Holiday houses 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 & Spacious Land

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!

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.

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!

Stay Local - Game Room near Ampitheater / Baseball

Come and experience luxury and fun at our fully equipped airbnb! Our spacious 3BR 2BA property can comfortably accommodate up to 9 guests with its king, queen, bunk & trundle bed with memory foam mattresses. Immerse yourself in endless entertainment in our game room with a 4500 game arcade, foosball, air hockey, shuffleboard and more. The fully equipped kitchen and outdoor gas grill allow for convenient cooking and dining. Book now and make lasting memories with friends and family!

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.

Large Cozy 4 bedroom home sleeps 8 with pool

Welcome to The Haven Retreat—our cozy, remodeled home near I-220 and I-55. Enjoy nearby dining, shopping, and attractions. The pool can be seasonally heated upon request. Relax with all the comforts of home, and know we’re committed to making your stay enjoyable. Please note: no parties without approval, and no loud music or noise after 10 PM to respect our neighbors.

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.