Holiday rentals in Jamestown

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Top-rated holiday rentals in Jamestown

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Top guest favourite
A shaded porch area is visible, featuring several turquoise chairs arranged closely together along a concrete path. Lush greenery and blooming flowers frame the scene, offering a serene outdoor space conducive to relaxation.
Barn in Greencastle
4.92 out of 5 average rating, 65 reviews

Come Live The Barn Life In Town!

1 bed 1 bath unique red barn w/ sleeper couch + air mattress to accommodate up to 5 people! Experience the slow pace of the country life 3.6 miles from Depauw University. Imagine the peace & quiet from this location while roasting smore's in the chimenea from the front porch, but a quick 2.2 mile drive to all the restaurants and shopping! Features -Wifi -Washer/Dryer -Kitchenette -Coffee Bar -Walk In Shower (handicap accessible) -Air Mattress -Pull Out Sofa Bed -Walk In Closet -Keyless Entry

Top guest favourite
The entrance is accessed by a set of wooden stairs featuring a metal railing. A door with large windows is flanked by potted plants, providing a welcoming touch. Natural light filters through the greenery surrounding the entrance.
Guest suite in Indianapolis
4.99 out of 5 average rating, 104 reviews

A little secret hideaway

Keep it simple at this peaceful and centrally-located place. It’s close to everything, making it easy to plan your visit. It’s close to the airport, sporting events, and downtown. It’s up on the second level, but separate from the downstairs living. It has its own entrance and living space. 2.3 miles to Indianapolis airport 5.1 miles to Lucas Oil IRP 5.3 miles to Indianapolis Motor Speedway 8.3 miles to Lucas Oil Stadium 8.8 miles to Gainbridge Fieldhouse 8.8 miles to Indianapolis Downtown

Guest favourite
A wooden pathway leads from the cottage towards the water's edge, bordered by lush greenery. The peaceful lake is visible, framed by trees, creating a serene and natural setting. The pathway is designed with railings and is surrounded by grass and foliage.
Cabin in Monrovia
4.95 out of 5 average rating, 123 reviews

Waterfront getaway *cozy & peaceful*fishing*swings

Welcome to your peaceful lakeside getaway! This renovated boho-style cottage offers a quiet and laidback retreat. Featuring an open loft layout, a covered porch, and a large deck overlooking two small serene lakes, this home is designed for relaxation. Enjoy evenings under the Pergola with swings or gather around the hillside firepit for unforgettable nights. Its location also makes it easy for you to get around. You're just: 10 min to I-70 hwy 20 mins to the airport 30 mins to Indy Downtown

Guest favourite
Home in Brownsburg
4.86 out of 5 average rating, 22 reviews

Mid-Century Magic

Step into timeless style & comfort at this beautiful mid-century modern house. This single-level gem blends iconic 1950s design w/ contemporary touches to create the perfect getaway for couples, families, or remote workers seeking a peaceful escape. * 3 Bedrooms 2 Bathrooms Sleeps 6 * Cozy fireplace * Fully stocked modern kitchen * Large backyard & deck * WiFi smart TV Whether you're here to relax, attend a sporting event, or just soak in the vibes, this home offers a stay you won’t forget.

Top guest favourite
A charming exterior of the home is displayed, featuring a welcoming front porch with hanging planters. Lush green grass and colorful flower beds surround the property, while a paved path leads up to the entrance. A clear blue sky enhances the inviting appearance.
Home in Lizton
4.96 out of 5 average rating, 84 reviews

3 Bed + 2 Bath Family Home w/ Game Room

Welcome to our charming home in Lizton, IN! Just minutes from two stunning wedding venues and a short 30-minute drive to downtown Indianapolis, this recent remodel offers comfort and convenience. Enjoy a spacious, fully stocked kitchen with a coffee bar, a cozy living room with a fireplace and TV, a laundry room, and a lovely backyard seating area. With three bedrooms and two baths, our home comfortably accommodates eight guests. Perfect for wedding guests, families, or anyone visiting Indy!

Guest favourite
A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.
Farm stay in Thorntown
4.97 out of 5 average rating, 206 reviews

Heavenly Acres Farm and Learning Center

Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

Top guest favourite
A charming front porch is showcased, featuring two red chairs flanking a small table. Colorful flowers are planted along the walkway and in garden beds, adding vibrancy. The light blue exterior of the bungalow is complemented by bright white trim, creating an inviting entrance.
Bungalow in Speedway
4.96 out of 5 average rating, 160 reviews

Vintage Racer @ Speedway

Indy's Longest-Running Airbnb Superhost This AUTHENTIC 1940, 1,740' bungalow was beautifully restored in 2016 The downstairs with kitchen and full bath was remodeled in 2019 3 blocks/10 minute walk to the main gate of the Indianapolis Motor Speedway 3 blocks to Main Street and all of the restaurants, coffee shops, pubs The driveway fits 4-5 cars Off-street parking for 3 more vehicles Mere steps to the walking trail 10 miles to the Indianapolis International Airport 6 miles to downtown Indy

Guest favourite
The living area features exposed wooden beams and a large stone fireplace as the focal point. A leather sofa is positioned across from a wooden coffee table. A patterned rug adds color to the rustic space, complemented by a decorative armchair and soft lighting from nearby lamps.
Cabin in Indianapolis
4.94 out of 5 average rating, 132 reviews

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Welcome to our 150-year-old log cabin, nestled in the heart of Indianapolis! This cozy retreat offers a tranquil getaway while being just minutes away from all modern conveniences and only 20 minutes from downtown. Step inside and be greeted by the rich history of exposed wooden beams and a large stone fireplace. Our authentic rustic decor and cozy cabin amenities will transport you to a simpler time. Come experience the magic of Kit’s Cabin, where historic charm meets modern comfort.

Top guest favourite
The living area is furnished with a comfortable brown pull-out sofa and two chairs. A wooden coffee table sits in front, accompanied by a decorative area rug. Natural light enters through a window, with light curtains enhancing the cozy feel of the space.
Guest house in Crawfordsville
4.96 out of 5 average rating, 639 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Ten minutes to Shades State Park and twenty minutes to Turkey Run State Park. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College, 25 minutes to DePauw University, 45 minutes to Purdue. We live on site and our back door is approximately 600 ft. from from the Airbnb. At this time we do not allow pets. We clean the cottage in accordance with CDC guidelines.

Top guest favourite
The tiny home, set among lush greenery, features a green exterior with a welcoming porch. Seating areas are provided outside, surrounded by trees, offering a serene retreat. Soft sunlight filters through the leaves, illuminating the space.
Tiny home in Crawfordsville
4.99 out of 5 average rating, 147 reviews

Secluded farm tiny home near state parks

Welcome to your private setting on 60 acres with Christmas trees, woods, and excellent view of Sugar Creek from the back of the property! Connect with nature and solitude. Quiet setting in the trees; conveniently located near •Hiking (Turkey Run - 30 min; Shades State Park - 20 min), •Wabash College (5 min) and Purdue University (35 min), •Canoeing (public launch - 2 min ; Sugar Creek Canoe rental - 4 min). Groceries and dining are just 5 minutes away. Just under an hour to Indy.

Top guest favourite
A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.
Cabin in Bainbridge
4.94 out of 5 average rating, 112 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Superhost
Home in Advance
5 out of 5 average rating, 3 reviews

Cozy quiet and comfy home & garage

Enjoy this small-town place, cozy, quiet, & comfy with recent complete renovation. Convenient access to I-65 & I-74. We welcome long term guests if our calendar does not have your dates available, please reach out!! We may be able to accommodate :) All 3 bedrooms are appointed with blackout blinds, new beds, TVs and quality bedding. Big comfy couch. Heated tile bath. New Kitchen fully stocked; pots/pans, coffee maker & dishes. washer/dryer. 2 car garage.

Popular amenities for Jamestown holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Boone County
  5. Jamestown