
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.

“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.

Bright Sunroom, Giant Sectional, Parking, 5 Min IU
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.

Cheerful two bedroom Farmhouse with free parking
Your family will be located in a lovely Bloomington rural setting that is less than 10 miles from Indiana University and less than 5 miles from beautiful 10,750 acre Lake Monroe. You will be able to unwind on the front porch swing, relax on the spacious back deck or warm your hands and feet by the fire pit provided. If you are a foody you are within 10 to 15 minutes from the many Bloomington restaurants or if you prefer the cooking option there is a full kitchen for your culinary creativity.

French Cottage Style 3 bed, 1 bath house
Add my listings to your wishlist by clicking the ❤️ in the upper right corner. You and/or your family will be close to everything when you stay at this centrally-located home in a very quiet neighborhood. Extremely close to IU No bonfires of any kind!!! We allow dogs but no cats. Fully fenced in back yard. Want to check in early? $20 convenience fee for early check in. Leave on counter when you check out Absolutely no smoking inside the house and no gatherings larger than 8 people!

I.U. Museum/Gallery-Cascade’s 12th Hole Golf Club!
Relax with the whole family at this peaceful house across the street from Hole 12 of Cascade Golf course. Right next to Bloomington North High School. Very close to Lower Cascade Park with a beautiful waterfall. 3 bedrooms with a fenced in back yard. The house is a 2 minute drive to Kroger grocery store, Avers Pizza and Subway Sandwiches. Memorial Stadium is also on the north side and easily accessible. Taking College Ave will have you right downtown and to Indiana University in no time

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.

Covered Bridge Cabin (on Big Walnut Creek)
Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

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.

Nashville Treasure
This mid-century modern one bedroom house is located just 15 minutes from historic Nashville. Beautifully decorated and adjacent to Yellowwood State Forest. This house has an open floor plan. The large kitchen is open to a large family room. You can lounge in comfort or sit on the back deck and watch the wildlife. Newly remodeled in 2019 it is a sight to see. You will be making plans for your next visit.
Popular amenities for holiday rentals near Oliver Winery
Condo rentals with Wi-Fi

Cozy Condo at EaglePointe Golf Resort Lake Monroe.

3 Bedroom Condo

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 Downtown Indy Condo • King Bed
Family-friendly house rentals

The Loft House - 3 Bedrooms - IU Bloomington

Country home w/ fenced yard hot tub wi-fi

Blue Limestone Cottage on North Headley Road

Captain Bill’s Lake House Heated Salt Water Pool

There's No Place Like Dome!

Harmony Hills 3 bedroom farm house

Brown Co Getaway: Sleeps 10-Hot Tub-Firepit-Grill

Maria’s Haven
Apartment rentals with air conditioning

Uptown Suite Modern Studio Downtown on the Square

Lil BUB's Really Nice Apartment - EAST

Downtown Nashville’s Chipmunk!

Couples Getaway with Outdoor Hot Tub!

The Nigh Place, Studio Apartment, King Bed, 55"TV

Modern & Bright in Prime Location

A Stone's Throw in Little Nashville, IN

Private Suite, Sleeps 4, 1 mi to Downtown & Park
Other great holiday rentals near Oliver Winery

Grandpa's Cabin at Heidenreich Hollow

Stark Manor-Highland Cattle Farm

Cozy getaway w/close proximity

Brown County Woods - Cabin 2 king beds Secluded

Carriage House 1 bedroom loft suite w/ fireplace.

Strawbale Bungalow. Bloomington Indiana USA.

Loft Apartment: Beautiful Farm and Country Views

Hidden Retreat on 30 Wooded Acres 5 Miles to Town
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
- Indiana State Fairgrounds & Event Center
- Monroe Lake
- Broad Ripple Park
- McCormick's Creek State Park
- Butler University
- University of Indianapolis
- IUPUI Campus Center
- Circle Centre Mall Shopping Center
- Holliday Park
- Garfield Park
- Fort Harrison State Park
- Spring Mill State Park
- Indiana State Museum
- Indianapolis Canal Walk
- Indiana World War Memorial





