Vacation rentals in Milan

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Top-rated vacation rentals in Milan

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Top guest favorite

The exterior of a rustic cottage is shown, featuring a welcoming porch with two metal chairs. Lush greenery surrounds the entrance, and a path leads to the front steps. The building has a light-colored facade and a classic metal roof, set against a peaceful rural backdrop.

Guesthouse in Bradford

Spacious and Private Guesthouse in the Country

Rustic, refined cottage with all amenities. 1930s farm home updated for modern life. Soak in the peace and quiet. Perfect for EXTENDED STAYS (CHECK DISCOUNTS!), artists/writers, looking for quiet inspiration. Full kitchen, Keurig coffee-maker, washer/dryer, stereo. Unlimited Internet through local company (TEC). Central heat/ air. Large screen TV w/ Amazon Prime. No smoking or pets, please. No minor children. Adults only. Very Private backyard. Welcome persons of all beliefs & backgrounds.

4.93 out of 5 average rating, 142 reviews

Guest favorite

A covered front porch features two yellow rocking chairs positioned next to a small round table. A striped outdoor rug lies beneath them. Lush plants are placed in decorative pots, enhancing the welcoming atmosphere of this vintage bungalow.

Bungalow in Milan

The "Heart of Milan" Guest House

This is a vintage 1920's craftsman style bungalow that has recently been redecorated. You will be renting the whole house to include a large master bedroom, a second private bedroom, two bathrooms, a fully equipped kitchen, office, living space and common room with an extra twin bed. Washer and dryer included. Hardwood floors throughout the home. This house is an ideal rental for executives or travelers who are looking for a more home like environment or anticipate an extended stay.

4.97 out of 5 average rating, 462 reviews

Top guest favorite

Home in Medina

The Cedar Hill Retreat

Welcome to our newly renovated 2-bedroom, 1-bath Cedar Hill Farmhouse Retreat! Perfectly situated just 5 minutes from charming Downtown Medina, 15 minutes to North Jackson, and 20 minutes to vibrant Midtown. Sleeps 6 in cozy, stylish spaces. Sip your morning coffee on the patio, watch goats and cows graze, listen to songbirds, and unwind by the fire pit under starry skies. Perfect for a weekend escape, family gathering, or local event — soak up peaceful country charm with easy city access.

5.0 out of 5 average rating, 70 reviews

Top guest favorite

A comfortable open-plan sleeping area features two queen-size beds with dark upholstered headboards, complemented by soft white linens and green accents. A wooden dresser with decorative lamps and a mirror adds elegance. Large windows provide natural light, framed by light curtains.

Cabin in Humboldt

Crown Cottages - Double Queen

Take it easy at this unique and tranquil getaway. Enjoy all that Crown Winery and West Tennessee have to offer from our great location nestled within the beautiful Tuscan-inspired Crown Winery property. You'll be joining us at our cottage nestled at the base of our breathtaking vineyard. Wake up to the stunning view of the wind blowing through the vines and "wine down" with a walk up the hill to see the sun set over the back vineyard. This 600-square-foot free-standing cottage sleeps four.

4.95 out of 5 average rating, 63 reviews

Guest favorite

A single-story home features a well-maintained exterior with light-colored siding and a neatly trimmed lawn. The attached garage has space for vehicles, while a decorative element is placed near the entrance. The inviting front yard is shaded by mature trees against a clear blue sky.

Home in Jackson

Cozy Modern Minilmalist Stay in North Jackson

Welcome to my home in the peaceful northernmost part of Jackson, Tennessee. Our cozy and comfortable home is ideal for families, solo travelers, or business guests seeking a serene retreat with easy access to everything Jackson has to offer. This inviting space features 3 bedrooms, 2 bathrooms, Wi-Fi, smart TV and an array of kitchen utilities. Whether you’re here for a short stay or an extended visit, you’ll find everything you need for a comfortable and relaxing experience.

4.92 out of 5 average rating, 83 reviews

Top guest favorite

A close-up image of a Nigerian Dwarf goat features soft brown and black fur. The goat’s bright eyes and gentle expression indicate curiosity. The background consists of blurred greenery, enhancing the goat's presence in its natural environment.

Cabin in Huntingdon

Cottage A at Dry Hollow Farm

Local Amish builders constructed this cabin at Dry Hollow Farm in 2021. We raise dairy goats, luffa gourds, and herbs which we incorporate into our handcrafted products. We are located five miles outside of Huntingdon, Tennessee, a rural small-town setting, We offer a peaceful rural setting with plenty of space to roam, a Soap Shop for perusing our products, Herb Shack for plant shopping, dogs for petting, and some time spent away from the street of everyday life.

4.99 out of 5 average rating, 269 reviews

Top guest favorite

A fire pit is surrounded by a stone ring, with flames actively burning. A wooden chair faces the serene lake, framed by lush green trees and reflecting sunset hues. The tranquil water glimmers in the evening light, creating a peaceful outdoor setting.

Apartment in Trenton

Cozy apt suite/lakefront/pool /near TN Safari Park

Take a break from your hectic lifestyle & experience tranquility on our private A walk out basement guest suite with private entrance. Includes den w/ wood burning fireplace, (futon mattress ) 1 bedroom (queen mattress), bathroom w/ shower, kitchenette on a private 50ac lake. Amenities include gas grill, swimming pool , kayaking, hammock, fire pit, fishing off dock or use of jon boat. 2 miles from Gibson Co. Lake & 30 min from TN Safari Park & Discovery Park

4.87 out of 5 average rating, 116 reviews

Top guest favorite

A living area features two brown leather sofas adorned with patterned cushions, positioned around a wooden coffee table. A modern kitchen area is visible in the background, with white cabinetry and ample natural light.

Home in Westport

The Brandon House, Modern Country Retreat

Forget your worries in this spacious and serene space. Newly renovated home. Conveniently located within 15 minutes of I-40, 1 hour 45 minutes between Nashville and Memphis. Located within 15 minutes of Natchez Trace State Park, Southland Safari and guided Tours, The Dixie Performing Arts Center, Buttrey Wedding and event space, and many other attractions. Hiking, hunting, and fishing close by.

5.0 out of 5 average rating, 210 reviews

Superhost

A spacious living area features a comfortable gray sectional couch and a blue chair, accented with patterned cushions. A round coffee table sits on a decorative rug, while natural light filters through windows, illuminating wall art and a large mirror. Greenery adds a touch of warmth.

Home in Jackson

The Tinker Retreat

Enjoy all the things Jackson has to offer within minutes of this home. Whether your looking for a good nights rest or a fun family game night, The Tinker Retreat is ready to accommodate. Step inside, leave your troubles at the door and relax in our massage chair or catch a game of foosball while enjoying some freshly popped popcorn. This home offers something for everyone to enjoy!

4.91 out of 5 average rating, 207 reviews

Guest favorite

The exterior of a cabin is shown, featuring a red metal roof and wooden siding. A spacious porch with decorative items enhances the entrance. Surrounding greenery and a gravel path are visible, alongside a riding equipment stand. Horses are seen nearby, adding to the ranch atmosphere.

Cabin in Cedar Grove

Cowboy Hideout 14 miles from I-40

Take it easy at this cozy cabin tucked in the woods at the Southern Serenity Horse Ranch. Bring your horses, ride the trails. Sit for hours around the fire pit. Enjoy the comfortable bed. Cook in the well stocked kitchen in your cabin named Cowboy Hideout. Soak up everything Tennessee Walking Horse. You will never want to leave this beautiful spot once you arrive.

5.0 out of 5 average rating, 10 reviews

Top guest favorite

A single-story home is displayed, featuring a light-colored exterior with multiple windows. The property is set on a well-maintained lawn, bordered by shrubs. A paved driveway leads to the entrance, and trees provide a backdrop, suggesting a quiet neighborhood.

Home in Trenton

Simply Tea-rrific

"Quiet, cozy 3-bedroom home with 1.5 baths, nestled in a peaceful neighborhood. Centrally located in the heart of town, enjoy easy access to local amenities, charming shops, and scenic walks. Relax in the spacious backyard with a firepit—perfect for family gatherings or unwinding after work. An ideal spot for both family stays and business trips."

5.0 out of 5 average rating, 34 reviews

Top guest favorite

The spacious living area features large windows allowing natural light to illuminate the room. A vintage American flag hangs on one wall, while a wooden dining table with two chairs sits near the kitchen island. A comfortable sofa is positioned across from a shelving unit filled with books and decor.

Loft in Huntingdon

Loft 163

Loft 163 is located on the Court Square in Downtown Huntingdon TN. It's on the second level of a newly renovated historic building that dates back to the late 1800's. It has amazing views and is in walking distance to The Dixie Performing Art's Theatre, Court Theatre, restaurants, coffee shop, gift shops, and more.

4.98 out of 5 average rating, 331 reviews