Vacation rentals in Bolton

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Top-rated vacation rentals in Bolton

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Top guest favorite

A welcoming home features a spacious front porch adorned with white railings and multiple gabled roofs. The driveway leads to a well-maintained yard with a combination of grass and decorative landscaping, providing a sense of openness. Ample parking spaces are visible for guest convenience.

Home in Jackson

4.95 out of 5 average rating, 117 reviews

Summer Dreams Corporate Executive Suites🍋

Summer Dreams is your home away from home. Beautiful enchanting home reserved to accommodate all of your vacation or business needs. Summer Dreams Executive Retreat is located off Hwy 80 W (No neighborhood) on Summer Drive. It is located minutes from Clinton, MS; Pearl, MS; I-55 & I-220 and the Natchez Trace. You will love that Summer Dreams Executive Suites is minutes away from the Outlet Mall of MS. Hospitals, Medical Clinics and Fire Stations are nearby. The entire house is yours to enjoy!

Top guest favorite

A spacious bedroom features a king-size bed with soft linens in calming shades. A stylish ceiling fan provides comfort, while a desk and chair sit ready for use. Natural light filters through window treatments, creating a relaxing atmosphere.

Apartment in Jackson

4.97 out of 5 average rating, 172 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!

Top guest favorite

A welcoming front porch features two comfortable wicker chairs with soft cushions, positioned beside lush greenery and blooming flowers. Natural light filters through the surroundings, highlighting the inviting atmosphere for relaxation and enjoyment.

Guesthouse in Raymond

4.99 out of 5 average rating, 122 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!

Top guest favorite

An open living space showcases polished hardwood floors and high ceilings with exposed beams. A modern kitchen island with seating is visible, alongside a comfortable seating area with a leather sofa. Soft lighting fixtures complement the overall design, creating a bright and airy atmosphere.

Loft in Bolton

5 out of 5 average rating, 49 reviews

The Bolton Loft 1

The Bolton Lodge is a one of a kind property. Built in 1892, it was used as a masonic lodge until its renovation in 2023. Enjoy the privacy and character of a small town with all the amenities you would expect in any modern home: full kitchen, Internet, smart TV, washer, dryer, and a walk-in shower. Located above Gaddis and Mclaurin Mercantile, you’ll be able to walk to B-town Steakhouse and S & S Burgers. Close to Interstate 20, old highway 80, the Natchez Trace, and Civil War Sites.

Guest favorite

Bright orange and teal decor defines a cozy living space, featuring a large monkey painting above a stylish bar with orange stools. A vibrant rug adds warmth, while a glimpse of a fully equipped kitchen with a retro-style fridge can be seen in the background.

Cottage in Jackson

4.94 out of 5 average rating, 797 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, movie theatre 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!

Superhost

A cozy studio space features a queen bed with crisp white linens, set against a backdrop of wooden beams and metallic roofing. A comfortable sofa with yellow accent pillows is positioned nearby, alongside a coffee table and a small bookshelf, providing a welcoming living area.

Tiny home in Belhaven

4.73 out of 5 average rating, 473 reviews

The Ivy House- Tiny Home in Jackson

Stay in this cozy Tiny Home! Only minutes from the Belhaven Town Center, some of the state's best restaurants, parks, and Museums, Downtown Jackson, and the famous Fondren area. Enjoy a cozy stay in the heart of the Historic Belhaven Neighborhood! The Ivy House is a fully furnished guest house with a kitchen, porch, bathroom, private entrance, and loft! Feel free to ask if you need anything during your stay or any recommendations of our favorite local attractions and restaurants!

Top guest favorite

The exterior of the Falk House features a mid-century modern design with a prominent overhang supported by slender columns. Lush green grass and tall trees frame the structure, creating a serene connection to nature. Expansive windows invite natural light into the space.

Guesthouse in Jackson

4.99 out of 5 average rating, 137 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.

Top guest favorite

A blue duplex is positioned under trees and framed by blooming flowers. The well-maintained front yard features a concrete driveway leading to the entrance. A garage is visible on the left, while a line of greenery borders the driveway.

Apartment in Belhaven

4.99 out of 5 average rating, 434 reviews

Downtown Apartment, Close to the Best of Jackson

Long-term discounts now available. Welcome to this cozy one-bedroom apartment in a quiet, safe neighborhood minutes from the heart of downtown, Belhaven university, and Millsaps. This well-lit space is part of a 1940s duplex with off-street parking and a private yard for outdoor relaxation after a long day-- perfect for business professionals and cultural enthusiasts. By default we do not allow pets, however we are open to it so please request and give details.

Guest favorite

An outdoor sitting area features several metal chairs and a coffee table on a grassy patch. The backdrop includes a gray and wooden structure, with plants adorning the walls. Natural light brightens the space, and a pleasant sky is visible above.

Apartment in Jackson

4.97 out of 5 average rating, 393 reviews

Secret Sanctuary in Fondren

This hidden private apartment behind my home is perfect for the traveling business person or the vacationers looking for a central location in the Fondren District. With off street parking, well away from any busy thoroughfare, you can be sure to enjoy peace and comfort. You will be inspired by the original decor and outdoor porch to go out and discover Jackson or rest and enjoy solitude. Also, there is a Purified Drinking Water Faucet installed in the apartment!

Superhost

A spacious covered outdoor deck features wooden beams overhead and ample seating. Two rocking chairs with patterned cushions sit on a warm wooden floor, alongside a cozy area rug. A potted plant adds a touch of greenery, complementing the scenic view of the communal patio.

Apartment in Belhaven

4.76 out of 5 average rating, 121 reviews

Homey 1 BR unit across from Belhaven Town Center

Built in 1925 and located in the historic Belhaven neighborhood, this vintage-style 1 bedroom apartment is centrally located near downtown Jackson and the Fondren art district. Explore this scenic area, from its unique, historic homes to a medley of locally-owned restaurants. Located across the street from Belhaven Town Center, have a delicious dinner at Elvie's Bistro, unwind with a drink at the Fertile Ground Beer Company, or grab a coffee at District Donuts.

Superhost

A hallway is framed by an ornate golden chair and a slender plant, leading to a blue accent chair positioned against a dark wall. Light reflects off the polished hardwood floor, creating a welcoming entrance to the suite.

Guest suite in Belhaven

4.95 out of 5 average rating, 1,003 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

A navy blue front door features an oval window with intricate glass detailing. A small wall-mounted light illuminates the entryway, while a charming sign reading "This Must Be the Place" is hung beside the door. A welcome mat is placed at the entrance.

Guesthouse in Raymond

4.94 out of 5 average rating, 332 reviews

Hope's Treasure

Hope's Treasure is just that--a sweet retreat less than 15 minutes from Mississippi College and Hinds Community College. With 2 bedrooms, a private bathroom, a comfortable living room, and a kitchenette, you can relax and enjoy some beautiful sunsets in a peaceful wooded setting. A picturesque half-mile drive leads from the gated entrance to your getaway.