Vacation rentals in Fillmore

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Top-rated vacation rentals in Fillmore

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Guest favorite

A couple stands on a stone path leading through a green landscape, with a flowing creek visible in the background. The sun shines brightly, enhancing the natural beauty of the outdoor setting, surrounded by trees and open fields.

Home in Fillmore

4.94 out of 5 average rating, 69 reviews

Pheasant Valley Farms

Enjoy your stay in your very own farmhouse. Nestled in rolling hills, with views of the flowing creek and fields. Just 6 miles East of Hillsboro, IL & 45 minutes from Springfield, IL Enjoy hiking, fishing, golf, boating and relaxing on the porch. The farmhouse has 1 bedroom with a queen bed and comfortable sofa sleeper (double) in the living room. There is also a bed/futon in the summer kitchen (separate structure, no bathroom). Best used in cooler weather, no A/C. It is more of a man cave

Superhost

A designated fire pit area is surrounded by four comfortable chairs, set within a gravel space amid lush greenery. A small grill is visible in the background, adding to the outdoor ambiance. Smoke gently rises from the fire, creating a serene atmosphere.

Tiny home in Mulberry Grove

4.87 out of 5 average rating, 92 reviews

*Tiny Home In The Woods*Firepit*Cozy*Pets Welcome

Need a break? Some time to relax and breathe? Come get away from it all at this TINY HOUSE in the woods. Roast s'mores around the fire pit, go kayaking on nearby Carlyle Lake, stargaze on the porch swing with a cozy blanket...or just cuddle up and binge watch your favorite shows in bed or in front of the fireplace. Fully updated with everything you need: full size washer/dryer, stocked kitchen, smart TVs, wifi, outdoor grill, 2 RV hookups, space to park a boat - conveniently right off of I-70!

Guest favorite

A modern seating area features a round wooden table and two black chairs. A wall-mounted TV displays a serene image, while an electric fireplace below adds warmth to the space. A circular mirror reflects light from the cozy interior.

Apartment in Teutopolis

4.95 out of 5 average rating, 571 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

A peaceful scene depicts a rustic cabin surrounded by tall trees, set beside a calm pond. The dusk sky casts a soft glow on the space, with an outdoor picnic table positioned on a stone patio. Warm lights illuminate the cabin, enhancing the tranquil environment.

Barn in Bingham

4.98 out of 5 average rating, 53 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 pavilion provides a shaded gathering space, illuminated by soft golden lights. Equipped with seating, a grill, and a refrigerator, the structure is surrounded by a spacious lawn and mature trees, creating a serene atmosphere for gatherings.

Home in Fillmore

4.92 out of 5 average rating, 49 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 deck offers views of a serene pond, surrounded by lush trees. Outdoor furniture, including a round table and comfortable seating, creates an inviting area for relaxation. A patterned area rug adds a decorative touch to the wooden deck.

Cottage in Brownstown

4.99 out of 5 average rating, 160 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.

Guest favorite

A light-filled area features a classic electric piano set on a small stand, positioned against a wall. The smooth flooring is complemented by neutral-colored walls. A sideboard with decorative items is visible in the background, enhancing the welcoming ambiance of the home.

Home in Litchfield

4.96 out of 5 average rating, 134 reviews

Jackson House; PETS WELCOME

Find all of our Litchfield homes by searching "softstays" on the internet. The Jackson House is a spacious 2-bedroom home located in a safe, quiet neighborhood. PETS ARE WELCOME. It has 2 bedrooms with king-size memory foam beds. There is a washer/dryer on the main level. This home has various musical instruments for the music fan. NO cable TV. 600 meg wireless internet. There is a ring camera on the porch. You will hear trains. Two tracks run thru middle of town.

Top guest favorite

A compact bathroom is featured, showcasing a white shower curtain and a spacious sink area. A small shelving unit displays various green and blue jars. The flooring highlights warm tones, complemented by a textured bath mat in front of the toilet.

Home in Greenville

4.95 out of 5 average rating, 156 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

An evening scene captures a wooden deck adorned with string lights, providing a warm glow. A fire pit is centrally located, surrounded by outdoor seating. The cottage's pink exterior contrasts with the darkening sky, while a grassy area extends beyond the deck.

Guesthouse in Effingham

4.92 out of 5 average rating, 386 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 bronze statue of a seated figure can be seen on a brick walkway, facing a historic white building with a clock tower. Lush green trees frame the scene under a clear blue sky, creating a peaceful outdoor atmosphere.

Loft in Vandalia

4.94 out of 5 average rating, 270 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.

Guest favorite

Home in Brownstown

4.91 out of 5 average rating, 250 reviews

House By The Woods with hot tub 2 bedroom/sleeps 7

Hot tub on back patio until 7-6-25. We have 2 electric fireplaces, 1 bathroom, 2 bedrooms, futon & full size bed in living room that sleeps up to 7 total. It has a side outdoor covered porch with a seating area & table with chairs. Firepit area for roasting hotdogs or marshmallows. Firewood on premises. Propane grill on back patio. Small kids play area in front yard. Any bookings will have 10 am checkout

Top guest favorite

A comfortable living room features a large flat-screen television mounted above a stone fireplace. Light-colored sofas are arranged around a coffee table, with a decorative area rug anchoring the space. A chess set is displayed on a side table, and natural light enters through a nearby window.

Home in Vandalia

5 out of 5 average rating, 144 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.

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Popular amenities for Fillmore vacation rentals

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Other great vacation rentals in Fillmore

Top guest favorite

A sandy beach area is visible, leading to calm waters under a gentle sky. Swimming area signs are positioned along a pathway leading to the water. Several people can be seen enjoying the water, with distant greenery marking the shoreline.

Home in Keyesport

5 out of 5 average rating, 29 reviews

Vintage Lakeside Cottage in Keyesport

SarahRating, 5 stars2 weeks ago

The home was absolutely as described. Lovely, cozy decor. Everything felt clean. The important things were updated (bathroom, carpets, etc), but all the charming character was left in tact. I would definitely recommend this place to others. Be aware the town is VERY small. Two small restaurants with limited hours. (The one we went to - Hometown Cafe - was great though.) While the house is near the lake, it wasn't a fishable area for us without a boat. Thankfully Eldon Hazlet park was only 15 mins away, so we got our fishing/ nature fix over there. The home was great to come back and relax in. We spent most of Sunday inside due to rain and it was still a very pleasant weekend!

Top guest favorite

The entrance features an arched doorway with large glass panels, framed by classic red brick. Potted plants with vibrant flowers in hues of yellow and orange enhance the welcoming atmosphere. A plaque displaying the address is mounted beside the door.

Home in Louisville

4.98 out of 5 average rating, 52 reviews

State Bank Suite~ 1905 Historic Bank Brick Suite

ChrisRating, 5 stars2 weeks ago

Joshua is a great host. Incredibly communicative & the property was truly a hidden gem. We’ll be back.

Superhost

A firepit area features four dark wooden chairs arranged around a circular stone firepit, set in a gravel base. The surrounding greenery provides a natural backdrop, with lights positioned on either side of the seating area to enhance visibility during evening gatherings.

Cabin in Beecher City

4.84 out of 5 average rating, 19 reviews

Moccasin View peaceful paradise

SulaymanRating, 5 stars6 days ago

I only stayed for one day but it was great! There were a few cons such as the location being right off the road, some ants in the kitchen and ac dripping water in the bedroom. Other than those, the space was amazing. My favorite thing was the pond. It’s definitely worth the price!

Top guest favorite

A close-up view of a black chicken is featured, showcasing its prominent red comb and attentive gaze. In the background, a rustic chicken coop can be seen, surrounded by natural wood shavings and a fenced enclosure.

Home in Edwardsville

4.96 out of 5 average rating, 24 reviews

Cozy Chicken Cottage

HeatharlyneRating, 5 stars3 days ago

This place is charming, comfortable, and was perfect for my overnight stay. Emma is responsive and friendly. I would stay here again and highly recommend.

Guest favorite

A private balcony is shown with two white folding chairs and a small round table on a wooden deck. A street view offers glimpses of parked cars and the surrounding urban landscape.

Apartment in Greenville

5 out of 5 average rating, 17 reviews

Stay on the Historic Town Square in Greenville, IL

ShaRating, 5 stars1 week ago

Undoubtedly, the best AirBnB in Greenville! I wish she had 2 or 3 more properties, as I worry that one day it wont be available!

A serene landscape showcases a field of blooming yellow flowers amidst a wooded area, with a rustic log cabin partially visible in the background. The trees are bare, and the ground is covered with a mix of greenery and fallen leaves, creating a peaceful, natural setting.

Cabin in Vandalia

4.85 out of 5 average rating, 519 reviews

Sonnemann Cabin

KenRating, 5 stars1 month ago

We fell in love the moment we stepped inside. Definitely not for the hotel with the pool set, but was exactly what we wanted - a rustic log cabin from the historic past. It is set in the woods and wrapped with vines giving it a storybook feel. Paths are mowed through the woods to allow unobstructed walks surrounded by towering hickory trees and thousands of flowers. We will be back. Maybe again this summer, but for sure next spring when the dogwood trees and flowers are in full bloom. Thank you Bill, for making your cabin available. We would like to meet you next time to learn more about the history of the property.

Guest favorite

A covered patio area is shown with views of a serene pond lined by grassy banks. Decorative items, such as rocks and plants, are placed along the edges. Natural light pours in through the open sides, enhancing the connection to the surrounding country setting.

Home in Fillmore

4.95 out of 5 average rating, 39 reviews

Private Getaway House w/ Pond & Trails on 10 Acres

SusieRating, 5 stars2 months ago

Lovely place to stay off the beaten path.

Guest favorite

A spacious living area features a grey fold-out sofa bed with plush cushions, complemented by a bedside table. A full-length mirror reflects light from the nearby window. The open layout leads to a kitchenette and a private bathroom visible in the background.

Guesthouse in Hillsboro

4.73 out of 5 average rating, 11 reviews

Tree Top Retreat

GerardoRating, 5 stars1 month ago

Finding the cabin worked out very well. The location is close to the job and peace and quiet in Hillsboro. Lisa's response times were great to any questions that came up. Everything was nice, clean and accommodating.

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Vacation rentals in Fillmore

Top-rated vacation rentals in Fillmore

Vacation rentals for every style

Popular amenities for Fillmore vacation rentals

Other great vacation rentals in Fillmore

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