Holiday rentals in Dolan

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Top-rated holiday rentals in Dolan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern home is showcased with a welcoming porch and screened-in area. Wooden decking surrounds the entrance, providing accessibility. The structure is set against a clear blue sky, with a manicured lawn and trees in the background, highlighting a serene country environment.
Home in Bloomington
4.99 out of 5 average rating, 93 reviews

Cozy getaway w/close proximity

Relax as a couple or w/friends or w/family at this secluded cozy getaway. Several scenic views from inside home & from porches. Home sits near I-69 offering over a 2 mile panoramic view. Whole home has been updated w/addition of a large porch & screened in porch. Conveniently located in close proximity to IU & downtown, tho located on a private road in a scenic country setting. Also, located near to hiking trails, biking routes, playgrounds & golf courses. Approximately 3 miles from IU stadiums.

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, 300 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, 207 reviews

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.

Top guest favourite
A sprawling green field stretches towards the horizon, filled with soft clover and dotted with trees. In the foreground, a planter holds bright flowers, adding colorful contrast to the natural landscape. The sky is lightly clouded, enhancing the serene atmosphere.
Guest suite in Bloomington
4.98 out of 5 average rating, 169 reviews

Peaceful apartment space in beautiful farm house

Our lovely farmhouse is minutes from Lake Lemon, Griffey Lake, Indiana University & many spots in Bloomington. Conveniently not far from I-69, we're 20 minutes away from Nashville. This is a basement apartment with private bedroom, private bathroom, large living/dining area, & kitchenette. Shared front door & ~10 steps inside main floor. The ranch is 50+ acres with 8+ acres of woods for hiking, pastures with cattle, a heated pool & patio area, & a beautiful front porch looking over the ranch.

Guest favourite
A front porch is featured, adorned with hanging ferns and string lights, creating an inviting atmosphere. A wooden railing surrounds the porch, which includes seating and a dining table. Bright flowers are planted in decorative boxes at the base, complementing the lush green yard.
Bungalow in Bloomington
4.93 out of 5 average rating, 399 reviews

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.

Top guest favourite
Home in Bloomington
4.99 out of 5 average rating, 197 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.

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, 501 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.

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
4.94 out of 5 average rating, 178 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
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, 231 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
The exterior of the cabin showcases a rustic log structure with a green metal roof, surrounded by lush greenery. Two wooden rocking chairs with colorful cushions are positioned on the porch, inviting relaxation. Large windows provide a glimpse of the peaceful woodland setting.
Cabin in Nashville
4.96 out of 5 average rating, 123 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 spacious living area features exposed wooden beams and a stone accent wall. Comfortable seating arrangements are placed around a central coffee table, with a television mounted above a console. Soft lighting enhances the warm wood tones throughout the cabin.
Cabin in Bloomington
4.93 out of 5 average rating, 159 reviews

Campus Castle Guest Villa

ROMANTIC COZY CABIN 2 blocks from the IU Football stadium . Two guests only. Fun lodging alternative. YoutubeTV, Slots, Pacman, Rod Hockey,pinball,etc. - ON FOOTBALL WEEKENDS we allow 4 guests. Save hundreds on game day parking fees. -30 years old min age to book. -LOFT BED UPON REQUEST BEFORE BOOKING ONLY: IU parents visiting their IU kid. If you message us , we can provide a self service twin bed in the loft(bed sheets provided) .

Popular amenities for Dolan holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Monroe County
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