Holiday rentals with outdoor seating in Greencastle

5 out of 5 average rating, 205 reviews

Cabin in Unionville

Summer Forest Reset: King Beds & Lake Lemon Marina

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, this custom log home balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

A dining area features a round wooden table surrounded by transparent chairs, complemented by plush white seat covers. A modern chandelier hangs from the ceiling, illuminating the space. The room showcases a combination of hardwood flooring and black accent walls, with large sliding glass doors leading outdoors.

4.98 out of 5 average rating, 102 reviews

Modern 4 Bed Home On Golf Course Close To Campus +

4 bedroom, 2 bath-master w/shower guest ba w/tub & shower ranch home w/ 5th hole of the golf course as your view & literally steps from patio! Minutes from campus, restaurants & shopping. Quiet established neighborhood. (1) King bdrm, (2) bdrms w/full bed and (1) office/bedroom w/fold down couch. -Blackout curtains -Wifi -Spacious family room w/smart 75 in TV -Close to everything Outdoor patio w/furniture to enjoy the golf course views. Depauw themed basement w/ sauna, pool & poker tables

A cozy bedroom features a dark wood bed with clean linens and two pillows. A lamp sits on a nightstand beside the bed. A window with dark curtains allows natural light to filter in, and framed art is displayed on the wall.

4.98 out of 5 average rating, 134 reviews

Castle 853 - We aim to be the cleanest!

Very Clean, stylish and up-to-date, Bedford Stone, single level home. Fully furnished, all linens, towels, cookware included. Coffee and snacks are there for your stay. We are a 3 minute drive to DePauw University, Crown Industrial Park, and the Historic Downtown full of Fine Dining, Craft Beer & Wine, Music. 300 feet from People's Pathway. Located in the heart of Covered Bridge country. 40 minutes from Indianapolis including the International Airport and the Indianapolis 500 raceway.

Guest house in Crawfordsville

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.

4.96 out of 5 average rating, 635 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.

4.98 out of 5 average rating, 165 reviews

An exterior view of the home is captured, featuring a light gray facade and metal roof. Colorful flowers and pumpkins decorate the landscaped garden, complemented by a bench positioned under a tree. Neatly arranged windows provide an inviting look to the property.

Home in Gosport

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

A dining area is featured with a dark wooden table surrounded by six chairs. Natural light enters through two windows, illuminating the space. The kitchen is visible in the background, fitted with white cabinetry and modern appliances.

4.89 out of 5 average rating, 112 reviews

Peaceful Ctry Home 1 ac. Wlk to 3FatLabs. 3BR 2BA

Peaceful country home near 3 Fat Labs and Depauw University. Situated on beautiful and quiet 1 acre lot with fire pit. Relax on the back deck and enjoy view, visit Oakalla covered bridge or hike at nearby Depauw nature trails. Home has en suite master with King bed and open floor plan. Kids room with bunk, toys and pack n play. Bathtub in 2nd bathroom. Enjoy large selection of DVDs and games for kids and adults. Satellite TV and internet. Washer/dryer. Only 3.5 miles to Depauw.

4.91 out of 5 average rating, 516 reviews

The living area features wooden walls and ceilings, complemented by large windows that allow natural light to illuminate the space. Two seating areas include a brown sofa adorned with cushions and a rust-colored recliner, alongside a coffee table. A dining area can be seen in the background.

Cabin in Martinsville

Grandpa's Cabin at Heidenreich Hollow

Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!.

4.79 out of 5 average rating, 142 reviews

The rustic barn is set against a vibrant sunrise sky, showcasing a mix of pink and orange hues. Lush green grass surrounds the barn, with farm equipment visible nearby. Trees and open fields fill the background, reflecting the charm of the rural landscape.

Barn in Rockville

The 1938 Barn

The 1938 Barn is located in the ❤ of Covered Bridge Country in Parke County. You will love the rustic charm of this converted hay barn built in 1938. Come relax by the camp fire or explore our many Covered Bridges and local State Parks. The farm also hosts Henry's Market, a market garden providing fresh meat and vegetables which makes summertime an excellent time to visit! Please note: There is NO WI-FI, NO CABLE. We have a selection of DVDs. Limited cell service, AT&T works best.

4.94 out of 5 average rating, 108 reviews

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

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.

4.94 out of 5 average rating, 232 reviews

A serene pool area is framed by lush greenery, highlighted by a sparkling pool with colorful floats. Cozy lounge chairs provide inviting seating around the pool, complemented by shaded gazebo spaces, ideal for relaxation. The scene reflects a tranquil outdoor retreat.

Home in Poland

Captain Bill's Guest House/seasonal swimming pool

Welcome to Captain Bill's Guest Lodge at Cagels Mill Lake! This gorgeous home offers modern amenities in a countryside setting. Perfect for bikers, boaters, fisherman, and anyone looking to enjoy lake life. Our guests are welcome to join us poolside at the main house. Our private pool is open only to us and our listed guests at our two Airbnb units. We're located seconds from the boat ramp and a short drive to Cataract Falls and Lieber State Park. Pool is seasonal.

4.93 out of 5 average rating, 373 reviews

A single-story home is displayed, featuring a light-colored exterior with a red metal roof. A spacious porch, equipped with seating, is visible at the front. Surrounding grass is neatly maintained, and trees provide natural shade nearby.

Home in Brazil

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

4.98 out of 5 average rating, 287 reviews

A single-story cabin is framed by lush greenery, showcasing natural wood siding and a welcoming front porch. The porch features seating arrangements and decorative elements, while the pathway leads to a gravel driveway, enhancing the serene ambiance of the surrounding woods.

Cabin in Carbon

Parke County Dream Cabin

Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!

Popular amenities for outdoor seating rentals in Greencastle

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.92 out of 5 average rating, 154 reviews

A charming home is framed by colorful shrubs and well-maintained landscaping. A concrete pathway leads to the front door, which is accented by a small welcome sign. The home's exterior features a combination of tan brick and orange siding under a gabled roof.

Home in Terre Haute

Cozy Cottage 3-bedroom in Southeast Terre Haute

4.92 out of 5 average rating, 135 reviews

A spacious living area features a comfortable sectional sofa, light-colored walls, and a ceiling fan. A wooden coffee table sits on a patterned rug, complemented by a side lamp. An office chair is visible near a small table, providing a functional workspace.

Home in Brownsburg

Brownsburg House

4.89 out of 5 average rating, 105 reviews

A spacious deck is seen, featuring a circular table with four cushioned chairs and a large umbrella providing shade. Surrounding greenery is visible, adding a natural backdrop to the outdoor space.

Home in Bloomington

House Around the Corner

The living area features a cozy seating arrangement with upholstered chairs and a plush couch. A large painting of an elephant adorns the wall above a wooden fireplace. Natural light fills the room through double windows that are framed by patterned curtains.

5 out of 5 average rating, 53 reviews

1860’s Art House

A spacious modern structure is set against a clear blue sky, featuring a hip roof and large windows that allow natural light to fill the interior. The exterior is accented by stone pillars and a wide porch, surrounded by a grassy field.

5 out of 5 average rating, 55 reviews

Quiet Country Retreat Near DePauw University

4.94 out of 5 average rating, 136 reviews

A tranquil fire pit area features six wooden chairs arranged in a circular layout around a stone fire ring. The setting is surrounded by lush greenery, with the soft glow of sunset visible in the background.

Home in Whitestown

Florence Cottage~Modern Country

4.84 out of 5 average rating, 125 reviews

The front view of the house showcases a classic white exterior with a welcoming entrance. Lush green shrubs frame the entrance, and a driveway leads to a detached garage seen in the distance. A clear blue sky complements the home's inviting appearance.

Home in Brownsburg

Cozy and Comfortable, great Fall destination!

A warmly appointed living area features a decorative fireplace framed by rich wooden accents. A round coffee table rests in the center, surrounded by comfortable seating. A staircase is visible in the background, adding architectural interest to the space.

5 out of 5 average rating, 63 reviews

Indulgence at DePauw

Apartment rentals with outdoor seating

4.65 out of 5 average rating, 20 reviews

A modern living room is highlighted by a colorful television display and stylish furnishings. A green armchair sits next to a white coffee table, complemented by plants and a floor lamp. Large windows with dark curtains open to a private balcony.

Flat in Whitestown

20 mins DT | Sleeps 9 |Verdant Retreat SpaciousGym

4.92 out of 5 average rating, 13 reviews

A lush green lawn is bordered by trees, providing a serene view of the lake in the distance. The sky is bright with scattered clouds, adding to the natural beauty of the surroundings.

Flat in Crawfordsville

Lake Treehouse

Flat in Bloomington

New place to stay

Modern Charming Condo

4.89 out of 5 average rating, 37 reviews

An open-plan living area features a comfortable leather sofa and a stylish round coffee table atop a patterned area rug. A modern armchair adds seating, while large windows allow natural light to fill the room. A ceiling fan and wall-mounted TV complete the space.

Flat in Zionsville

Zionsville Luxury Condo 1BR with Balcony

A well-lit sitting area features a dark sofa, a small table, and a floor lamp beside it. A patterned area rug adds warmth to the hardwood floor, while a bouquet of yellow flowers provides a cheerful accent on a dark surface.

Flat in Terre Haute

4.77 out of 5 average rating, 111 reviews

Large Suite in Collett Park

4.98 out of 5 average rating, 90 reviews

An outdoor fire pit area is framed by simple wooden seating, set within a gravel base. Surrounded by trees and open space, a staircase leads to the upper level of the house, while vehicles are parked nearby, creating a serene and accessible setting.

Flat in Ellettsville

8 miles From IU Stadium/Campus: Country & Quiet

4.93 out of 5 average rating, 89 reviews

A modern country home is shown, featuring a light blue exterior and a metal roof. Snow covers the ground and is lightly dusting the surrounding trees. Large windows fill the front, allowing natural light to enter the space. A welcoming front door is framed by minimalist decor.

Flat in Ellettsville

Secluded space with private deck

4.95 out of 5 average rating, 19 reviews

Flat in Rosedale

The Getaway2/ Sleeps 6/ hot tub & sauna! & more!

Other holiday rentals with outdoor seating

4.93 out of 5 average rating, 29 reviews

A spacious living room features a rounded gray sectional sofa facing a flat-screen TV on a wooden stand. Natural light enters through a window, with a view of greenery. A wall with rustic wood paneling adds texture, complemented by a clock and plants.

Guest house in Rockville

Raccoon Lake Retreat

4.92 out of 5 average rating, 64 reviews

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

Come Live The Barn Life In Town!

A two-story Victorian home is surrounded by a well-maintained garden featuring shrubs and landscaped plants. The exterior showcases a combination of green siding and a light gray roof, with large porch columns and dark window trims. A white picket fence enhances the property's charm.

5 out of 5 average rating, 10 reviews

The Trillium House at DePauw - 4/5 BR 3.5 BA

5 out of 5 average rating, 42 reviews

The studio features a combined living and sleeping area. A spacious bed is positioned near a wall with wooden cabinetry. A modern kitchen with stainless steel appliances is visible alongside comfortable seating arrangements. Warm wood tones and a well-lit environment create a welcoming atmosphere.

Loft in Greencastle

The Historic Boulders Circa 1910

5 out of 5 average rating, 12 reviews

A rustic log home is showcased with a stone chimney and a welcoming porch. The property features large windows, wood siding, and a spacious outdoor area, surrounded by lush greenery and landscaping, creating a serene and inviting environment.

Cabin in Greencastle

Cabin retreat

A historic farmhouse with a large wrap-around screened-in porch is set against a backdrop of autumn leaves. A gravel pathway leads to the main entrance, and several white Adirondack chairs are positioned on the lawn, inviting guests to relax and enjoy the surroundings.

5 out of 5 average rating, 32 reviews

Authentic Family Farmhouse on Pond / Greencastle

The exterior of the home is captured from above, featuring a red metal roof and a surrounding expansive lawn. Towering trees provide a natural boundary, and gravel pathways border the manicured yard, enhancing the serene setting.

4.98 out of 5 average rating, 49 reviews

Clean, functional and charming home

The exterior of the Victorian home is characterized by a multi-gabled roof and decorative accents. A spacious porch wraps around the front, adorned with patriotic bunting. A welcoming sign indicates the guest house, with manicured grass and landscaping enhancing the property.