
Places to stay near Oliver Winery
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Top-rated holiday rentals near Oliver Winery
Guests agree: these stays are highly rated for location, cleanliness and more.

“Lemon Blossom”Lakehouse by Brownsmith Studios
This home is a dream come true for me building it from the ground up. Bring your boat. No Partiers this home is being offered to families and couples who won’t disturb my neighbors or our peaceful cove. The home features a steam shower, king bed, reclining sofa, dock, kayaks,reading/social nook at signature windows over the creek/lake. The deck floats in the forest with abundant wildlife all around. premium WiFi . 15min to Bloomington. 20min to Nashville/Brown County St. Park. Newly paved lane

Elevated Wilderness | Mindful Retreat | 2 Kings
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, Cabin Porch Paradise 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.

Brown Co Getaway: Sleeps 10-Hot Tub-Firepit-Grill
Enjoy a stay of charm and heritage at a 1906 Brown County home known as Helmsburg Station. It was originally owned by the Helm's of Helmsburg, IN and has been completely renovated from the exterior walls inward during 2019. Helmsburg Station pays tribute to the history of its quaint location as the original direct route from Indianapolis to Brown County via the railroad line. From Helmsburg, the rest of the route to Nashville was by horse and wagon or by foot. Check out our new drone photos!

Beautiful 2 bedroom Rental Unit in Martinsville
This is a newly designed rental for you and your family in mind. Just pack your bags and come and stay a while. You can enjoy all that central Indiana has to offer. It is close to everything you can imagine. This Rental is in the heart of Martinsville cultural district but 20 mins south to Bloomington IU stadium and 30 mins to Indianapolis Lucas Oil stadium. We have it all from sports venues, shopping, Dining and beautiful parks to hike and just have a great time exploring central Indiana.

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. ☺️

There's No Place Like Dome!
Come enjoy fabulous Bloomington, IN from your own private paradise! The 1400 square-foot renovated dome home boasts panoramic wooded views and sits on 6 acres of a secluded, park-like setting only 17 min. from downtown. The dome sleeps 4 guests with an open, divided, (not fully private) loft with one full bed and one queen bed. There is one full bath, dining for six, island seating and a fully equipped kitchen. It also features a fireplace, laundry facilities and front and back decks.

Cozy Cabin Close to University 1
The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

Kingsley House Near IU/Stadium
Have fun with the whole family at this stylish open concept place. 3 bedroom 1300sqft house with one KING BED, 1 queen, and 1 full. TVs in ALL bedrooms. Enjoy access to laundry, fast wifi, and fully fenced in back yard! Located in one of the best locations close to the stadium, golf courses, shopping, great trails/parks, and much more. Dog friendly (NO CATS) We do offer early/late check in/out for $20. Add my listings to your wishlist by clicking the ❤️ in the upper right corner.

Nice Downtown Condo
Nice downtown condo. It is right on the B-Line trail and is walking distance to downtown and campus. The unit is an upstairs corner condo. For longer stays, there is an occupancy limit of only two unrelated adults allowed by our HOA. NO PARTIES OR PETS. Netflix, Prime Video, Disney Plus, and Vizio free channels, you can access them from the Home Screen. There is street parking between 2nd and 3rd street, in addition to the dedicated space and marked guest parking on Madison street.

Hideaway Hollow - A Woodsy Getaway
Hideaway Hollow is a cozy, private guest suite attached to the owner's home. An old-school Airbnb experience, we offer a home away from home inside ours. Located on the north side of Bloomington, it is just 15 minutes from downtown Bloomington, the IU stadium, and an hour from Indianapolis. Nestled in the forests of the Indiana Uplands, the space offers a covered porch with a private entrance, a spacious living room, a kitchenette, and a master bedroom with a full bath.

Red Cedar Log Cabin | Romantic + Hot Tub
Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Modern Nashville Home in the Woods
Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.
Popular amenities for holiday rentals near Oliver Winery
Apartment rentals with wifi

Downtown Indy - COZY Condo - FREE|Parking

Cozy Condo at EaglePointe Golf Resort Lake Monroe.

1BR APT in the Heart of the City | LED Lights!

2 bed 2 bath upstairs unit Downtown Mooresville

Modern Top Floor Condo with State House Views

The Loft by Moondance

Spacious 3BR Condo Walkable to IU

Top Floor Loft! 4 Bedrooms and 2,000 sq ft
Family-friendly house rentals

Country home w/ fenced yard hot tub wi-fi

Cozy Home - You'll Love This Place + Garage

Nashville Treasure

Blue Limestone Cottage on North Headley Road

Lake House

Cozy Lakeside Cabin at Lake Lemon

Modern 3-Bedroom Ranch Minutes from IU Stadium!

Private, one car garage, hot coffee
Apartment rentals with air conditioning

Skyline View Condo, Best downtown spot, Park FREE!

Lil BUB's Really Nice Apartment - EAST

Couples Getaway with Outdoor Hot Tub!

Downtown Getaway ~ Historic & Peaceful, FREE Bikes

Downtown Nashville’s Chipmunk!

Hidden Cottage on Main over Ooey Gooey Café

A Stone's Throw in Little Nashville, IN

Queen Bed - Artsy, Trendy, Fun Apartment Space
Other great holiday rentals near Oliver Winery

Grandpa's Cabin at Heidenreich Hollow

Campus-Side Retreat in the Woods

Unique Barndominium studio, private Hot tub & yard

Purdy Hill Cabin

Carriage House 1 bedroom loft suite w/ fireplace.

Cheerful & Cozy Upper Cabin in Cohousing Community

Blue Lemon Bungalow - Quiet Getaway in Town!

Strawbale Bungalow. Bloomington, Indiana, USA.
Destinations to explore
- Lucas Oil Stadium
- Indianapolis Motor Speedway
- Indiana Convention Center
- Brown County State Park
- Gainbridge Fieldhouse
- The Golf Club at Eagle Pointe
- Indianapolis Zoo
- Eagle Creek Park
- Childrens Museum
- Broad Ripple Park
- Indiana State Fairgrounds & Event Center
- Monroe Lake
- McCormick's Creek State Park
- Butler University
- University of Indianapolis
- IUPUI Campus Center
- Circle Centre Mall Shopping Center
- Holliday Park
- Indianapolis Museum of Art
- Fort Harrison State Park
- Garfield Park
- Indiana State Museum
- Indiana World War Memorial
- Spring Mill State Park





