Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern living area is furnished with a comfortable gray sofa and an accent chair. A large flat-screen TV is mounted on the wall, while a decorative rug enhances the space. Natural light enters through the windows, illuminating the open layout.
Home in Anderson
4.98 out of 5 average rating, 120 reviews

Smart Condo Near Harrah's Casino

Looking for a place to stay that's smart, convenient, and near all the action? Look no further than this Airbnb! This condo is the perfect spot for those who want to be close to the casino, shopping, and everything in between Indianapolis and Muncie. And with all the amenities of home, you'll feel comfortable and relaxed during your stay. So why settle for a boring hotel room when you can have a smart and stylish condo all to yourself? Book your stay today and experience the best of both worlds!

Guest favorite
An open-concept living space features a dining table set for four, with polished plates and glasses. A cozy sofa is adjacent to the fireplace, and the kitchen area includes wooden cabinetry and modern appliances. Natural light filters in through large windows, accentuating the wood paneling.
Home in Hartford City
4.92 out of 5 average rating, 218 reviews

Rustic Lake house with HOT TUB and Pool Table

Come relax in your cozy 1978 Lake House! Conveniently located between Muncie and Hartford City-16 min. from Taylor University, 24 min. from Ball State, 10 seconds from the dock! Enjoy the outdoors-Take out the kayaks, go fishing, enjoy the lake, soak up the sights in the hot tub, then end your night with a campfire! Inside-Shoot some pool on the 1800's pool table, pull out a board game with the family, or just relax in the four-season sunroom while watching the sunset. Enjoy Lake Time!

Guest favorite
The living area features a comfortable sofa and two wicker chairs, complemented by a coffee table on a soft area rug with leaf patterns. A Roku TV is positioned on a wooden console, while a decorative wall feature holds potted plants for a touch of nature.
Guest suite in Anderson
4.92 out of 5 average rating, 334 reviews

🦉Wooded Suite Retreat - 2BR Easy i69 Access!

Recharge surrounded by nature in this cozy, comfortable, clean 2 BR “in-law” suite nestled among towering ash trees in a rural, wooded neighborhood just outside town near the White River. Enjoy the full private apt (2 BR, LR, kitchen, bath, washer & dryer) on lower level of host’s home. Great for singles, couples, families or work travelers. Near I-69, Anderson University, Hoosier Park, Mounds State Park, Rangeline Nature Preserve, Anderson Airport, St Vincent & Community Hospitals & more!

Guest favorite
The dining area features a wooden table surrounded by six chairs, adorned with floral placemats. A potted plant sits at the center of the table. Natural light filters in through a window beside a decorative shelf, enhancing the welcoming setting.
Guesthouse in Muncie
4.87 out of 5 average rating, 373 reviews

Carriage House Loft Apartment

Welcome to our recently remodeled Carriage House Loft Apartment! We're happy to share our simple, comfortable, cozy space with you. Refurbished original hard wood floors with updated kitchenette area and bathroom. Charming and convenient, walk two blocks to the Cardinal Greenway & White River trails, and one mile to downtown Muncie! Perfect for 2 people, or a family with small children. Enjoy self-check-in, privacy, & dedicated parking steps from the entrance.

Top guest favorite
A spacious living area features warm wooden flooring and a cozy seating arrangement. A television is positioned on a dark wooden console, with a rocking chair nearby. A window seat with soft cushions offers additional seating, while framed photographs decorate the walls.
Apartment in Pendleton
4.98 out of 5 average rating, 357 reviews

Studio by Falls Park

Welcome to the Studio by Falls Park. This is a family-friendly studio apartment with a separate entrance. You are within walking distance to several good restaurants and the local drinking hole (The Wine Stable), Falls Park, walking trails. Located 10 minutes off I-69, and 20 minutes North of Indianapolis. Harrah’s casino is 15 minutes North on I-69. Studio has shower/bath, 1 queen bed, a full size futon, queen size blowup mattress and kitchen.

Top guest favorite
Guest suite in Anderson
4.86 out of 5 average rating, 64 reviews

Quiet Country Retreat Near Casino

Skip the noise. Stay somewhere peaceful. Private suite just 7 min from Harrah’s Casino & I-69, Mounds State Park, and Anderson University. Quiet, family-friendly retreat with easy private parking. Unwind in the cozy 1-bed suite: comfy bed, sofa sleeper, smart TV, and fast Wi-Fi. A mini-fridge, microwave, and coffee maker. Perfect for couples or small families seeking peaceful nights and quick casino fun.

Guest favorite
A modern living room displays a sectional leather sofa arranged around a circular coffee table. A sleek fireplace is built into the wall beneath a large flat-screen television. Subtle lighting fixtures illuminate the space, complemented by decorative plants and artwork.
Home in Anderson
4.83 out of 5 average rating, 18 reviews

Family-Friendly Retreat

Escape to this peaceful, family-friendly retreat—where cozy meets spacious in a serene, stylish setting. Perfect for families or small groups, this beautifully designed home offers comfort, charm, and plenty of room to relax. Enjoy quiet mornings, stylish interiors, and a welcoming vibe that feels just like home. Ideal for making memories, unwinding, and experiencing a true sense of calm.

Guest favorite
A sleeping area features a metal frame bed topped with soft gray bedding. Natural wood walls and ceiling enhance the cozy ambiance. A decorative area rug outlines the space, and light enters through two windows adorned with sheer drapes.
Home in Anderson
4.94 out of 5 average rating, 108 reviews

The Ravens' Nest

Located adjacent to Anderson University, this tiny home is big on charm and comfort. Across the street from Myers Hall, it is our hope that the home's convenient location, comfortable furnishing, and modern improvements will allow for an enjoyable visit. We live only 20 minutes away, and it is our aim to see that your stay in Anderson exceeds expectations.

Top guest favorite
A charming exterior view showcases a white brick structure with a spacious porch, flanked by lush greenery and colorful flowerbeds. Two sets of large windows provide natural light to the inviting entryway, framed by decorative plants and wrought iron fencing.
Home in Anderson
4.99 out of 5 average rating, 157 reviews

Historic Eighth Guest house

You'll have a great time at this comfortable place to stay. The unit is set up similar to a duplex . Shared stairway to upper unit with lockbox entry to unit . 2 bedrooms , 1 bathroom, kitchen, sunroom, family room, dining room, laundry room. Adults only in this unit due to balconies . Owner also currently hosts Historic Eighth carriage house .

Top guest favorite
A spacious living area showcases a wooden coffee table and a cozy chair, complemented by a soft throw. Arched doorways lead to a dining area featuring a table and chairs. Natural light enhances the warm wood flooring and neutral wall colors.
Home in Muncie
4.97 out of 5 average rating, 307 reviews

Cozy One Bedroom Bungalow

Forget your worries in this spacious and serene space. This one bedroom bungalow is very close to Downtown, Ball State University and IU Health Ball Memorial Hospital. One block from a beautiful walking/bicycle riverwalk. Only minutes from local restaurants , coffee shops and breweries. Washer and dryer on site.

Top guest favorite
A rustic lodge is presented with a gravel path leading to a covered front porch. Rocking chairs are placed along the porch, offering a view of the surrounding grassy area and trees. The building features a mix of wood and metal siding.
Farm stay in Middletown
5 out of 5 average rating, 17 reviews

Little Longhorn Lodge

The Little Longhorn Lodge! A rustic western themed stay at our small country farm. This home was designed with great attention to detail, hand picking every unique feature. You will feel right at home, relax and enjoy your stay. This is a working hobby farm so you will see horses and our friendly barn cats!

Top guest favorite
Home in Muncie
4.97 out of 5 average rating, 66 reviews

4 Bedroom Home - Hot Tub - Fire Pit

Welcome to your home away from home! This beautifully designed 4-bedroom, 2-bathroom house is perfect for families looking for comfort and convenience. Located in a quiet neighborhood, our home offers a peaceful retreat while being just minutes away from local parks, attractions, and dining options.

Popular amenities for Chesterfield vacation rentals