Holiday rentals in Monroe County

4.94 out of 5 average rating, 333 reviews

Bungalow in Bloomington

Blue Lemon Bungalow - Quiet Getaway in Town!

Blue Lemon Bungalow is an adorable, newly renovated two bedroom in Bloomington with full living, dining, kitchen, and washer/dryer. In town with a country vibe. It has a huge yard with old growth trees, yet it is only a 5 minute ride to Downtown Court House Square or Indiana University Memorial Stadium. A large front porch with festive lighting gives you a place to enjoy the view. We have taken special care to make Blue Lemon Bungalow extra comfortable and stylish. Well behaved pets considered.

4.97 out of 5 average rating, 140 reviews

Pumpkin House. Chic downtown spotless fenced yard

Over 60 restaurants, bars, coffee shops, theater, comedy club, shops, health food grocery all in a very short walking distance. This is the perfect place for an active guest to experience boho Bloomington or attend IU events. Quality linens, SPOTLESS, uncluttered, new everything including beds,kitchenware etc. Designated parking for 2 and free street.Fast fiber 500Mbps speed internet and new Roku smart TV's. Third party booking allowed with approval from host and contact information of guests.

Guest suite in Bloomington

4.97 out of 5 average rating, 176 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, 252 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, 346 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, 120 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. ☺️

Guest suite in Bloomington

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.

4.99 out of 5 average rating, 173 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

Guest suite in Bloomington

4.95 out of 5 average rating, 1,290 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.

4.93 out of 5 average rating, 141 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, 197 reviews

Flat in Bloomington

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!

4.87 out of 5 average rating, 138 reviews

Great offer! Private entrance, Spacious, King-IU

Seasoned and experienced superhosts host this charming private suite with a private entrance. It has one bedroom with a king size bed. The house is on a very quiet street. You may not even know you're in the middle of town. You may see deer and other animals roaming around the neighborhood. The space includes private bathroom, kitchenette, and a sitting area with a loveseat and a small dining area.

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Popular amenities for Monroe County holiday rentals

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Other great holiday rentals in Monroe County

4.9 out of 5 average rating, 41 reviews

Cabin in Bloomington

Cheerful & Cozy Lower Cabin in Cohousing Community

AmberRating, 5 stars2 weeks ago

I received clear instructions that were helpful in finding the cabin and getting inside. We needed nothing after that, as the little cabin is well set up. It’s an adorable space, and even though it is nestled in between the YMCA and housing, it feels very private. It was warm and muggy during our stay, so we very much appreciated the dehumidifiers! Overall it was a very pleasant stay at the cabin while we visited family in Bloomington. Next time we’re in town, we want to rent the upstairs space just for a change of scenery!

4.96 out of 5 average rating, 73 reviews

The Landing Pad

DebbieRating, 5 stars4 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!

5 out of 5 average rating, 34 reviews

Cabin in Bloomington

The Town Cabin, built in 1840

ByranRating, 5 stars2 days ago

This is a must stay! The hosts are great and the cabin is perfect for getaways. We will definitely be staying again….soon.

Guest house in Bloomington

4.95 out of 5 average rating, 97 reviews

Private Cottage House One Mile from Downtown!

NicoleRating, 5 stars2 weeks ago

This was my second stay at Anna's and I felt right at home! I love how peaceful and quiet the area is while still being so close to everything downtown. Super comfortable, spotless space with comfy bed. Love being able to walk over to Soma's for coffee and take walks in the area parks etc. Thank you, Anna!

Superhost

Holiday home in Bloomington

4.81 out of 5 average rating, 53 reviews

Modern A-Frame

NicholsonRating, 5 stars4 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.

4.96 out of 5 average rating, 252 reviews

Cabin in Unionville

“Lemon Blossom”Lakehouse by Brownsmith Studios

KeithRating, 5 stars1 week ago

Jonah's cabin was absolutely beautiful it was as promised. the cabin had a woodsy rustic feel to it while being buried in the woods and yet it had a touch of class with the walk-in steam shower. everything about the place is fantastic. the open concept kitchen-living space was a perfect family environment.

5 out of 5 average rating, 67 reviews

Cottage in Bloomington

Cozy Cottage : easy + peaceful w/ private backyard

PeterRating, 5 stars1 week ago

Pristine cottage in a great location. Very clean, nicely updated, well appointed. Lisa and Harold were superb hosts.