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, 463 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.

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

ONE DAY ADVANCE BOOKING NOTICE! 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. 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

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, 141 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.

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, 154 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!

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, 341 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, 110 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.

Top guest favorite

A serene lakeside view features a gentle slope of green grass leading to calm waters. A hammock hangs between two trees, offering a resting spot. A birdhouse and small structure are visible nearby, complemented by lush vegetation surrounding the area.

Place to stay in Virginia

4.99 out of 5 average rating, 327 reviews

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!

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Popular amenities for Greenfield vacation rentals

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Free parking on premises

Air conditioning

Other great vacation rentals in Greenfield

Guest favorite

Two wooden swing benches are positioned under a covered area, providing a serene view of the river. Lush green trees surround the property, while a glimpse of tents can be seen in the background, creating a relaxed outdoor setting.

Cabin in Portage Des Sioux

4.95 out of 5 average rating, 40 reviews

Serene Cabin on the Mississippi River w/kayaking!

AngelaRating, 5 stars3 weeks ago

We loved our stay in the beautiful and peaceful location and cabin. The bed was amazing and the surrounding windows made you feel like you were in nature while offering amazing views. Can’t wait to return.

Top guest favorite

A wooden deck is shown with a railing and steps leading up to a door at the entrance. The brick wall of the building is visible, providing a textured backdrop. Sunlight casts shadows on the deck and steps.

Apartment in Auburn

4.98 out of 5 average rating, 40 reviews

Cozy days!

NancyRating, 5 stars5 days ago

Our stay was so relaxing. We were able to visit with family (only a block away). The beds were very comfortable. The host was amazing and caring. It was an amazing stay.

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

4.97 out of 5 average rating, 33 reviews

Cozy Chicken Cottage

EveRating, 5 stars1 day ago

we enjoyed our stay! it was very cute and cozy. we loved seeing the pigs and chickens.

Top guest favorite

Two outdoor chairs are positioned around a fire pit in a grassy area, surrounded by trees. The fire is actively burning, casting a warm glow. The ground is covered with fallen leaves, and the sky is illuminated by a sunset, enhancing the serene outdoor setting.

Home in Dow

5 out of 5 average rating, 18 reviews

Grafton Getaway @ The Studio

BlighRating, 5 stars3 weeks ago

Brandon’s place was perfect for our stay. Quiet and had all the amenities we needed. Bed was comfy, layout was just right for the two of us and the pup. The outdoor spaces are great and the record player is an awesome addition!

Top guest favorite

A stack of black towels is neatly arranged, each embroidered with the word 'Makeup' in white thread. The soft texture of the towels is visible, suggesting comfort and utility.

Guest suite in Dow

4.97 out of 5 average rating, 32 reviews

The Artist Suite | Enjoy Nature + Art

CurtisRating, 5 stars1 month ago

Very nice, quiet studio apartment.

Top guest favorite

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 stars2 weeks ago

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

Top guest favorite

Farm stay in Grafton

5 out of 5 average rating, 90 reviews

Historic Country Farmhouse on 80 Acres

AbbyRating, 5 stars2 weeks ago

It was such a great time at the homestead! It is such a lovely property. My friends and I had a blast. We wish we stayed longer! Patricia was a great host, thank you so much for everything- especially the waffle ingredients!!!🩷

Top guest favorite