Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Top guest favorite

The cabin's exterior is viewed from a grassy area, showcasing a covered porch with steps leading up to the entrance. Two white doors are framed by light-colored walls, while a red wreath adds a touch of color. The natural surroundings feature trees in the background.

Cabin in Winchester

4.96 out of 5 average rating, 177 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

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, 364 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.

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, 506 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 residential street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows. Watch Netflix, Hulu, and Disney also.

Guest favorite

The living room and kitchen area features a mix of warm pink walls and natural light. A dining table with chairs is adjacent to a kitchen counter. A sofa bed is present, complemented by decorative pillows. Soft lighting is provided by an ornate chandelier.

Guest suite in Pittsfield

4.82 out of 5 average rating, 136 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, electric grill, screened in porch. ALL linens, towels, Bed sheets!!

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, 156 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, 724 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.

Guest favorite

The exterior features a basement-level entrance framed by a concrete pathway. Large windows provide natural light, while a well-maintained grassy area surrounds the entrance. The building's siding is light-colored, and a light fixture is mounted above the door.

Guest suite in Florissant

4.83 out of 5 average rating, 138 reviews

Peaceful lower level apt in wooded neighborhood

A self contained apartment located in the basement of our home. 2 private entrances, self check-in and check-out. The neighbors in our cul-de-sac are trees and cardinals (the birds not the baseball players.) Quiet enough to work, work, work. Spacious enough to play, play, play. Christian Hospital 6 min, Airport 17 min, Busch Stadium 24 min, Convention Plaza 24 min, Downtown St. Louis 25 min. Very near nature reserves and confluence of Missouri and Mississippi Rivers.

Guest favorite

A serene bedroom features a spacious bed with soft, muted linens and decorative throw pillows. Natural light filters through the room, illuminating the rustic wooden accents and century-old hardwood floors. A decorative bench sits at the foot of the bed, enhancing the cozy atmosphere.

Apartment in Carrollton

4.88 out of 5 average rating, 161 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

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, 110 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 treehouse-style rental is nestled among vibrant autumn foliage, with wooden steps leading up to the entrance. The structure features a private front porch, framed by surrounding trees and a gravel path, conveying a natural and serene atmosphere.

Guest suite in Dardenne Prairie

4.89 out of 5 average rating, 292 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh

Guest favorite

A peaceful view of a studio apartment situated behind a field of blooming yellow wildflowers. The house features multiple windows, reflecting a serene rural landscape, with trees and greenery in the background, enhancing the private and tranquil setting.

Apartment in Murrayville

4.97 out of 5 average rating, 420 reviews

Peace on the Prairie - Studio Apartment

This studio apartment is complete with full kitchen, bath, queen size bed, queen-size futon, a 50-inch smart TV with digital antenna reception, Netflix, and laundry facilities. Located on 24 rural acres of native prairie, forest, several ponds, and walking trails throughout, this is a great getaway to experience tranquility. Daily rental. Multiple day discount applied at booking. No cleaning fee.

Top 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

4.97 out of 5 average rating, 310 reviews

Pere Ridge Tree Escape

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.