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Holiday houses in Upland

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Top-rated holiday rentals in Upland

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

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Guest favourite
Home in Upland
4.99 out of 5 average rating, 256 reviews

Brick House Upland

Intentionally designed for short term stays, Brick House Upland is set to welcome you to Upland for your visit to Taylor University, Ivanhoes, Upland, or all that Grant County has to offer. With comfort a hotel cannot offer, we hope this welcoming space will allow you to relax and connect with your family and friends. Rates for most nights begin at $95 and increase for select and premium weekends. Use the search bar at the top of the page to start booking now. *Please note: Most weekends require a two night minimum

Top Guest favourite
The cabin features a rustic wooden exterior with a welcoming porch, complete with rockers for relaxation. Potted plants adorn the entrance, while a seasonal wreath enhances the welcoming ambiance. The steps are painted in a warm hue, leading to a charming door.
Place to stay in Peru
4.93 out of 5 average rating, 196 reviews

The Rustic Moose Cabin with hot tub on grounds

You won’t forget the peaceful surroundings of this rustic destination. We have many amenities including a hot tub and sauna on the premises. If you want peace and quiet this is the place for you! We have a nearby creek for kayaking and fishing, horses and a donkey to admire. Outdoor firepit for cooking and relaxing by. Indoor and outdoor games to play. WIFI and a smart TV for streaming. Private parking and a cabin next door for friends and family to stay at also! Check out our other 3 listings!

Top Guest favourite
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
4.93 out of 5 average rating, 186 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!

Top Guest favourite
The exterior of a historic brick building is displayed, featuring a prominent awning and colorful artwork in the windows. Decorative plants are arranged beneath the windows, adding a touch of charm. The building is set along a sidewalk, with neighboring structures visible.
Apartment in Fairmount
4.96 out of 5 average rating, 222 reviews

Enjoy Nostalgia In James Dean's Hometown

The Rebel Lodge is a fully restored historic brick building located in the heart of James Dean's hometown. lt is right across the street from the James Dean Museum, just around the corner from Main street, and only blocks from The James Dean Gallery. The building will sleep 4-5 with a comfy double bed, a pull out sofa and an additional sofa. It is decorated with fun mid century furniture and decor. Everything is freshly up to date with new furnace, & air conditioning. Please enjoy your stay!

Top Guest favourite
An open living area is presented with high ceilings and exposed beams. A comfortable gray sofa faces a wall-mounted television, while a dining table is positioned beside a fully equipped kitchen. Large windows allow natural light to illuminate the space, enhancing the inviting atmosphere.
Condo in New Castle
4.96 out of 5 average rating, 211 reviews

Maxwell-Commons #105, New Castle IN, 2bd2bth dwntn

#105 Maxwell-Commons: downtown LOFT for business, family, pleasure - HAVEN for peace. Wild party? PLEASE go elsewhere. Nea: HC Saddle Club; Go-Karts; NC High School; Hall of Fame. Indianapolis 50min; Richmond 30min; Muncie, Anderson 20min. Bring toiletries. Coffee available. THERE ARE STAIRS. 3 or 100s of guest voiced complaint re overnight trains. I am powerless over the midwest rail-schedules. It is fair to let would-be guests know. There are 2 assigned outdoor parking-spaces.

Guest favourite
A spacious living room includes a comfortable gray sofa adorned with patterned throw pillows. A round coffee table sits in the center, and a floor lamp adds light. Large windows with sheer curtains allow natural light to fill the space, complementing a cozy desk area.
Home in Marion
4.92 out of 5 average rating, 122 reviews

The Ranch on RaceStreet

Ranch on Race was recently renovated to best serve guests during their stay in Marion, IN. With comfortable furniture and stylish décor, it is the perfect place to unwind. Recharge in one of the two bedrooms, enjoy the spacious living room and kitchen, or be productive at the provided desk. Whether you are in town on business, catching a sporting event at IWU or visiting friends and family you will have everything you need to make your stay relaxing. Pack & play available upon request.

Guest favourite
The exterior of the small home showcases a charming design with white clapboard siding and intricate shingle patterns. Two symmetrical doors with glass panels are framed by tall windows, allowing natural light to illuminate the interior. A large concrete patio provides a welcoming entrance.
Home in Lagro
4.9 out of 5 average rating, 180 reviews

Riparian House -Rustic Setting on Wabash River.

Restored historic small home located on the banks of the Wabash River. Bike trail to the City of Wabash runs along rear of property. This cozy, 500 square foot one room house is perfect for your quiet getaway, the cyclist hitting the trail and roads, or putting your canoe or kayak in the Wabash River. A boat launch is 100 yards from property. Golf at Honeywell Golf Course and enjoy the benefits of our Bronze Membership. (Details in the online and onsite guidebook)

Top Guest favourite
A leather sofa is positioned in front of a wooden coffee table, adorned with accent pillows for comfort. A striking artwork featuring a Highland cow hangs on the wall above the sofa, flanked by modern lamps providing soft lighting. Natural light enters through two side windows.
Home in Marion
4.96 out of 5 average rating, 294 reviews

Lindsay's Landing: 3-Bedroom, 2-Bathroom Home

Welcome to Lindsay’s Landing — where comfort meets convenience. This stylish home is just steps from Indiana Wesleyan University, great dining, and shopping. Inside, you’ll find an open floor plan, a fully equipped kitchen, high-speed Wi-Fi, a smart TV, and comfortable beds with Giza cotton linens. Whether you're here for work, visiting family, or exploring the area, you'll feel right at home. Pets are welcome upon request for $12 per pet, per night.

Top Guest favourite
A fully stocked kitchen is visible, featuring white cabinetry and a stainless steel stove. Above the sink, a window allows natural light to illuminate the space. A coffee maker and additional appliances are present, along with a small black and white checkered rug on the floor.
Home in Upland
4.86 out of 5 average rating, 695 reviews

Cottage on 2nd NO Cleaning Fee Close to Taylor U.

No cleaning fees with your help! This is a quiet cottage getaway. Nestled in Upland, close to Taylor University, Indiana Wesleyan, and Ball State, this is a convenient location to have a relaxing stay. The cottage has two bedrooms, one bath, a fully stocked kitchen, and indoor/outdoor space to gather. You are welcome to enjoy a campfire in the yard or sit on the porch and enjoy the sunset. Come stay with us and enjoy all that Upland has to offer!

Top Guest favourite
A cozy living area features a comfortable gray sofa adorned with cushions and a light throw. A round wooden coffee table sits on a soft area rug, accompanied by a modern yellow chair. Natural light filters through the blinds, highlighting the space.
Home in Marion
4.95 out of 5 average rating, 247 reviews

Selby Street Suite

Walking distance to Indiana Wesleyan University, Wildcat Stadium, and more. If you’re in town for a campus visit, or to catch a sporting event at IWU, this is the place to be! Small home with many updates on a quiet, dead-end street. All the amenities to stay for a long period of time if necessary. Wi-fi, washer/dryer, full kitchen. Bed size is a QUEEN. Fold flat sofa included for additional guest.

Guest favourite
A two-story house with a stone chimney is surrounded by trees and a spacious lawn. A wooden deck extends from the upper floor, offering outdoor seating. The gravel driveway leads to the entry, providing access below to garage spaces. The clear blue sky complements the serene atmosphere.
Home in Indianapolis
4.92 out of 5 average rating, 135 reviews

White River Retreat

Escape to a private retreat on the White River in Indianapolis! This custom-built home offers a peaceful, open-concept space with a stone fireplace, pool table, and jetted tub. Enjoy 12 acres of shared grounds with river access, kayaks, and fire pits. Perfect for a unique getaway, feeling worlds away yet close to everything. Ideal for couples or small groups seeking tranquility and adventure.

Top Guest favourite
A cozy living room features a navy sofa adorned with patterned cushions. A light-colored armchair sits nearby, alongside two white ottomans on a textured rug. Natural light filters through sheer curtains covering the windows, highlighting the white dresser and decorative greenery.
Home in Marion
4.99 out of 5 average rating, 273 reviews

Caitlin's Cottage

Enjoy this cozy cottage in North Marion, close to grocery stores, restaurants, and easy access to Indiana Wesleyan University about 10 minutes away. Guests have access to the full house with an open floor plan and comfortable living space. High speed internet and the office make it convenient to work on the go, while the plush furniture and TVs to make it easy to relax and unwind.

Popular amenities for Upland holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Grant County
  5. Upland