Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Top guest favorite

The exterior of the cabin is displayed at dusk, showcasing a welcoming porch with seating. Soft lighting highlights the entrance, while ample greenery surrounds the structure. Gravel pathways lead to the cabin, enhancing the naturally serene setting.

Cabin in Winchester

4.96 out of 5 average rating, 163 reviews

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

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

4.98 out of 5 average rating, 462 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 street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows too. Also watch Netflix, Hulu, Prime, and Disney.

Top guest favorite

Two deer, one adult and one fawn, are seen standing in a grassy area beside a wooden fence. The lush greenery surrounding them emphasizes their natural habitat, while the soft sunlight highlights the gentle features of the deer.

Guesthouse in Jerseyville

4.97 out of 5 average rating, 139 reviews

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

Guest favorite

A collection of decorative items rests atop wooden cabinets. Two ceramic roosters and a chicken figurine are positioned on either side of a vintage-style 'Farm Fresh' sign, which features an image of a rooster. The warm wood tones enhance the rustic decor.

Home in Winchester

4.91 out of 5 average rating, 140 reviews

Winchester Guest Cottage

The Winchester Guest Cottage is a chance to experience the past while still enjoying the comforts of modern living. Guest will appreciate the living history of this mid 1800s home with much of its original architecture still intact. Enjoy the natural light from the tall windows while peering out through much of the original wavy glass. Most of the homes original wood work, doors and fireplace mantel are still there as they were in the 1800s. The floors were repurposed from WHS in the 1950s.

Guest favorite

A table is covered with a patterned tablecloth, featuring a stylish UV lamp. The lamp emits a blue light and is positioned next to a decorative plant, enhancing the table's setup in the inviting space.

Guest suite in Pittsfield

4.82 out of 5 average rating, 134 reviews

Florence Guest House--Loft Unit

Upper Loft Unit is the top floor of the guest house. With it's own entrance & deck area, No Interaction (if desired) from the lower unit is possible. Loft Supplies: Living room/kitchen area, private bathroom, large bedroom with 2 twins/1 full bed (Fitted Bed spreads). Deck with an amazing view of the area. Guests DO HAVE FULL USE of the large yard. Guest House Has: Parking area, two Illinois river lots, charcoal grill, screened in porch. ALL linens, towels, Bed sheets!!

Top guest favorite

A cabin porch is framed by green and white paneling, featuring a welcoming front door and a decorative wreath. Outdoor furniture includes a swing and picnic table. The surrounding yard is lush and green, with views of the field in the background under a clear sky.

Cabin in Carrollton

4.92 out of 5 average rating, 137 reviews

Graham Farm Cabin

Enjoy the country life in rural Greene Co in our cabin located on our farm. A great getaway spot! Features 2 bedrooms, 2 bathrooms, kitchen, dining, living room, laundry, porch and fire pit. Look out over the field for a beautiful sunrise. On a clear night, the stars are amazing! Enjoy nature and take a walk along our creek. Spend some time in our little town at our local shops and restaurants.... We live in the country between Carrollton and Jerseyville. (There is no WiFi.)

Guest favorite

A spacious sleeping area features a wooden bed frame with a light-colored bedding set. Decorative elements include wall art and a large mirror. Natural light enters through windows dressed in light curtains, highlighting the hardwood floors throughout the room.

Apartment in Carrollton

4.88 out of 5 average rating, 153 reviews

Farmhouse Loft

Experience the life and hospitality of a quintessential small town - Carrollton, Illinois. A historic community located just off the beaten path, Carrollton convincingly captures the spirit of rural America. Inspired by the peaceful charm of country life, we showcase century-old hardwood floors, exposed brick walls and thoughtful design. Farmhouse Loft is a charming retreat on the historic courthouse square --enjoy life in a loft apartment overlooking the courthouse lawn!

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, 135 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

Townhouse in Murrayville

4.98 out of 5 average rating, 306 reviews

Peace on the Prairie Too - Tiny House

Need a break from Politics? Peace on the Prairie accepts all guests for who they are rather than what some might wish them to be. Whether it’s a business trip, romantic time together with your significant other, a family vacation, a girl's time away, a secluded spot to work on your music, writing, art, star gazing, or a reconnection with nature, you'll find your inspiration and renewal in this natural rural setting of 23 acres of restored prairie, timber, and wetlands?

Top guest favorite

An antique cast iron soaking tub is situated on a wooden deck, enclosed by a yellow picket fence and decorative curtains. A wooden shelf is mounted on the fence, with natural elements visible in the background adding to the peaceful outdoor setting.

Cabin in Jacksonville

4.97 out of 5 average rating, 340 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.

Guest favorite

A set of vintage double doors features a soft blue-green hue and tall, arched glass panels, allowing light to filter through. The doors are mounted on a rustic sliding track, complementing the warm wooden flooring beneath.

Loft in Winchester

4.97 out of 5 average rating, 122 reviews

The Bike Flat

Visit historic Winchester and explore what our quaint community has to offer! This stylish place to stay is perfect for a quiet getaway and can accommodate groups thanks to its ample space. You can bring the family or plan a getaway with friends. The flat is located above a newly opened bicycle and coffee shop that also offers craft beers and wine. We hope you will consider choosing our rural accommodations for a trendy and relaxing experience!

Guest favorite

A wooden sign, shaped like a barrel, displays the name 'The Campground Guest House' with an arrow pointing left. Surrounding greenery features lush plants and trees beneath a clear blue sky, creating a welcoming first impression of the property.

Home in Carlinville

4.97 out of 5 average rating, 109 reviews

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.

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Other great vacation rentals in Greenfield

Bungalow in Carlinville

5 out of 5 average rating, 10 reviews

The Carlinville Sunset Bungalow

ElizabethRating, 5 stars3 weeks ago

Having stayed in Carlinville many times this has been one of my favorite places. Beds were comfortable and generous. Bathrooms were nice and clean. The location was very convenient to the train station and the square, close enough that I could easily walk down and get coffee in the morning. It is on a relatively busy street (for Carlinville) and you can hear the train. This is not something that bothered me and I had no issues sleeping. Would definitely consider for the next time I'm in town.

The exterior of a brick building features a warm wooden door with an intricate glass panel, beneath a small white overhang. A decorative planter with greenery is positioned beside the entrance, while the address is displayed prominently on the wall.

Apartment in Winchester

4.97 out of 5 average rating, 68 reviews

The Primrose inside historic commercial bldg

Jason,Darrin,ClayRating, 5 stars1 month ago

Debbie is a fantastic host and her place was just as advertised. I would recommend 10/10

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, 28 reviews

Cozy Chicken Cottage

BillRating, 5 stars2 days ago

Emma's cottage was beautiful and exactly as described. We found it to be charming and felt like "home" She provided some soda/pop, water and light snacks. The outside area was amazing, lovely seating areas. The chickens are are pretty cool and the pigs Corona and Modelo are adorable. Emma stopped outside while we were walking around and let us know that if you say their names they come out of the barn. Truly enjoyed our 1 night stay and already looking forward to a future visit.

Superhost

A wooden deck is presented, featuring a covered grill and a dining table surrounded by several metal chairs. Lush green trees and calm water are visible in the background, creating a serene outdoor space, suitable for relaxation.

Home in Mount Olive

4.96 out of 5 average rating, 28 reviews

Relaxing Fishing Cabin

JamesRating, 5 stars2 days ago

Peaceful and private along a small lake. Really enjoyed sitting on the porch watching wildlife. All the ammenities you would want.

A bathroom features a floral patterned shower curtain, complementing the green plaid wallpaper. A white pedestal sink is seen next to a storage shelf with decorative items. A soft rug lies on the wooden floor, and warm light spills from a lamp beside the sink.

Apartment in Bunker Hill

5 out of 5 average rating, 24 reviews

The Loft

CoryRating, 5 stars1 week ago

Super cute, cozy place. Would definitely book again when making a trip out to this area!

A view from a window shows the historic Pike County Courthouse across the street, featuring a prominent clock tower. Soft white curtains partially frame the view, allowing natural light to brighten the interior while providing a glimpse of the green lawn in front of the building.

Loft in Pittsfield

4.91 out of 5 average rating, 70 reviews

Historic Loft on Adams

NicolasRating, 5 stars1 week ago

Great place to stay situated right next to the owner's restaurant. food was great as well. Included recommendations for local spots to go

A serene view of Pittsfield Lake is framed by lush greenery, showcasing calm waters reflecting the surrounding trees. Soft sunlight filters through the leaves, creating gentle highlights on the surface of the lake.

Home in Pittsfield

4.86 out of 5 average rating, 14 reviews

Roots Lodge at Pittsfield Lake (Starlink Internet)

JasonRating, 5 stars5 days ago

Cozy home

An interior view of a cabin showcases wooden paneling and a vaulted ceiling. A cozy niche with a mattress is centered under a large window, allowing light to enter. Two beds with wooden frames are positioned on either side of the room, creating a rustic atmosphere.

Cabin in Calhoun County

4.96 out of 5 average rating, 23 reviews

Indian Springs Cabin.

TimRating, 5 stars3 weeks ago

Very nice get away for a weekend! We would absolutely love to go back. Close enough to a few small towns but far enough away to enjoy the peace and quiet.

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Vacation rentals in Greenfield

Top-rated vacation rentals in Greenfield

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