Vacation rentals in Raymond

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Top-rated vacation rentals in Raymond

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Top guest favorite
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
4.99 out of 5 average rating, 559 reviews

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.

Top guest favorite
A light-filled living room features a soft blue sectional sofa and a wooden coffee table over a plush area rug. A flat-screen TV is mounted on the wall opposite a decorative fireplace. Natural light enters through sheer curtains, illuminating the space.
Home in Springfield
4.97 out of 5 average rating, 124 reviews

Historic West Side Bungalow

Make some memories at this unique & family-friendly place. You will feel at home in this 3 bedroom/1 bath home. Two main level bedrooms offer king beds, loft offers queen bed & living space. Living room & bedrooms equipped with streaming tv. Xfinity stream & wi-fi is provided. Fully furnished home, well equipped kitchen for many cooking options. You can relax on the rooftop deck or get a little competitive in the LL game room. Onsite laundry. 3 off street parking spots. Conveniently located.

Superhost
A bright sleeping area features a white bedspread over a spacious bed, adorned with mustard-colored pillows and a soft throw. The walls are decorated with framed art and calming phrases. A potted plant adds a touch of greenery, enhancing the cozy environment.
Guest suite in Springfield
4.82 out of 5 average rating, 183 reviews

Modern Central location 1B1B Suite near Downtown

This historic home has the charm of the old house with the new Modern style set up. It is 3 mins drive from downtown Springfield. Within 5 mins drive to the medical district and the historical sites. This basement unit offers a full-sized memory foam mattress with a private bathroom. 55” TV. A dedicated work space, a romantic dining area. It has microwave, coffee machine,toaster and portable stove,front-load Samsung washer & dryer. (Washer & dryer are shared with main floor unit guests!)

Top 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 out of 5 average rating, 25 reviews

Loft Living | Small Town Charm

Welcome to your stylish 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.

Top guest favorite
A cozy dining area is highlighted by a wooden table surrounded by four chairs. Antique stained glass windows illuminate the space with soft colors. A small kitchen area is visible in the background, featuring modern appliances and bright cabinetry.
Cabin in Jacksonville
4.98 out of 5 average rating, 383 reviews

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Top guest favorite
A welcoming living area features a light gray sofa with decorative pillows and a square glass coffee table. A modern accent chair is positioned beside the table, and a shelf displays simple décor. Natural light enters through a large window, creating a bright atmosphere.
Home in Greenville
4.96 out of 5 average rating, 206 reviews

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!

Top guest favorite
A comfortable sleeping area featuring a queen-sized bed with a soft blanket, accompanied by a twin bed upon request. A cozy armchair sits nearby, and natural light filters through large windows, illuminating some indoor plants and decorative elements.
Apartment in Springfield
4.94 out of 5 average rating, 359 reviews

Full studio apartment by the best Springfield park

Historic home attic converted to a private 3rd floor apartment, featuring private kitchen and bathroom. Located just two blocks from what many would agree is the best park in Springfield, with a pond, a botanical garden, tennis courts, a playground, and nice roads to run, walk, bike, or skate on. We are also very close to downtown as well as other commercial areas. This space is on the 3rd floor with private access from outdoor stairs and keypad entry.

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, 130 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.

Top guest favorite
The exterior of the house is presented, showcasing a light gray vinyl siding. A white stairway with railings leads to the front door, which is flanked by simple landscaping. Windows on the façade allow natural light, and a sign indicating the address is visible.
Home in Litchfield
4.94 out of 5 average rating, 392 reviews

Rt 66 House; PETS WELCOME; FENCED YARD

The Rt 66 house is on Historic Rt 66. It is 50 miles North of St. Louis; Right off I-55: PET FRIENDLY; FENCED BACK YARD. There is plenty of room to park a large U-Haul trailer. It is loaded with warm and updated furnishings. It has LOTS of 5* reviews. It has a thick memory foam queen bed. It has a coffee bar. You will hear trains. Two tracks run thru middle of town. 100 meg internet. This is a non smoking house.

Guest favorite
A simple exterior view of the house reveals a white, one-story structure with black accents. The front porch features a small bench and a light fixture beside the door. Lush greenery and freshly mulched beds line the walkway that leads to the entrance.
Home in Raymond
5 out of 5 average rating, 15 reviews

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!

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, 18 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.

Top guest favorite
A serene view of a calm pond reflects vibrant autumn foliage along its banks. Tall trees with orange and yellow leaves surround the water, creating a tranquil natural setting under a clear blue sky.
Cottage in Franklin
4.95 out of 5 average rating, 197 reviews

Peaceful Lake House in the Pines

Take it easy at this unique and tranquil getaway. Perfect spot to relax and get away from it all. The house sits on a beautiful 4 acre lake surrounded by amazing pine trees and 18 acres of meadow full of wildflowers. This property is more than just a place to stay, it is a destination.

Popular amenities for Raymond vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Montgomery County
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