Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Top guest favorite
The lodge is positioned atop a grassy hill, showcasing a blend of brick and wood exterior. Large windows reflect the surrounding greenery. An American flag stands proudly, with manicured lawn leading up to the entrance, offering a spacious and welcoming appearance.
Home in Godfrey
4.94 out of 5 average rating, 116 reviews

Grafton Getaway @ The Lodge 8,000 sq ft/sleeps 35

Grafton Getaway @ Overlook Lodge is a secluded 33 acre property overlooking Lockhaven Public Golf Course and the Mississippi River Valley. This one a kind property sleeps 35 and sits on a hilltop at the end of the road with a private Lake and pond. At all 8 Getaway locations we hope to host your next couples, family, or group getaway or special event (5 weddings in a row in 2025). The Lodge is 12 minutes from Grafton, IL and 40 minutes from STL airport. Brandon Jeffers - founder/owner/operator

Guest favorite
A charming country house is set on a green, grassy lot, featuring a front porch with two steps leading up to the entrance. An American flag is displayed on the porch. Surrounding trees provide shade, and the peaceful landscape showcases open fields.
Home in Medora
4.87 out of 5 average rating, 69 reviews

country living

this is a country house. enjoy out door living in the country. watch longhorn cattle from back yard, take hikes, ride bicycles, provided, watch stars at night while roasting s'mores over bonfire. make 1 breakfast with longhorn breakfast sausage. spend a peaceful weekend together away from the city. no phone (service is available if u still want technology), no wifi. decompress away from technology. please read all sections. Also, we live on the property in case you have questions

Top guest favorite
A cozy cabin is nestled among tall trees, featuring a welcoming front porch and a green door. The surrounding lawn is well-kept, with open fields visible in the distance, creating a peaceful and serene setting.
Guesthouse in Jerseyville
4.96 out of 5 average rating, 200 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.

Top guest favorite
The interior of the cabin features exposed wooden beams and reclaimed logs, creating a rustic aesthetic. A comfortable sofa is positioned in front of a brick fireplace, which is flanked by a dresser. A small dining table and chairs occupy one corner, with a cozy area rug enhancing the warmth of the space.
Cabin in Jacksonville
4.97 out of 5 average rating, 787 reviews

Audrey's Abode

Audrey’s Abode is just the place you have been looking for to relax and reconnect with family, friends, nature and a simpler time. Located on a 7 acre hobby farm just south of Jacksonville, Illinois (30 minutes west of Springfield), Audrey’s Abode is a fully restored historic log cabin with all the modern amenities for a comfortable getaway. Need additional space? Check out our other listing next door - Bunkhouse Seventy-Four. Pets are welcome but we charge a $35 pet cleaning fee.

Top guest favorite
The cabin exterior is displayed, featuring a large, covered porch with a swing and seating area. The structure is surrounded by lush green grass and trees, highlighting its rural setting. The roof is gabled, and the siding is a combination of white and green.
Cabin in Carrollton
4.93 out of 5 average rating, 151 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.)

Top guest favorite
A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.
Cabin in Brighton
4.97 out of 5 average rating, 117 reviews

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

Guest favorite
A charming yellow exterior of the home is highlighted by a metal roof. A welcoming front porch features a bench and two chairs, surrounded by well-maintained greenery and a grassy area. Large windows allow natural light to fill the interior spaces.
Home in White Hall
4.91 out of 5 average rating, 113 reviews

The Humble Hideaway

Escape the hustle and bustle in our charming backyard oasis, just a short walk from Main Street. This private home offers a cozy patio, and all the comforts of home including a fire pit and dining table. The home itself is bright and airy with hardwood floors, and a new central air conditioning. Curl up on the plush sofa and enjoy the flat screen smart TV in the main living area or prepare a meal in the fully equipped kitchen with brand new appliances.

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, 162 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.

Guest favorite
A cozy living area features a black sofa with decorative pillows and a wooden coffee table at its center. Natural light streams through two windows, illuminating the neutral tones and textured decor. A small accent chair and a patterned rug complete the inviting space.
Loft in Winchester
4.92 out of 5 average rating, 186 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!

Top guest favorite
The image depicts a traditional red brick home with a single-story design. A large tree is observed in the background, surrounded by open grassy areas. Snow remains on the ground, contrasting with the clear blue sky above.
Farm stay in Carrollton
5.0 out of 5 average rating, 53 reviews

Peaceful Country Stay- The Carrollton Farmhouse

Slow down and settle in at The Carrollton Farmhouse—a traditional red brick home with fresh farmhouse style, set on peaceful acreage. Whether you’re gathering with family, visiting for a wedding at Walnut Hall Estate, or looking for a quiet retreat after a day of hunting, this home offers comfort and calm in the heart of the countryside. Spend your evenings around the fire, sharing stories under the stars.

Guest favorite
A modern studio cabin is elevated on pillars, surrounded by lush greenery. The exterior features dark wood siding and multiple windows, allowing natural light to illuminate the interior. A deck is visible, indicating outdoor space for relaxation.
Farm stay in Grafton
4.95 out of 5 average rating, 370 reviews

Pere Ridge Tree Escape with private hot tub

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.

Top guest favorite
A two-story tiny house is positioned at the end of a grassy path, surrounded by native grasses and trees. A rainbow flag gently waves in the breeze, and several trees display autumn foliage, adding color to the serene landscape.
Townhouse in Murrayville
4.98 out of 5 average rating, 357 reviews

Peace on the Prairie — Quiet Nature Retreat

Peace on the Prairie Too is a thoughtfully designed two‑story tiny house set on a 24‑acre restored prairie, offering the kind of quiet, space, and natural beauty that’s hard to find anywhere else. Whether you’re here to unwind, create, reconnect, or simply breathe a little deeper, this tiny house gives you room to slow down without giving up comfort.

Popular amenities for Greenfield vacation rentals