Holiday rentals in Raymond

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Top-rated holiday rentals in Raymond

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

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Top guest favourite

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

LocationValueDecor

4.98 out of 5 average rating, 83 reviews

Top guest favourite

An inviting interior features a rustic design with wooden accents and a cozy double bed covered in a patterned blanket. A wooden staircase leads to additional sleeping space. A flat-screen TV is mounted on the wall, and details of nature-themed decor can be seen throughout.

Tiny home in Springfield

Tiny Home Cabin - No Cleaning Fee

You won’t forget the peaceful surroundings of this rustic destination. It maybe small at 375 sf, but it has all the features of most hotels with one queen bed and a full bed in the loft. Located near downtown Springfield, IL and many Abraham Lincoln attractions. Deer often walk around the property which is on a quiet dead-end residential street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows. Watch Netflix, Hulu, and Disney also.

LocationFamilyWifi

4.98 out of 5 average rating, 702 reviews

Guest favourite

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.

Flat 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.

ValueLocationAccess

5.0 out of 5 average rating, 42 reviews

Guest favourite

Home in Irving

6-Acre Lake Estate: Boat Dock, Pool, Hot Tub, Pond

Escape to this spacious lakeside estate on 6 private acres! Perfect for groups, the open floor plan flows into an entertainment haven, complete with basement bar and shuffleboard. Outside, your private paradise awaits: dip in the pool, unwind in the hot tub, or fish the pond. Steps away, a private dock offers instant lake access. Nestled in a charming small town, this property blends secluded luxury with local convenience. Parking is a breeze with a spacious garage. Your lake retreat is here!

LocationFamilyAmenities

5.0 out of 5 average rating, 14 reviews

Top guest favourite

The interior of the cabin features exposed wooden beams and reclaimed logs, creating a rustic aesthetic. A comfortable sofa is positioned in front of a brick fireplace, which is flanked by a dresser. A small dining table and chairs occupy one corner, with a cozy area rug enhancing the warmth of the space.

Cabin in Jacksonville

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.

LocationValueIndoor spaces

4.97 out of 5 average rating, 791 reviews

Top guest favourite

A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.

Cabin in Brighton

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.

FamilyValueIndoor spaces

4.98 out of 5 average rating, 124 reviews

Top guest favourite

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.

Guest house 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.

ValueFamilyNearby

4.97 out of 5 average rating, 175 reviews

Guest favourite

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*

LocationFamilyCleanliness

4.88 out of 5 average rating, 113 reviews

Guest favourite

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.

ValueFamilyCheckout

4.89 out of 5 average rating, 66 reviews

Guest favourite

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

ValueLocationIndoor spaces

4.95 out of 5 average rating, 103 reviews

Top guest favourite

A charming two-story home with a light gray exterior and dark shutters is depicted. The front porch features a white railing and steps leading to a blue door. Large windows allow natural light to fill the interior.

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

ValueFamilyLaundry

4.96 out of 5 average rating, 328 reviews

Top guest favourite

Home in Raymond

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!

FamilyValueKitchen

4.98 out of 5 average rating, 51 reviews