Guest house holiday rentals in Monroe County

Adorable 1-bedroom guest cottage w/ free parking

Our peaceful and historic 1851 farmhouse guest cottage is located on Bloomington's Eastside. Centrally located to both Indiana University central campus and IU Memorial Stadium for IU Move-In, Family Weekends, Music and Sporting Events - a 5 minute drive. A quick drive and you will be on Kirkwood Ave enjoying the great many restaurants and local shops. 15 minutes from the quaint town of Nashville, IN where you can enjoy the local fare and bars and visit the one of a kind shops by local artists.

Tiny guest house

This little granny flat is an inspiring, light-filled space with all of the basics, located in a friendly neighborhood, and literally steps away from the host house. With one bed (an American Leather pullout coach in a full queen size) and a full bathroom with shower upstairs, and kitchenette and living space downstairs, you'll have everything you need for a comfortable stay. We are located a few blocks from a coffee shop, and an easy one mile walk from downtown Bloomington. All are welcome!

Get away in the woods ! Fire pit, Game room

You will love this cozy private retreat a short drive away from bigger town amenities. Heading into Martinsville for some lunch (or candy!), checking out the beautiful landscape for some walking/hiking at Morgan-Monroe State Forest. Hunters Honey Farm 4.3 mi. Cedar Creek Winery, Brewery, Distillery 20 mi. Morgan Monroe State Forest 20 mi. Martinsville Candy Kitchen 15 mi. Art Sanctuary of Indiana 15 mi. TraderBakers Flea Market 15mi. sit by the fire pit and roast marshmallows, game room !!

French Country Guest House

Enjoy the beautiful sunsets with a view of the valley below. Our 500 sq. ft. newly remodeled guest house is nestled in the woods, only 5 miles from the IU stadium and 9 miles from Nashville in Brown County. We are conveniently located right off of route 46. If you let us know what event you are coming for we would be happy to leave you a custom box of cookies in your kitchenette. Enjoy the locally sourced handmade goat soap in your shower compliments of the goat farm down the road.

The Pond House at Deer Creek Farms/ Greencastle

10-minutes to DePauw and downtown Greencastle is an idyllic 1 bdrm/1 ba country cottage facing a stocked pond, surrounded by woods & farm fields. Living room has a queen sleeper sofa for extra guests, WiFi, TV, dining table/chairs, electric fireplace, kitchenette w/small fridge, coffee maker & microwave. Enjoy the grassy lawn, fire pit, fishing in pond, drinks on dock with Adirondack chairs and more. Families w/ young children please contact us before reserving to learn of safety concerns.

Private Cottage House One Mile from Downtown!

This guest suite is *one mile* from campus and downtown and located in a safe, quiet residential neighborhood! Here you will be walking distance to Kirkwood and steps away from a local coffee shop, restaurant, and 2 parks! The space is complete with ample natural lighting (+ custom blinds for privacy), premium features like heated floors, and privacy for guests to enjoy a quiet, relaxing stay steps away from Btown's best nestled into a quiet backyard (often with deer!). No idiots.

Treehouse Retreat With a View of National Forest

This quaint apartment home is about five miles east of Bloomington and the IU Campus on Hwy 446. The property borders Hoosier National Forest and adjoins 8 miles of hiking trails, with just a short trek to Lake Monroe and a mile to Paynetown SRA. The living room has a wall of windows that looks out over the woods. A bright and airy kitchen w/ all major appliances is off of the living room. An interesting bedroom with a dormer and a large bathroom/ laundry room complete the home.

5 Min IU, Pvt Parking, Full Kitchen, Fast WiFi

🏡 Private Guesthouse ⚡️2 Miles: IU, Stadiums, DT, Golf, Lake & More⚡️ Welcome to your cozy and thoughtfully appointed retreat! This 400 sq ft studio has a slanted ceiling; ideal for solo travelers, couples, & IU visitors. Guests love the calm vibe, spotless space & all the little extras that make it feel like home. Special Offer: Early/late check-in/check-out — $20 — Max 2-3 hours. ❤︎ Add to your wishlist by clicking the ❤︎ in the top-right corner!

Casita Azul

Charming Newly Renovated Guesthouse close to the Heart of Historic Downtown Franklin. Ideal for the solo traveler or a couple. Enjoy a thoughtfully designed space featuring: a brand-new full bathroom with modern finishes, a convenient mini-kitchenette stocked with essentials, and an open-concept main room/ sleeping area. Additional amenities include free on-site parking, easy self check-in and check-out, high-speed Wi-Fi, & Roku TV. Pet-friendly!

The Country Gathering - Sleeps 4 - Greenwood/Indy

5 YEARS AS SUPER HOST!!! The Country Gathering is in the upstairs of a Carriage House that was built on the property of a large home, located on the border of Greenwood/Bargersville in Johnson County, Indiana. The Carriage House has charm and character with a wooded backyard sitting on 4 acres. Sit or swing on the beautiful covered porch while you enjoy the view of the lake and fountain or feel free to walk around and enjoy the park-like setting.

Hidden Retreat on 30 Wooded Acres 5 Miles to Town

Unwind at our cozy retreat situated on 30 wooded acres, yet only 10 minutes from Bloomington. Evoking a rustic warmth with modern comforts, the house is lovingly decorated with all the amenities you could desire. Guests will be able to enjoy all that Bloomington has to offer, or if a quiet evening in is what you're after you can relax on the sun deck or cozy up by the fireplace.

Pine Tree Cottage

Pine Tree Cottage is a cozy spacious efficiency apartment located at Woodcrest Farm. Our farm is a great location for a relaxing getaway. Walking trails and a relaxing garden and garden house is available for our guests. Woodcrest Farm is close to Hoosier National Forest, Spring Mill State Park and the Milwaukee Walking Trail, all within less than 1/2 hour traveling distance.