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

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.

“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

Bright Sunroom, Giant Sectional, 5 Min IU, Parking
A spotless, thoughtfully curated home designed to feel comfortable, calm, and genuinely livable — not a bare rental. Guests consistently mention the immaculate cleanliness, comfortable beds, oversized sectional, and thoughtful extras that make settling in easy. Located in a residential neighborhood, under 10 mins to IU, downtown, stadiums, dining, parks, and Kroger. This home is ideal for campus visits, couples, small groups, and professionals who value comfort, cleanliness, and a calm place.

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.

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.

Brown County Cabin near Nashville, Indiana
Boulders Lodge is a large family vacation home in Brown County (Nashville area), IN. The home sleeps up to 10 overnight guests. This private country setting is ideal for family gatherings, reunions or groups. Spacious great rooms, queen sized bedrooms, hot tub, fireplaces, pool table, large baths, kitchens and outdoor gathering areas. Secluded and surrounded by 15 beautiful acres to explore. Conveniently located to shopping, dining and entertainment in Nashville, IN and state parks.

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 | Hot Tub! + Pet-Friendly!
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.

Pine Ridge of Brown County
Welcome to Pine Ridge of Brown County. Kick back and relax in this calm, stylish space. Set on a 5 acre paradise with a well stocked cabin with all the modern amenities. Fully equipped kitchen with 3 bedrooms and 2 full, modern bathrooms, perfect for families, or a friend's getaway. Huge, pond facing deck with outdoor seating, fire pit, and Hot Tub. 11 minute drive to downtown Nashville, 13 minutes to Brown County State Park. You will love it here!

Luxe Retreat in the Woods~Theater, Gym, Hot Tub
Experience the charm of Brown County in this spacious cabin located just 20 minutes from all that downtown Nashville has to offer. Enjoy the warmth of the fireplace, unwind in the hot tub, watch a movie in the theater, stay fit in the private gym, and get cozy around the firepit. There's even a play set for the little ones to enjoy. With serene views and so much to do, there are endless activities to create your next unforgettable getaway!
Popular amenities for holiday rentals near Oliver Winery
Condo rentals with Wi-Fi

3 Bedroom Condo

2 bed 2 bath upstairs unit Downtown Mooresville

Cozy Condo at EaglePointe Golf Resort Lake Monroe.

Walk 2 Convention Ctr | Stunning Views | Penthouse

Spacious Downtown Indy Massachusetts Ave Condo

The Juke: Spacious Downtown Condo on Mass Ave!

Spacious 3BR Condo Walkable to IU

Top Floor Downtown Indy Condo • King Bed
Family-friendly house rentals

Captain Bill’s Lake House Heated Salt Water Pool

Country home w/ fenced yard hot tub wi-fi

Maria’s Haven

Bloomington Lake-View home on 40 secluded acres

Private entrance, Bright and sunny - visit IU

5BR Pool Retreat — Little 500 Weekend Available

Enchanting Dome Home - in town and in nature!

YOUnique 3+ bedroom, spa/hot tub, huge deck
Apartment rentals with air conditioning

A Stone's Throw in Little Nashville, IN

Uptown Suite Modern Studio Downtown on the Square

Couples Getaway with Outdoor Hot Tub!

Hidden Cottage on Main over Ooey Gooey Café

Private Eastside In-law Apartment

Beautiful 2 bedroom Rental Unit in Martinsville

Downtown Nashville’s Chipmunk!

Lil BUB's Really Nice Apartment - EAST
Other great holiday rentals near Oliver Winery

Garden Studio Guesthouse

Campus-Side Retreat in the Woods

Summer Kitchen at The Hill

Cozy getaway w/close proximity

Hot Tub Woodland Retreat 11 Acres + Trails Near IU

Stark Manor-Highland Cattle Farm

Hidden Retreat on 30 Wooded Acres 5 Miles to Town

Headless Goose Chalet
Destinations to explore
- Lucas Oil Stadium
- Indianapolis Motor Speedway
- Brown County State Park
- Gainbridge Fieldhouse
- Indiana Convention Center
- The Golf Club at Eagle Pointe
- Eagle Creek Park
- Childrens Museum
- Monroe Lake
- Broad Ripple Park
- McCormick's Creek State Park
- University of Indianapolis
- IUPUI Campus Center
- Holliday Park
- Indianapolis Canal Walk
- Fort Harrison State Park
- Garfield Park
- Spring Mill State Park
- Indiana World War Memorial
- Victory Field
- Eiteljorg Museum
- White River State Park
- Soldiers and Sailors Monument
- Yellowwood State Forest





