Vacation rentals in Fillmore

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Top-rated vacation rentals in Fillmore

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Top guest favorite

A well-lit outdoor space is presented, featuring a wooden walkway leading to a cozy fire pit surrounded by natural landscaping. Soft string lights create a warm ambiance, enhancing the serene atmosphere of the wooded area, perfect for evening gatherings.

Apartment in Edwardsville

4.92 out of 5 average rating, 357 reviews

Edwardsville Apartment - The Woodland Suite

The apartment in the lower level of the home has recently been renovated, with a walk-out private entrance, a full kitchen & dining area, full bath, bedroom and a cozy living space. Situated just 35 minutes from downtown St Louis, in the safe and affluent community of Edwardsville, this property sits in a quiet cul de sac on a wooded lot right in the heart of the city. We are just a few minutes from the SIUE campus, Edwardsville HS, & I-270. Coffee/restaurants/shops/parks/trails just 2 min away.

Guest favorite

A cozy sleeping area features a spacious bed with multiple pillows in neutral tones. Wall sconces provide gentle lighting on either side. A decorative sign with the word 'welcome' is displayed above the headboard, adding a personal touch to the inviting space.

Apartment in Teutopolis

4.95 out of 5 average rating, 596 reviews

The Shoe Inn, a modern apt in downtown Teutopolis

Welcome to The Shoe Inn! You'll be at the center of town within walking distance to all the places you need to be: banquet halls, five bars, restaurants, Wessel's grocery store, ice cream shop, church, hardware store, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer (no detergent provided) , fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free WiFi

Top guest favorite

The living area features a dark leather sofa accented with patterned cushions, paired with a wooden coffee table. A breakfast bar with two stools separates the space from a modern kitchen, equipped with white cabinetry and ample counter space. Window blinds provide natural light.

Home in Litchfield

4.98 out of 5 average rating, 125 reviews

Edwards House; PETS WELCOME; FENCED YARD

Find all of our Litchfield homes by searching "softstays" on the internet. PETS ARE WELCOME. Back yard 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. 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. You will hear trains. Two tracks run thru middle of town.

Top guest favorite

A rural building is shown, featuring a red and gray exterior with two prominent roof peaks. Nearby, a gravel pathway leads to the entrance, surrounded by grassy areas and trees. Soft evening light enhances the peaceful setting, highlighting the natural surroundings.

Barn in Bingham

4.98 out of 5 average rating, 61 reviews

Down on the Farm

Remote area that's about 15 min from Interstate 70. Quiet & peaceful w/minimal road traffic. Farming area. In warm weather, fish in our pond or visit/fish nearby Ramsey Lake State Park. Amish in the area & a local Amish market. Go for walks in our wooded area. Relax on a private deck in the evening. Queen bed, full bed, as well as a couch w/matching loveseat. NOTE on pets: 1 small pet under 25 lbs. allowed: PLEASE read our pet rules & agree to follow them before requesting a reservation.

Guest favorite

An outdoor patio area features a large umbrella providing shade over a seating arrangement with several chairs and a table. A charcoal grill is positioned nearby, along with a small trash bin. Lush greenery from the surrounding woods serves as a backdrop.

Home in Fillmore

4.93 out of 5 average rating, 59 reviews

The Rabbit’s Den w/ Private Entrance - 4BR

This bi-level ranch style home fully immerses you into nature while sitting on 30 acres of scenic farmland. Guests would have a the entire lower level of the home with private entrance. The fully furnished lower level is equipped with a full kitchen, four TV’s for streaming, living room, laundry room, full bathroom, and 4 separate bedrooms. Private patio with charcoal grill and fire pit face the woods. Parking near entrance. Handicapped accessible. Shower chair. No work groups.

Top guest favorite

A spacious lawn leads to a serene three-bedroom home, surrounded by trees and greenery. The property features a view of a pond in the distance, with the American flag gently waving near the entrance.

Cottage in Brownstown

4.99 out of 5 average rating, 172 reviews

Shagbark Landing

Forget your worries in this spacious and serene space. Drive down the lane to a secluded 3 bedroom home newly furnished. Enjoy yourself in an open concept floor plan where there is lots of room to spread out. Spend your evenings in the living room or the family room that has a fireplace. From the family room you can step out on a deck and enjoy the view of the pond. We are located 8.5 miles from Vandalia where there are historical landmarks, great restaurants, and quaint shops.

Top guest favorite

The bedroom features a queen-sized bed, complemented by exposed brick walls and two windows allowing natural light to fill the space. Soft drapes frame the windows, while nightstands with lamps provide gentle illumination, creating a calm and inviting atmosphere.

Loft in Vandalia

4.94 out of 5 average rating, 284 reviews

Modern Loft in Historic Downtown

Lincoln’s Loft is close to everything making it easy to plan your visit to downtown Vandalia. This loft offers a bedroom, full kitchen and bath, dining room, living room with a pull out sofa, and large smart TV. This loft also offers beautiful views of the oldest State Capitol in IL and is within walking distance to many restaurants, bars, and local shops. It is located on the 3rd level and will require you to climb 2 flight of stairs. For events please contact the host!

Top guest favorite

An open interior showcases a spiral staircase leading to a loft area. A wooden table with seating for four is located in the foreground, complemented by a small kitchen featuring appliances and exposed brick. Natural light enters through the windows, enhancing the warm tones of the space.

Home in Teutopolis

4.96 out of 5 average rating, 229 reviews

Wooden Shoe Factory, Historic, w/ Bar & Breakfast

Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

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

4.95 out of 5 average rating, 172 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 cozy cottage is positioned within a spacious yard, surrounded by greenery and a fence. A clear blue sky and open fields are visible in the background, highlighting the rural setting. Nearby features include a small shed and animal enclosures.

Guesthouse in Effingham

4.93 out of 5 average rating, 410 reviews

Country cottage tiny home.

This 240sq ft cottage offers big living in a tiny space. The cottage is on our 2 acre property that is used for a hobby farm and primary residence. The cottage features luxury vinyl flooring, granite counter tops and an updated farm house feel. The queen size bed is sure to provide the right amount of comfort. When you wake up, walk on over and grab a cup of coffee from the keurig. Enjoy a walk around to see the goats and chickens before heading off for the day.

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, 100 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

A single-story home is set on a well-maintained lawn, featuring a paved driveway leading to an attached garage. The exterior showcases a mix of light-colored siding and stone accents, framed by mature trees and shrubs, with large windows allowing natural light into the interior.

Home in Vandalia

5 out of 5 average rating, 151 reviews

Modern family friendly home in Historic Vandalia

Beautiful completely updated home with all new items. 2 blocks from the park and swimming pool, stroller in garage if needed. Across the road from the hospital, 2 blocks from public schools, 1 mile from walmart, close to many restaurants and coffee shop. Deck with outdoor seating and fenced in back yard and a corn hole game perfect for this beautiful back yard. And a charcoal grill ready to use.