Holiday houses in Chesterfield

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Top-rated holiday rentals in Chesterfield

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

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Top Guest favourite
A cozy sleeping area features a queen-sized bed dressed in a decorative quilt with accent pillows. A floral painting adorns the wall above the bed, while a bedside lamp provides soft lighting. Drapes frame the window, allowing natural light to filter in.
Guest suite in Greenfield
4.95 out of 5 average rating, 283 reviews

Greenfield German Cottage-minutes to downtown Indy

The perfect place for you to stay when visiting Greenfield or nearby Indianapolis. Located within 1/2 mile of I-70. Restaurants and shopping within 1 mile. Downtown Indy is an easy 20-mile drive. We offer a comfy queen size bed, comfy roll away twin bed, kitchenette, full bathroom, walk-in closet, sitting area with couch and tv, private entrance with a private drive and parking area. You can also enjoy many extra features on the property, which include beautiful flower gardens and fountains.

Top Guest favourite
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, 112 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!

Top Guest favourite
A serene bedroom features a spacious bed with soft linens and decorative pillows. A reading chair is positioned next to large windows, allowing natural light to illuminate the room. A decorative sign and plants add subtle character to the calming atmosphere.
Guest suite in Muncie
4.97 out of 5 average rating, 445 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Top Guest favourite
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, 330 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 favourite
A white, single-story house is shown with a sloped roof and a welcoming front porch. Two red chairs are positioned on the porch, inviting relaxation. A concrete walkway leads from the street to the entrance, bordered by neatly kept grass and shrubs on either side.
Home in Muncie
4.89 out of 5 average rating, 66 reviews

A Dandy Duplex - BSU & Hospital

Whatever brings you to Muncie – visiting Ball State University or IU Health/Ball Hospital, wish to explore downtown Muncie, have a good time and enjoy shopping and great restaurants, business or any other reason, the location of this place and the way it is suited makes your perfect choice! Enjoy your stay in this cozy, newly remodeled space! located just a few blocks south of BSU campus and minutes from the hospital it is also a short 5 minute commute to downtown.

Superhost
Cabin in Chesterfield
4.86 out of 5 average rating, 7 reviews

Muncie Cabin 2

ADA. Sleeps 4, 1Queen bed, 1 sleeper sofa queen size, Linens are included, full Bathroom including towels, kitchen with some utensils, full refrigerator and microwave, dinette table sits 4, heating and air conditioning, patio furniture, fire ring, and grill with filled propane to cook. 4 plates, 4 coffee cups, 1 coffee pot, 4 bowls, Pitcher w/ 4 cups, 2 blankets, 4 sheets, 4 pillows, 4 towels set (each set is 1 towel, 1 wash rag and 1 hand towel)

Top Guest favourite
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, 350 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.

Guest favourite
A spacious yard is framed by lush green grass under a colorful sky at sunset. Trees provide shade, while a vast field stretches into the distance, contributing to the peaceful ambiance of the serene surroundings.
Guest suite in Anderson
4.82 out of 5 average rating, 51 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 favourite
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
4.82 out of 5 average rating, 17 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.

Top Guest favourite
The exterior of a carriage style guest house is displayed against a clear blue sky. The property is set on expansive green grass surrounded by mature trees, showcasing autumn foliage. Rolling hills can be seen in the background, adding to the serene country setting.
Guesthouse in Yorktown
4.97 out of 5 average rating, 38 reviews

Hickory Hill Estates Carriage House (Muncie)

Muncie Area near I69- Beautiful and spacious carriage style guest house sitting on a park like country setting. Located on 8 acres, surrounded by shag bark hickory trees, rolling hills, a pond, and neighboring cattle, this space is guaranteed to provide a peaceful stay and privacy. Conveniently located just 2.5 miles from I69 and a 12 minute drive from Ball State.

Top Guest favourite
A spacious studio features a comfortable bed with a light-colored headboard, accompanied by a cozy seating area with a chair and couch. Natural light illuminates the room, and a decorative rug is placed on the floor. Wall-mounted lamps provide additional lighting.
Home in Pendleton
4.95 out of 5 average rating, 346 reviews

Studio M

Studio M is located in the small Historic town of Pendleton, IN. The home is within walking distance of our shops, restaurants and Falls Park. We have a fully stocked kitchen, car port with chairs to sit out and enjoy the beautiful outdoors. Our house is conveniently located to Fishers, Anderson, Noblesville and Indianapolis.

Top Guest favourite
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, 299 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.

Popular amenities for Chesterfield holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Madison County
  5. Chesterfield