Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Top guest favourite
A living area is showcased with warm wooden walls and terra cotta tiled floors. A cozy sofa is paired with a rustic coffee table. A kitchen island with a countertop is visible, along with a window that allows natural light into the space.
Guest house in East Nashville
4.97 out of 5 average rating, 920 reviews

Luxurious Cozy Guesthouse

This space is completely private and separate from the main residence. It has a king size bed, bathroom with shower, full kitchen, and living area with flat screen and cable. Vaulted ceilings with thick wooden beams give the apartment a spacious feel. The floor is done in a terra cotta Mexican tile; the decor is bright and funky. French doors open to a private courtyard area connected to covered parking. It's located in historic Inglewood/East Nashville. The quiet neighborhood is covered with mature trees and is just one block from the Cumberland River. It feels like you are far from the big city, but in reality, you are minutes from Opry Mills and downtown Nashville. Hip restaurants, coffee shop, pub, and public transit are just blocks away. **We are huge child and animal lovers, but our space is not safe for children. We have a no child under 12 policy, and a not pet policy. Sorry for any inconvenience this may cause.

Guest favourite
A charming two-story house sits on a well-maintained lawn, framed by trees. The front porch, with steps leading up, enhances curb appeal. A gravel driveway accommodates parking, and a separate building is visible nearby, ensuring a peaceful setting.
Home in Madison
4.92 out of 5 average rating, 242 reviews

Blissful Boho Chic Two Bedroom Main Level

Enjoy your own space away from the hustle and bustle of Nashville, but still close enough to hit all of your favorite places. This two bedroom two bath is perfect for your family or group of friends. 2 Queen Beds 1 Blow up Mattress (upon request) Downtown is 25min East Nashville is 20min 12 South is 23min LGBTQIA+ friendly. BLM. Veteran owned. This is a safe space for ALL. *Note: there is another unit on site, so no loud parties are allowed. IF you need an event look at other listing.

Top guest favourite
The interior of the cottage features a cozy sleeping area with a spacious bed dressed in soft linens. Wooden walls provide warmth, while rustic decor enhances the vintage charm. A kitchenette is visible in the background, and natural light enters through the windows.
Cottage in Madison
4.95 out of 5 average rating, 881 reviews

Recharge and Renew in a Preserved Historic Cottage

Breathe healthy in this hypoallergenic environment. Stay warm around a central stone fireplace and soak up the cultural significance of staying in a carefully restored domestic cottage listed on the National Register of Historic Places. Enjoy a soak in the hot tub to relax a little more. This original tiny house has no separate bedrooms. Spa is near the main house-70 feet from the cottage. Swim wear required. It is private for the cottage guests only. We are 7 miles from downtown Nashville.

Guest favourite
A charming brick home is set amidst a lush green lawn, highlighted by mature trees and carefully tended flower beds. The entrance features a welcoming pathway, leading to large windows that invite natural light into the living space.
Cottage in Madison
4.9 out of 5 average rating, 105 reviews

Charming Home In A Historic Quiet Nashville Haven

This cozy chic 3 bedroom, 2-bath home, ideally located near the vibrant East Nashville neighborhood and, the iconic Grand Ol' Opry, with just a short 15-minute drive to downtown. Each carefully curated room ensures a restful night's sleep with cozy bedding and the promise of fresh morning coffee. The equipped kitchen invites you to indulge in culinary adventures or whip up a quick meal. Alternatively, relish moments of tranquility on the expansive 2-acre property, perfect for unwinding.

Guest favourite
A modern two-story home features a sleek dark exterior with large windows allowing natural light to fill the spaces. A wooden staircase leads to the front door, while a small garden with green shrubs and flowers enhances the entrance. The surrounding area is paved and offers ample space.
Home in Madison
4.93 out of 5 average rating, 110 reviews

Brand new - 10 mins from BroadWAY

Welcome to our brand new construction home, located just minutes away from the bustling downtown area and major highways. Our open floor plan is perfect for families and groups, with plenty of space to relax and unwind. The backyard is great for outdoor gatherings, and the end street location provides a peaceful and quiet atmosphere. Plus, with the woods across the street, you'll enjoy added privacy during your stay. Though we don’t mind you smoking outside please do not smoke inside.

Top guest favourite
The entrance of the Tudor home features a charming arched brick doorway framed by lush greenery and floral planters. A stone pathway leads to the door, flanked by manicured grass and shrubs, creating an inviting approach to the house.
Guest suite in Nashville
4.98 out of 5 average rating, 232 reviews

Charming two bedroom suite near the Grand Ole Opry

Beautiful Tudor home on one of the most unique streets in Nashville. The eclectic collection of homes on our street is something everyone notes. Most of us know each other well and our kids have grown up together. To this day, we celebrate milestones, holidays and memories together. Miami (Avenue) might not be Mayberry, but it's pretty close! We hope you'll join us! Just 2 miles to the Grand Ole Opry, 12 to downtown Nashville and 10 to the Nashville International Airport (BNA).

Top guest favourite
An inviting open-plan living space features a rich leather armchair and a sleek wood stove. Large windows frame views of the surrounding forest, with a dining area visible in the background. Natural wood accents and warm tones create a cozy atmosphere.
Cabin in Goodlettsville
4.94 out of 5 average rating, 530 reviews

Enjoy Nature at a Secluded Cabin near Nashville #2018038413

Made from reclaimed materials, this charming and newly constructed cabin has a vintage style that sits perfectly amongst the forest. It features a gorgeous open plan space and floor-to-ceiling windows that provide a 180-degree view of nature outside. Secluded on its own quiet 42 acres, the cabin lets you feel alone with nature. Further out, there's easy access to stores and restaurants with a few lovely places for antique shopping. Nashville itself is just a short drive away.

Top guest favourite
The exterior of a modern guest house is showcased, featuring a concrete facade and a wooden overhang. Large glass doors allow natural light to enter, while plants are placed on the steps and beside the entrance. A small seating area with outdoor furniture is visible.
Guest house in East Nashville
4.95 out of 5 average rating, 129 reviews

Riverside Homestead

Beautiful and newly built high end guest house right in East Nashville, TN. Studio space with fold down Murphy Bed and full bath. Includes full size refrigerator and amenities. Only 3 miles to Downtown or hot spots like 5 points East Nashville. Additionally, many local hot spots in walking distance such as Curry Boys BBQ, Ladybird Taco, Bite a Bit, and Sean Brocks latest pizza restaurant Sho. Off street parking provided with clear signage for guest parking. 1 car only.

Top guest favourite
A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.
Treehouse in Greenbrier
4.98 out of 5 average rating, 320 reviews

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, you are tucked away amidst the towering hardwoods--away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

Guest favourite
The living room features a mix of cozy seating options, including a patterned sofa and a dark armchair. A decorative area rug lies on the floor, complementing the modern decor. Shelves with framed art and a plant enhance the inviting atmosphere of the space.
Home in Madison
4.96 out of 5 average rating, 111 reviews

Cheerful, Fun, and Dog Friendly Home with Hot Tub

Located in the Madison neighborhood, you’re only a 10-15 minute drive away from downtown Nashville. Whether you’re looking for a place to call home while you explore and have fun in Nashville, or you’re just needing some rest and relaxation on a peaceful getaway, this cheerful and cozy home is the perfect place to stay. Local breweries, restaurants, and coffee shops are all nearby. Pet Friendly with pet fee of $50 per pet per stay. Brand new hot tub just added!

Top guest favourite
A private rooftop deck features a modern fire pit surrounded by comfortable seating. String lights hang above, creating a welcoming ambiance. A wall-mounted TV adds convenience, while the sky displays a colorful sunset, enhancing the outdoor space.
Home in Madison
4.99 out of 5 average rating, 150 reviews

10 min from Broadway Townhome with Rooftop+Firepit

Welcome to our centrally located townhouse in the heart of a peaceful neighborhood, just a short 10-15 minute drive away from the vibrant activities of Nashville! With keyless entry for your convenience, you can check in hassle free. Our townhouse is equipped with everything you need to make the most of your visit to Music City including; • Fully stocked and equipped kitchen • High speed wifi • Washer/Dryer • Private rooftop • Fireplace . Smart TVs

Guest favourite
An open-concept living area is presented, featuring a spacious gray sofa and a wooden coffee table. Four modern bar stools are positioned at a granite countertop separating the kitchen. Light streams through the large windows, complemented by light curtains, while a ceiling fan adds comfort.
Home in Madison
4.83 out of 5 average rating, 245 reviews

The Little Madison Home- All yours & dog friendly.

Welcome to our Little Madison Home! We invite you to enjoy your own private home. 1 mile from grocery, 5 minutes from East Nashville and a 15 minute drive from Downtown. Our home is perfect for a romantic getaway, family visits, business travelers, solo travelers and sightseers. Pup friendly with a fenced in front and backyard to make a happy getaway for you and your best dog pal. Our Little Madison Home is the warm hug of housing.

Popular amenities for Madison holiday rentals

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Avg. price$159 SGD$164 SGD$182 SGD$196 SGD$210 SGD$211 SGD$200 SGD$187 SGD$177 SGD$192 SGD$170 SGD$168 SGD
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Quick stats about holiday rentals in Madison

  • Total holiday rentals

    Explore 1,330 holiday rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 75,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    870 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Holiday rentals with a pool

    460 properties feature pools

  • Rentals with dedicated workspaces

    760 properties have a dedicated workspace

  • Wifi availability

    1,320 of Madison holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Madison rentals

  • 4.8 Average rating

    Madison stays are highly rated by guests – averaging 4.8 out of 5!

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