Vacation rentals in Milan

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Top-rated vacation rentals in Milan

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Top guest favorite

Cottage in Huntingdon

Marie’s Cottage Off Main – Walk to Downtown

Welcome to Marie’s Cottage Off Main — a beautifully restored folk Victorian retreat tucked just steps away from downtown Huntingdon where you can visit local restaurants, shops, and the Dixie Carter PAC. Built in 1880, this 2-bedroom, 2-bath cottage blends historic charm with modern comfort. Whether you’re here for a peaceful getaway, visiting family, or exploring West Tennessee, you'll find a cozy, thoughtfully curated space that feels like home. Equipped with a full kitchen and spacious patio.

5.0 out of 5 average rating, 42 reviews

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, 146 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, 469 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, 74 reviews

Top guest favorite

Home in Jackson

Daisey’s Homeplace

We hope you enjoy this restful, comfy 3 bedroom/2bath home filled with beautiful antiques along with all the amenities you need. It has 4 smart TVs, fenced in back yard with private patio to sit, covered parking, and board games for the whole family. It is located in North Jackson with many restaurants and shopping centers nearby. Daisey’s Homeplace is in honor of where we found and rescued our second dog, Daisey, who desperately needed a family to care for her. Come and stay with us!

4.97 out of 5 average rating, 100 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, 85 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, 274 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

Superhost

Home in Jackson

Charming 3 Bedroom House Minutes from Downtown

Centrally located on Highland Ave., this three bedroom home is minutes from Jackson's quaint Downtown, the Carl Perkins Civic Center, The Ned, Jackson Madison County General Hospital, the Jackson mall and much more. Jackson, the Hub City and birthplace of Rockabilly, is a wonderful base from which to explore West Tennessee and Northern Mississippi, including Shilo, Parker's Crossroad, the Loretta Lynn Ranch, Tennessee Safari and so much more.

4.86 out of 5 average rating, 309 reviews

Top guest favorite

Tiny home in McKenzie

Cozy Poolside Cottage

Sleeps 4 Welcome to your own private getaway! This charming 500 sq. ft. pool cottage offers comfort, privacy, and convenience with a separate entrance—perfect for couples, small families, or business travelers. One cozy bedroom with a queen bed. Spacious living area with a sleeper sofa (sleeps 2). One full bathroom with fresh linens and toiletries. Full kitchen which includes a refrigerator, stove, and microwave.

4.99 out of 5 average rating, 71 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, 212 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, 11 reviews