of 5 average rating, 77 reviews

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

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.

4.98 out of 5 average rating, 166 reviews

Guest favorite

Home in Mount Olive

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*

4.87 out of 5 average rating, 110 reviews

Guest favorite

The cottage showcases a Southern-style design with a welcoming front porch framed by green shutters on large windows. Lush greenery lines the property, complementing the natural surroundings. The gabled roof adds to the home’s historical charm.

Home in Hillsboro

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.

4.89 out of 5 average rating, 62 reviews

Guest favorite

A dining area features a wooden table set for six, accompanied by metal chairs. Colorful bowls are placed on the table, complementing a decorative centerpiece. A sign with the word 'hello' adorns the wall above, and a floor lamp adds gentle illumination to the space.

Home in Hillsboro

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

4.95 out of 5 average rating, 102 reviews

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

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.

4.97 out of 5 average rating, 122 reviews

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

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

4.96 out of 5 average rating, 322 reviews

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

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!

4.94 out of 5 average rating, 119 reviews