Holiday rentals in Monroe County

4.97 out of 5 average rating, 174 reviews

Hideaway Hollow - A Woodsy Getaway

Hideaway Hollow is a cozy, private guest suite in Bloomington, Indiana. Located on the north side, it is just fifteen minutes from the heart of downtown Bloomington, IU stadium, and an hour from Indianapolis. Nestled in the forest, the suite offers a covered porch with a private entrance, a spacious living room, a kitchenette, and a master bedroom with a full bath. Suitable for up to four guests, come to enjoy the serenity of country living, the comforts of home, and easy access to the city.

4.97 out of 5 average rating, 250 reviews

Cottage in Bloomington

Relaxing Retreat in the Woods

Relaxing retreat on 16 acres of woods , minutes from shopping, restaurants, Lake Monroe and the I.U. stadium--a 13 minute drive for basketball and football fans. Fire pit, grill, hammock, board games, kitchenette, CD, record player. No cable /television. Cell phone service and internet available if sometimes a bit spotty. The studio is in the woods so you may see or encounter wildlife including deer, opossums, raccoons, snakes, bobcats, coyotes and birds. Owner lives on property.

Guest house in Bloomington

4.95 out of 5 average rating, 340 reviews

5 Mins IU • Priv Parking • Fast WiFi • Cozy

🏡 Private Guesthouse ⚡️2 Miles: IU, Stadiums, DT, Golf, Lake & More⚡️ Welcome to your cozy, peaceful & thoughtfully appointed retreat! This 400 sq ft studio has a slanted ceiling; ideal for solo travelers, couples, remote workers & 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/out — $20 ❤︎ Add to your wishlist by clicking the ❤︎ in the top-right corner! ❤︎ Message me with any questions! ❤︎

4.98 out of 5 average rating, 118 reviews

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. ☺️

4.99 out of 5 average rating, 129 reviews

Campus-Side Retreat in the Woods

Across the street and literally walking distance from IU's sports facilities but surrounded by trees, this wooded retreat is a short drive or bike to downtown Bloomington's vibrant nightlife and community activities. This brand new, chique, and modern studio apartment boasts a skylit bathroom, a full kitchen with custom-made cabinets, washer/dryer on site, and professional decorating. In addition, we're a short drive, or slightly longer hike to Griffy Lake and only minutes from I69.

4.84 out of 5 average rating, 601 reviews

Lower Level Suite/Apartment, GREAT LOCATION!

LONG TERM STAYS WELCOMED DISCOUNTED! 1 bedroom, 1 bath studio with 2 BEDS and kitchenette (no oven). Wifi, refrigerator, coffee, space completely to yourself. Easy access to IU campus, downtown, shopping, golf, bus, and entertainment within 1 mile. Pets welcome, no cats! We do have 2 well behaved pups upstairs. They are in a separate unit completely. You won’t see them unless we are outside at same time Add my listings to your wishlist by clicking the ❤️ in upper right corner

4.99 out of 5 average rating, 172 reviews

Cabin in Unionville

Summer Forest Sanctuary: Adventure & Relaxation

Escape to "Cabin Porch Paradise," nestled on 40 acres of lush forest near Lake Lemon and just a short drive from charming Nashville, IN. This summer, ignite your romance or gather your closest friends for an unforgettable getaway filled with adventure, relaxation, and starlit nights. Romantic King Bedroom Cozy Queen Bedroom Unique Sleeping Porch Area Two Spacious Porches BBQ Shack Fire Pit Hot Tub Coffee Bar Board Games Washer & Dryer Boat Rental at Lake Lemon-10% discount

4.95 out of 5 average rating, 1,285 reviews

Strawbale Bungalow. Bloomington Indiana USA.

Art and book filled. Located in Bloomington Indiana. My 1920s bungalow includes two guest bedrooms with queen sized beds, down comforters, feather/down pillows, line curtains and private bathroom. The guest area also includes a garden porch, private entrance, living room and, dining area with microwave, small refrigerator and handmade maple table. NO KITCHEN. The bathroom is between the bedrooms and includes a Toto washlet bidet and EO toiletries.

Guest house in Bloomington

4.89 out of 5 average rating, 139 reviews

Studio by Kirkwood Ave close to I.U. and Downtown

Nice studio apartment in a quiet neighborhood right off Kirkwood Ave. Kirkwood Avenue is the heartbeat of the city of Bloomington and Indiana University. There is private entry with access to a lockbox for self check in. One queen size mattress and a futon is available. Full kitchen with refrigerator, microwave, oven and dishwasher. Television with a Roku which can mirror your phone. Please allow me to host your next stay in Southern Indiana.

4.93 out of 5 average rating, 139 reviews

Private entrance, cozy lower level pad

Private entrance to a lower level living area, queen size bed and bathroom. Living Area includes a breakfast table, refrigerator, microwave, Keurig coffee maker, coffee, electric tea kettle, tea, sweetener and creamer. Bedroom includes a closet and chest of drawers. Enjoy free wi-fi and a space completely to yourself. Come and go as you please! We are 2 miles from IU campus, downtown, shopping, and entertainment. We welcome everyone!

4.95 out of 5 average rating, 196 reviews

Spacious Country Apartment

Beautiful 2,000 sq ft apartment large enough to spread out and enjoy yourselves! Only 6 minutes from Sam's Club/Walmart/Starbucks. Perfect home base for IU or Lake Monroe. Abt 15 mins to IU Memorial Stadium/Assembly Hall & 20 mins to Fairfax boat ramp. Spacious parking. Country setting on lower level with private door/walkway. Beautiful yard and gardens. Fiber optic Eero mesh WiFi. Washer/dryer in unit. Free Tesla Charger. Comfy!

4.97 out of 5 average rating, 709 reviews

Vintage Bones, Modern Heart

Second floor studio apartment in two story home in the heart of Bloomington. Space is entirely self-sufficient with private entrance. Three blocks from Bryan Park, this peaceful neighborhood of Elm Heights is within short walking distance of downtown and campus. Pets are welcome, but there is a pet fee.

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Popular amenities for Monroe County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Monroe County

4.96 out of 5 average rating, 73 reviews

The Landing Pad

DebbieRating, 5 stars2 weeks ago

Comfortable spacious home right on the regional airport property. Home was exactly as described on listing. It was unique, enjoyable, and close to shops & restaurants. About 15 mins from IU, but we didn’t need to be near the campus. The house was plenty big for us to spread out and enjoy the big TV. The pots and pans in the kitchen were very handy, but when shopping, be sure to buy basics like cooking oil, salt/pepper, & coffee. A dishwasher would’ve been handy, but to avoid washing, we just brought paper plates and cups. We eat a lot! The shower water had great water pressure and got comfortably hot. Lots of towels and linens too. We appreciated the blackout blinds in the bedrooms as it got quite sunny early in the mornings. Beds were comfy too I like a little reading lamp at my bedside, but there was only one lamp like that in the sitting room. I took it with me to the bedroom every night just so I can read & turn it off easily. Kristine was responsive & helpful. Great stay!

4.98 out of 5 average rating, 64 reviews

Cozy getaway w/close proximity

BethRating, 5 stars2 weeks ago

We really enjoyed our stay. His place was close to Bloomington and perfect for our weekend. His home was extremely clean and exactly as described. We would definitely stay with him again on our next trip to the area.

4.97 out of 5 average rating, 29 reviews

Crimson Maple; King bed; Near IU Stadiums

ElizabethRating, 5 stars1 week ago

This was a great stay in Bloomington—would stay again!

5 out of 5 average rating, 51 reviews

Walk-out Guest Suite/Apartment near IU

ShaliniRating, 5 stars4 weeks ago

Had a lovely stay, Erin went all out to make us comfortable. Would highly recommend the place for a peaceful quute stay.

Guest house in Bloomington

4.95 out of 5 average rating, 96 reviews

Private Cottage House One Mile from Downtown!

MaryRating, 5 stars1 month ago

Anna’s place was perfect for our short stay visiting IU. It was clean, quiet, and the bed and air mattress were both very comfortable. It was a cold weekend, so we really appreciated the heated tile floor in the bathroom!

5 out of 5 average rating, 58 reviews

Little House on the Corner

AmyRating, 5 starstoday

The little house on the corner was perfect for our extended weekend away. Maureen has thought of every need that a traveler would need and even supplies if something was forgotten. I love the yard with the storm drain. It was like a little creek. We truly enjoyed our time there.

Superhost

Holiday home in Bloomington

4.88 out of 5 average rating, 51 reviews

Modern A-Frame

NicholsonRating, 5 stars3 months ago

Has a private valentines getaway and it was perfect! The house is very cute and looks even better than the photos! It snowed while we were there and it looked amazing. Restaurants are about 10-20 minutes away so plan accordingly. We went to Kimu and it was delicious. The home is very cozy and perfect for 2-4 people.