Vacation rentals in Madison

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Top-rated vacation rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Townhouse in Brandon

4.95 out of 5 average rating, 125 reviews

Cheerful 3 Bedroom Duplex. Close to water

Bring the whole family to this great house close to Ross Barnett Reservoir, walking distance to Lakeshore Park, Pelahatchie shore park with boat launch access & frisbee golf course. The property is pet friendly but there is a pet fee Waking distance to grocery stores, Spirit stores, and restaurants. Within the facility of Madison ,Ridgeland, Flowood This is a duplex home & I also have the 3 bedrooms 2 bathe next door to this home& it to is on Airbnb just check my profile for another listing

Guest favorite

Rental unit in Jackson

4.97 out of 5 average rating, 126 reviews

*Cozy ~Hide ~Away* Comfort, Clean & Convenient

Clean!🧹🏡Our Space has EVERYTHING you NEED😊 Sleep endlessly in our super comfy king size bed 🛌, enjoy FREE💨 high speed WIFI, NETFLIX, DISNEY, HULU & ESPN+ or just relax on our private patio. We furnish our units with your comfort in mind & cleanliness is our Top Priority! No stairs to climb and a conveniently covered assigned parking space makes every trip to your vehicle hassle free. Just a couple of steps from the poo 🏊‍♀️l & gym🏋‍♂️. Private gated community awaiting your arrival!

Guest favorite

Guesthouse in Raymond

5 out of 5 average rating, 104 reviews

Charming, Peaceful Cottage

Ready to get away from it all? Come stay at Dove Cottage, a tiny space, fully furnished with everything you would need or want with great views of a beautifully landscaped yard that we call “The Park”. Rest and relax on the front porch. Take a bike ride or walk through the historic town of Raymond. This guest house is close to the Natchez Trace and only a half hour from all the Jackson area attractions. A fire pit with s’mores and free breakfast are included. Come see for yourself!

Guest favorite

Guesthouse in Brandon

4.99 out of 5 average rating, 642 reviews

The Cottage on College Street

The Cottage is very cozy with a mixture of vintage and industrial decor. Visitors will have complete privacy within the house at all times, but with our home close by, we are always happy to help should you need anything! We are located in Downton Brandon in the Historic District. The Cottage is a guest house seated behind our home; it is a very quiet place, and it is great for working individuals, couples seeking a fun concert experience, or families participating in ball tournaments.

Guest favorite

Guesthouse in Jackson

4.99 out of 5 average rating, 103 reviews

Relax in Architecture! Secluded, Safe, and Serene.

Welcome to the Falk House! Listed on the National Register of Historic Places by the US Department of the Interior, the Falk House is a treasure of mid-century modern design. We've transformed the original art studio into a stylish, private oasis, with expansive views of nature and Eastover’s Upper Twin Lake. You will be central to all metro destinations, including amazing restaurants, bars, and shopping, as well as area hospitals, courts, and businesses. Long stays ideal.

Guest favorite

Guesthouse in Madison

4.96 out of 5 average rating, 134 reviews

Mannsdale Manor Bunk House

Sweetest lil Bunkhouse in the South and in the safest little city in America according to Forbes Magazine. Nestled in the pines, our guests have privacy in nature with the amenities of rural life. Our location is central to the Madison-Jackson area; easy access to shopping and fine dining; tons of charm and character; full access to pool, private patio. Ask me for special discounts for Active military, Veterans, Law Enforcement and Southwest Airline employees. Contact Pam.

Guest favorite

Cottage in Jackson

4.94 out of 5 average rating, 715 reviews

The Funky Monkey Cottage in Fondren!

The Funky Monkey is a cozy, whimsical, historic cottage brimming with charm in the heart of Fondren! The perfect spot for a quiet romantic weekend, a last-minute getaway, or a family trip to the famous Hal's St. Paddy’s day parade. Within walking distance to local restaurants, coffee shops, boutiques, and music venues and a short drive to all major medical facilities, universities and museums. The Funky Monkey Cottage is the most unique spot for your Jackson adventure!

Guest favorite

Home in Pearl

4.98 out of 5 average rating, 125 reviews

Modern Farmhouse + Gameroom&Close to Everything!

Newly remodeled farmhouse in the perfect location. Fully stocked kitchen, on site laundry, outdoor gathering with fire pit. The game room has pool table, arcade games, karaoke machine, and extra large projector. Perfect location within 15 minutes of Downtown Jackson, outlet mall, Mississippi Braves, Brandon Amphitheater, golf courses, JAN airport, Tesla, several museums, & more. If you need a car, we can accommodate you through Turo. Just message us for availability.

Superhost

Guest suite in Jackson

4.77 out of 5 average rating, 233 reviews

Magnolia Suite*Private Entry, OldCanton N. Jackson

You'll love the feel of our newly renovated private suite. It offers 100% privacy with a self check-in keypad and a private entrance at the front. Enjoy the 30-years old magnolia trees that savor sweet floral fragrance along the crafted walkway during Spring and Summer. Less than 3mins drive to city restaurants, markets and recreational places like Ridgeland NorthPark mall, Bridges Park and Tennis Center. It's secured, quiet and respectable neighborhood.

Guest favorite

Guest suite in Belhaven

4.96 out of 5 average rating, 896 reviews

Jewelbox Suite w/ Private Entry - Perfect Locale

The Snooty Suite loves everybody! Smack in between downtown and Fondren (but in an awesome, old historic neighborhood in its own right), it's part of the House of Seven Gables. With a private entry, sitting room and bath, you'll have ample breathing room and the freedom to explore Jackson at your leisure. Chill on the porch, walk to the coffee shop or take a quick drive to Fondren, downtown and the museum campus.

Guest favorite

Home in Jackson

4.84 out of 5 average rating, 130 reviews

Newly Renovated Townhouse Suite in City w/ Soul

You will be close to everything when you stay at this centrally-located home. Jackson is a soulful kind of place for a weekend getaway, family fun, group tour, reunion, convention or small business meeting. Explore 29 unique museums and attractions, over 300 restaurants, annual events and festivals, three historic cultural districts, innumerable visual and performing arts and cool nightlife.

Guest favorite

Home in Fondren

4.93 out of 5 average rating, 450 reviews

Top of Fondren

Located in the Historic Fondren District, my place is just steps from fabulous restaurants, wine bars, coffee shops, shopping, music venues (Duling Hall), and a grocery store (Corner Market). It is also very close to University of Mississippi Medical Center, Baptist Hospital, Millsaps and Belhaven University. Enjoy private/off street parking in the bustling downtown Fondren District.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Madison vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Madison's top sights

Renaissance at Colony Park33 locals recommend

Kroger30 locals recommend

Malco Grandview Cinema16 locals recommend

Cock of the Walk15 locals recommend

Natchez Trace Multi-Use Trail13 locals recommend

Pelican Cove Grill12 locals recommend

Other great vacation rentals in Madison

Guest favorite

Home in Ridgeland

5 out of 5 average rating, 30 reviews

Guest Favorite - Cozy Fun near Huge Lake

Guest favorite

Home in Brandon

5 out of 5 average rating, 7 reviews

Cozy bed in breakfast feel

Guest favorite

Tiny home in Brandon

4.92 out of 5 average rating, 25 reviews

ABIDE…. A place to dwell

Guest favorite

Guest suite in Jackson

5 out of 5 average rating, 9 reviews

Luxe Condo in great area with House Water Filter.

Guest favorite

Home in Brandon

4.91 out of 5 average rating, 34 reviews

Waterfront Rez Retreat 4BR w/boat slip & pier

Guest favorite

Home in Flora

4.88 out of 5 average rating, 69 reviews

Betty's

Guest favorite

Cabin in Raymond

5 out of 5 average rating, 24 reviews

Walden@Raymond

Guest favorite

Guesthouse in Brandon

4.92 out of 5 average rating, 49 reviews

Guest House

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Quick stats about vacation rentals in Madison

Total rentals
10 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
510 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Reservoir Overlook, Renaissance at Colony Park, and Old Trace Park

Vacation rentals in Madison

Top-rated vacation rentals in Madison

Townhouse in Brandon

Rental unit in Jackson

Guesthouse in Raymond

Guesthouse in Brandon

Guesthouse in Jackson

Guesthouse in Madison

Cottage in Jackson

Home in Pearl

Guest suite in Jackson

Guest suite in Belhaven

Home in Jackson

Home in Fondren

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Other great vacation rentals in Madison

Home in Ridgeland

Home in Brandon

Tiny home in Brandon

Guest suite in Jackson

Home in Brandon

Home in Flora

Cabin in Raymond

Guesthouse in Brandon

Quick stats about vacation rentals in Madison

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore