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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.

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Guest favourite
The evening view of the home's exterior reveals a modern design with wooden accents. Soft lighting highlights the elevated deck and entryway, and the surrounding trees create a serene atmosphere. Stairs lead to the entrance, providing access to the spacious interior.
Cabin in Unionville
4.96 out of 5 average rating, 299 reviews

“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

Top guest favourite
Cabin in Unionville
5 out of 5 average rating, 205 reviews

Summer Forest Reset: King Beds & Lake Lemon Marina

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, this custom log home 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.

Top guest favourite
Home in Bloomington
4.99 out of 5 average rating, 193 reviews

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.

Guest favourite
A spacious deck is seen, featuring a circular table with four cushioned chairs and a large umbrella providing shade. Surrounding greenery is visible, adding a natural backdrop to the outdoor space.
Home in Bloomington
4.89 out of 5 average rating, 105 reviews

House Around the Corner

Located on a country cul-de-sac, this recently remodeled house is a great place for a get-a-way. This house has 5 bedrooms and 2 bathrooms, not including basement mother-in-law suite that is rented separately, is 2 min to Butler Winery, 10 min to Lake Lemon Beach, and is 15 min to Oliver Winery. Get to the east side of Bloomington in 15 min or get to Nashville in less than 30 min! Spend a day out enjoying the attractions or spend time relaxing on the large, beautiful deck overlooking a ravine.

Guest favourite
A living area is displayed with a comfortable sofa and patterned armchairs, offering spaces for relaxation. Natural light enters through large windows, illuminating the wood-beamed ceiling and highlighting the rustic wooden accents. A small table and television are positioned for convenience.
Bungalow in Bloomington
4.98 out of 5 average rating, 123 reviews

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.

Top guest favourite
The entrance to the cabin features a covered porch with rustic wooden supports and decorative string lights. A welcoming outdoor seating area is visible in the background, surrounded by lush greenery and shaded by nearby trees. The path is lined with stones and small plants.
Cabin in Unionville
5 out of 5 average rating, 498 reviews

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.

Top guest favourite
An open living area features warm, brown leather seating arranged around a dark coffee table. A large TV is mounted on the wall, while a dining table with black chairs sits in the background, under a modern light fixture. Light wood flooring completes the space.
Home in Bloomington
4.95 out of 5 average rating, 170 reviews

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.

Top guest favourite
The living area features wooden walls and ceilings, complemented by large windows that allow natural light to illuminate the space. Two seating areas include a brown sofa adorned with cushions and a rust-colored recliner, alongside a coffee table. A dining area can be seen in the background.
Cabin in Martinsville
4.91 out of 5 average rating, 514 reviews

Grandpa's Cabin at Heidenreich Hollow

Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!.

Top guest favourite
A charming guest suite set against a backdrop of lush green trees. The single-story structure features a covered porch, large front windows, and a welcoming entryway, immersed in the tranquility of the natural surroundings.
Guest suite in Bloomington
4.95 out of 5 average rating, 227 reviews

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.

Top guest favourite
A modern kitchen is featured with dark cabinetry and open shelving displaying dishes. A patterned backsplash adds visual interest, while stainless steel appliances, including a refrigerator, microwave, and dishwasher, provide functional amenities. A vase of flowers brings a touch of color to the countertop.
Guest suite in Bloomington
4.99 out of 5 average rating, 147 reviews

Campus-Side Retreat in the Woods

Across the street and walking distance to IU's sports facilities, this chic and modern wooded retreat is a short drive or bike to downtown Bloomington's vibrant nightlife and community activities. The studio apartment boasts a skylit bathroom, a full kitchen with custom-made cabinets, washer/dryer on site, and professional decorating. It’s only a short drive, or slightly longer hike to Griffy Lake, only one mile to IU Health Bloomington hospital, and minutes to I69.

Top guest favourite
Cabin in Nashville
4.96 out of 5 average rating, 120 reviews

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.

Top guest favourite
A modern home is positioned on a hillside, featuring a sleek black exterior and large windows that allow for ample natural light. A balcony extends from the structure, providing outdoor seating and a view of the surrounding trees.
Cabin in Nashville
5 out of 5 average rating, 518 reviews

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

  1. Airbnb
  2. United States
  3. Indiana
  4. Monroe County
  5. Bloomington
  6. Oliver Winery