
Holiday rentals in Monticello
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Monticello
Guests agree: these stays are highly rated for location, cleanliness and more.

Horseshoe Hideaway on the Tippecanoe River!
Rest & Relaxation await you at Horseshoe Hideaway! This bright, open space is ready to host you for your next adventure! Located in the secluded Horseshoe Bend area of the Tippecanoe River, this house is able to host a variety of guests with 3 bedrooms, 2 full bathrooms, fully equipped kitchen, smart TVs, electric fireplace, large deck, & washer/dryer. Off street parking is available. This home offers peace & quiet while still being close to amenities & many outdoor activities! Come visit today!

Lazy Lake Life Awaits!
Relaxing Lake House retreat perfectly situated on a 1/2 acre wooded lot with views of the lake! Minutes away from Indiana Beach, White Oaks, Madam Carroll, Oak Dale Dam and many other local attractions. Kick back on the wraparound decks while you bbq or watch the gorgeous sunsets. Enjoy a morning cup of joe while listening to the sounds of music-birds in this treehouse like setting. After a long day on the lake enjoy a nice soak interior jacuzzi tub big enough for two! Great winter getaway too!

*Award Winning-Victorian Home(Large outdoor space)
Open & lit for recreation & relaxation. 2 car private parking area directly on side. Wrap around porch & garden for entertaining, grilling, & conversation. Large kitchen(seating 4), dining area(seating 8) and parlor for entertaining (seating for 6). Living / TV Room with Apple TV to watch NETFLIX & TV(no cable). Multiple work desks w/ area for reading & relaxing in office & master bedroom. Large bedrooms w/ built in storage / closets. Stand up showers & bathrooms w/ towels / provisions in each.

10 mins to Purdue, vacation amenities!
Gather around the campfire at this peaceful 1-story home. Completely renovated! The perfect place to cookout and just hangout with your group! Screened in porch, gas grill, fire pit area,large backyard. Outdoor lighting creates ambiance for night time entertaining. Inside is spacious and bedrooms away from main living area. Sun room is great flex room:playroom/sleeping porch. Large dining table seats 8, fully stocked coffee bar. 1 King , 2 Queens, 3Twins. Tippecanoe Co. STR Permit# TR-07

King Sized Overlooking The Heart of Downtown
OVERLOOKING DOWNTOWN MAIN ST! Situated in the Arts and Market District of downtown Lafayette, this 1 bedroom, 1 bath, unique, modern apartment is newly renovated and hosts an open concept with extremely high ceilings and a beautiful accent wall. Apartment is located directly in the Heart of Downtown Lafayette, just minutes from Chauncey Village District on Purdue University's campus, Ross-Ade Stadium, and Mackey Arena. This is truly a prime location for a Lafayette, IN/Purdue University visit.

Lake Shafer 3 bedroom 2 bath lakefront house
Relax in our 3 bed 2 bath lakefront cottage in the heart of Lake Shafer. Enjoy several outdoor seating/eating areas and the party deck that overlooks the lake. Come nightfall, throw some logs into the fire pit and enjoy the lights and sounds of lake life! 2 kayaks with life vests included. Cottage is walking distance to Indiana Beach, Tippecanoe Country Club golf course, putt putt, arcade and basketball courts. Sorry but no pets and no parties. Cottage is in a quiet residential neighborhood.

Relaxing Lake Freeman Cozy Cottage, Large Deck
Get away from it all in this quaint 3 bdrm cottage (on the canal / inlet) leading into lake freeman. peaceful views, fantastic deck with fishing access. No direct swimming access. Conveniently located - walking distance to Madam Carroll, Sportsman, Kopecetic Beer Factory. Indiana Beach - less than 15 min. Purdue 30 min. Feel right at home & ready to relax! Sit around the quiet firepit, You wont want to leave the lake life! Friendly Neighborhood is walkable or bring a bike to enjoy.

Historic Industrial School House
Stay in a one-of-a-kind historic gem just 4 miles from Purdue, located on the edge of town with easy access to shops and dining. Built in 1890 as a schoolhouse, this updated 1BR + loft blends original charm with industrial style and modern comfort. Backing onto woods and an active train track, it offers a rustic countryside feel. Next door is a historic cemetery, and a nearby correctional facility adds unique character. Relax in the spacious yard and firepit after a day of exploring.

Oak Grove Place (2 King Beds) on 5 acres
Fully furnished, large country house. With beautiful country views. Large wrap around front Porch and back deck. Perfect for picnics or just relaxing. Ideal location for any size of family or group. Two king beds, one queen, one full size bed plus a queen sleeper couch to meet a large family needs. During winter months you can enjoy the warmth of the fireplace. Wood is provided. (For small groups that use no more than 1 bedroom please contact us for a special rate.)

The Rock House in Delphi - Rock Solid. Charm.
The historic Rock House is full of the character and charm of a classically-styled bungalow — window seats, a rock fireplace, and artfully designed living areas. Furnished for comfort, certain to charm. Guests can enjoy relaxing with cocktails, cooking in a fully furnished kitchen, or using a tandem bike to explore the neighborhood. Fido is welcome too. This two bedroom, one bath, home offers all the modern amenities for a comfortable stay.

A Fairytale Farmhouse at Farm to Folklore
110 year old farmhouse filled with mystery and wonder. If you enjoy fairytales, folklore, nature, and love books then this is the getaway for you. 40 acres to explore and friendly animals to enjoy. We are a family run, working farm and enjoy saying hi and interacting with our guests! We also have another Airbnb listing the Historic Schoolhouse Loft. It can be rented along with the house for extra large groups. Check it out!

Cottage on Lake Freeman
3bedroom 1bath living room along w dining room full kitchen and laundry room. 65 ft of water frontage with dock. there is a gas grill along w fire pit on deck with lots of seating. We also have a tiki bar. THIS IS A HOUSE RENTAL ONLY. We have our personal electric boat lifts you can use when renting the house. 65ft of shore front that is exclusive and private to abnb renters for laying out and swimming.
Popular amenities for Monticello holiday rentals
Stay near Monticello's top sights
Other great holiday rentals in Monticello

CozyCabin

Panoramic view on Lake Freeman!

Contemporary Cozy Apartment

Hot Tub + Bonfires | Lake Shafer Waterfront

Riverside Retreat

Stay & Play at Indiana Beach!

Mthly Disc Rates Avail 10/01/25-04/30/26 2Bd

Two bedrooms Cottage #1 Perfect for Families!
Quick stats about holiday rentals in Monticello

Total holiday rentals
Explore 10 holiday rentals in Monticello

Nightly prices starting at
Monticello holiday rentals start at £53 per night before taxes and fees

Verified guest reviews
Over 480 verified reviews to help you choose

Wifi availability
10 of Monticello holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Monticello rentals

4.8 Average rating
Monticello stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Chicago Holiday rentals
- Northeast Ohio Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Detroit Holiday rentals
- Southern Indiana Holiday rentals
- St. Louis Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals




