Vacation rentals in Bolton

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.

Cozy Studio Suite on Spacious Land & Farm

Located at the end of a quiet, friendly, safe street just minutes from downtown Raymond, this guest suite is everything you need to take a breath while on your travels This space is newly renovated with all the amenities you could want - and more! We provide a warm, comfortable environment and top-tier hospitality to make sure you don't just feel like a visitor, but a friend. During your stay, you'll have access to our 6 acres of gorgeous land including a pond, play set, hammock, and more!

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!

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 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!

Walden@Raymond

Walden@Raymond is a small cabin with a private, personal-use salt pool that blends modern comforts with outside nature and beauty. This is an ideal place for quiet and reflection. Enjoy morning coffee watching blue heron on the lake or bake with a view of the fruit trees. In the summer, enjoy the pool at mid-day or a private night swim under a star-filled sky. In the winter, snuggle up in front of a wood burning fire with hot tea and a good book. This is the retreat you deserve. Enjoy!

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.

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.

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.

La Boheme Cottage # 3

This cottage is located in the Garden District of Vicksburg on the grounds of the Historic Home Flowerree. It should be fully equipped is everything you need hot water, air-conditioning, towels, and even the laundry room available. It has a charming ambiance and design. We have private off street parking. The Cottage is located a short distance from dining, shopping, galleries and museums.

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.