Vacation rentals in Bolton

*Home away from home! Studio suite/peaceful farm

We have renovated from floor to ceiling! Our fresh, clean space is exactly what you need for any occasion - whether you need a break from the daily grind or you’re just passing through. We provide a warm, comfortable environment and top-tier hospitality to make you feel like a friend, not just a visitor. We’re located at the end of a quiet, friendly street just minutes from downtown Raymond. During your stay, you'll have access to our gorgeous land including a play set, farm animals, and more!

The Funky Monkey Cottage in Fondren!

The Funky Monkey is a 1bedroom 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!

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!

Highland Court Raymond, MS

Highland Court is located in the Historical District of Raymond, MS one block off the Town Square. Our place has two bedrooms, one bathroom, a cozy living room/kitchenette. From our space you can stroll up the hill to Raymonds very own wedding venue, The Raymond, or shop several unique mercantile stores. Wether you are looking for a place to get ready before or after a wedding, or a perfect small town get away right off the Natchez Trace, Highland Court is the place you will want to stay.

Locust Street Cottage

This special place is close to everything, making it easy to plan your visit. Built in 1830 and lovingly renovated for now, it’s a slice of Vicksburg’s past. The Old Courthouse museum is visible from the back courtyard and the historic downtown is just a short walk. There’s a brewery and several unique restaurants just a few blocks away in the downtown with fun shopping close by. Casinos and the National Military Park are just a short drive. Has a desk, if needed and internet provided.

The Modern Hideaway

Welcome to your unique private oasis, where modern minimalist decor meets serene tranquility. This thoughtfully designed space features open-concept living areas filled with natural light and stylish furnishings, ensuring a comfortable and chic retreat. Step outside to discover your own private backyard space, perfect for relaxing or entertaining. Experience a getaway that makes an ideal choice for those seeking both comfort and privacy. Unwind and recharge in a world of modern comfort!

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.

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.

Belhaven Guest Suite - Private

Cozy private guest suite in Belhaven home with vintage kitchenette, queen bed, full pullout sofa, Keurig, toaster oven, microwave, hotplate, oven, and fridge. Private entrance and space to a single-family home in a beautiful neighborhood. Nearby Belhaven University, Millsaps College, hospitals, and downtown. Ideal for solo travelers, couples, small families, or those traveling for work.

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.

Bohemian Bungalow at Belhaven

1930’s Wood framed cottage in lovely Historic Belhaven. Walk to the UM Medical Center, Belhaven and Milsaps University, Mississippi Baptist Hospital and many other close by parks and locales. Home is charming and cozy with wonderful lighting and a gas powered fireplace. Well stocked for your stay.

Pier Serenity

Pretend you are lost in a magical forest as you perch on a log or curl up in the swinging chair. Your home away from home awaits you. Kick back and relax in this calm, quiet, private, stylish space. Located on 300 acres, enjoy privacy and seclusion from everyday life.