Vacation rentals in Bolton

A set of wooden stairs with a polished finish leads up to the second floor. Soft gray walls enhance the natural light from a nearby window. Light fixtures hang from the ceiling, providing illumination along the staircase.

4.95 out of 5 average rating, 111 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!

4.97 out of 5 average rating, 155 reviews

A spacious living area is illuminated by natural light from large windows, showcasing views of a pool area. Comfortable seating arrangements include a sectional couch and armchairs, while a fireplace and wall-mounted television add to the space's functionality.

Apartment in Jackson

*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!

4.88 out of 5 average rating, 51 reviews

A comfortable sofa with several pillows is placed in a bright living area, accompanied by a rustic coffee table. Decorative items, including a small plant and a basket, adorn the table. Two framed prints with friendly messages are displayed on the wall behind the sofa.

Guest suite in Raymond

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!

4.99 out of 5 average rating, 119 reviews

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

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!

4.99 out of 5 average rating, 700 reviews

A lively concert scene is captured, featuring a stage illuminated with colorful lights and visual screens. The audience is visible in the foreground, surrounded by an energetic atmosphere, while performers are seen engaging with the crowd. The image exudes a sense of excitement and community.

Guesthouse in Brandon

The Cottage on College Street

The Cottage is very cozy with a mixture of vintage and industrial decor. Visitors will have complete privacy within the house at all times, but with our home close by, we are always happy to help should you need anything! We are located in Downton Brandon in the Historic District. The Cottage is a guest house seated behind our home; it is a very quiet place, and it is great for working individuals, couples seeking a fun concert experience, or families participating in ball tournaments.

5 out of 5 average rating, 47 reviews

A modern kitchen area features a central island with a marble countertop, surrounded by four wooden chairs. Stainless steel appliances, including a refrigerator and stove, are integrated into sleek gray cabinetry. Natural light streams through two large windows, highlighting the warm wooden flooring.

Loft in Bolton

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.

4.94 out of 5 average rating, 770 reviews

A unique side table features a whimsical design of a figure wearing a red jacket, supporting a glass top with both hands. The base displays intricate details and an artistic finish, blending charm and functionality in the cottage's decor.

Cottage in Jackson

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!

4.99 out of 5 average rating, 129 reviews

A serene lake scene displays smooth water reflecting the surrounding trees and autumn foliage. Bright blue skies contrast with vibrant colors from the changing leaves, creating a calming natural setting. The image captures the tranquility and beauty of the landscape.

Guesthouse in Jackson

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.

4.97 out of 5 average rating, 165 reviews

Home in Pearl

Modern Farmhouse w/ Gameroom + Close to Everything

Newly remodeled farmhouse in the perfect location. Fully stocked kitchen, on site laundry, outdoor gathering with fire pit. The game room has pool table, arcade games, karaoke machine, and extra large projector. Perfect location within 15 minutes of Downtown Jackson, outlet mall, Mississippi Braves, Brandon Amphitheater, golf courses, JAN airport, Tesla, several museums, & more. If you need a car, we can accommodate you through Turo. Just message us for availability.

Superhost

A bright kitchen features white cabinetry, a stove with four burners, and a microwave positioned above. The countertop provides ample workspace, with a sink under a window allowing natural light. Square floor tiles offer a classic touch, contributing to the cozy atmosphere.

4.78 out of 5 average rating, 110 reviews

Bohemian Bungalow side A

This is a home that we have split into two completely separate and private apartments. It is a cozy space in the heart of urban Jackson right behind Redeemer Church who loves on it so well. It’s only a few miles away from everything there is to do in Jackson and surrounding cities. The neighborhood is slowly but surely up and coming, where countless people love and invest into the community. Its not the prettiest neighborhood but we love it!

4.95 out of 5 average rating, 973 reviews

A charming porch area features a brick and gravel pathway leading to a whitewashed Tudor-style entrance. The porch is accented by a hanging light fixture and a table draped with a patterned cloth, surrounded by greenery and flowering plants.

Guest suite in Belhaven

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.

The swimming pool is framed by a spacious patio featuring comfortable seating options. Lush greenery surrounds the area, while a brick wall houses a chimney. Sunlight reflects off the water, providing a welcoming setting for relaxation.

4.87 out of 5 average rating, 103 reviews

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.

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Popular amenities for Bolton vacation rentals

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Other great vacation rentals in Bolton

A neatly arranged bathroom features a white sink with a polished faucet and a wooden mirror above. A modern toilet sits adjacent to it, while a small wire basket and toiletries are placed nearby on a wooden floor, enhancing the simplicity of the space.

Tiny home in Belhaven

4.73 out of 5 average rating, 453 reviews

The Ivy House- Tiny Home in Jackson

AriannaRating, 5 stars4 weeks ago

Beautiful space! Quiet and private location which I loved. Anna and William were very kind and helpful!

4.97 out of 5 average rating, 31 reviews

A serene pond reflects the surrounding trees, with a gentle fountain creating ripples on the water's surface. Two horses are seen walking along the grassy bank, accompanied by a person. Lush greenery enhances the peaceful country setting.

Cabin in Utica

Goodbye City Lights!

KenRating, 5 stars6 days ago

Just a bit off the main roads but not far enough to be an issue. Very quiet and serene. As good as anywhere I’ve ever stayed. Snacks were appreciated. The house is perfect. The yard is beautiful.

4.98 out of 5 average rating, 62 reviews

A charming guesthouse is positioned amidst natural surroundings, featuring a covered porch with white pillars. Lush grass frames the building, and tall trees provide shade. Clear skies and distant greenery contribute to a serene outdoor setting, perfect for relaxation.

Cottage in Bolton

The Guesthouse~Cozy cottage near Raymond

JenniferRating, 5 stars1 month ago

Leah’s place was just as advertised. Quiet, peaceful, and (more than) well stocked. Communication was great, and she made it feel like I was at my own home. Thank you, Leah, for a great weekend at your cottage!

Home in Raymond

4.84 out of 5 average rating, 49 reviews

The Moody General

GregRating, 5 stars1 month ago

The Moody General was a wonderful place! We stayed there for a wedding that was occurring at The Raymond Venue close by. It was a fantastic place. We will definitely stay there again if we are staying in Raymond! Highly recommend.

5 out of 5 average rating, 11 reviews

A welcoming porch features traditional wooden rocking chairs positioned on a light-colored floor. Decorative lanterns illuminate the space, while potted plants add a touch of greenery. This area offers a serene spot for relaxation and enjoying the outdoors.

Home in Raymond

The Porter 1830

CourtneyRating, 5 stars1 week ago

We really enjoyed Sherry’s home! We loved the character of the house and the modern amenities she included! This included fans in the bedrooms which is life or death for a Texan! 😊We will definitely stay here again!

4.99 out of 5 average rating, 105 reviews

Guesthouse in Vicksburg

Out of Africa

RaquelRating, 5 stars1 week ago

This is the second time we have stayed in this beautiful cabin. It is in the middle of the woods so the scenery is amazing. Super comfortable place and Kyle and his family are always friendly. They even left us fresh eggs from their own chickens! We will definitely stay here again!

5 out of 5 average rating, 19 reviews

A modern living area features a mounted flat-screen television above a sleek wooden media console with decorative items. A small workspace with a chair is positioned nearby. Light-colored walls and wood flooring create a spacious, airy ambiance, complementing the open layout towards the kitchen.

Apartment in Fondren

The Cozy Fondren Loft

TarahRating, 5 stars2 weeks ago

Macalah's place was perfect for our guests who needed more space than we had in our home. They felt at home and walked to several restaurants and bars in the area! It was a perfect fit!

A modern bathroom features a sleek black and white design with patterned tiles. A round mirror is mounted above a minimalist sink, accompanied by neatly arranged towels. Natural light filters through a window, illuminating the soaking tub and wooden accent shelf.