
Holiday houses in Fair Oaks
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Top-rated holiday rentals in Fair Oaks
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Luxury Cabin Getaway •2 min to Beach• 1hr Chicago
Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

Cathy's Little Farm Loft
Cathy's Little Farm loft is a 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn, gardens, and chickens to enjoy.

UncleLarrysLakePlace HotTubKayaksPingPong
A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

Saint Rayburn's Place
Our space is in a small but fantastic town, perfect for couples, solo adventurers, business travelers. Rensselaer's unique art scene is renowned; check out over two dozen murals that grace our revitalized downtown. Play disc golf at Brookside Park-we have discs for guests' use! Our listing fee is what it is-no separate "cleaning fee." We'll always leave you with homebaked goodies, & make sure there are farm fresh eggs in the fridge. When you're ready to relax, head to Saint Rayburn's Place.

Quiet Farmhouse Retreat
Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country
Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

Tiny Home on Organic Veggie Farm
Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

The Loft at Virgie
You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Country Cottage
Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Rainbows End 🌈 Plensa
Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Home of 1888
Conveniently located 6 1/2 miles from I-65 between the Lowell and Roselawn exits and 6 miles from Sandy Pines Golf course & The Pavilion. This fully updated place has everything to feel right at home. The kitchen is provided with everything you need to prepare a meal. Plenty of places to eat out are just down the street. A 43" Samsung smart TV with Sling TV and Paramount Plus. When it's time to rest you'll do so on a brand new Nectar memory foam beds.

Rustic Lodge -Oak Tree Lodge
The Oak Tree Lodge is located in a country setting and offers a private lodge with an outdoor area for relaxing and entertaining. The former barn structure has been beautifully transformed in a rustic and comfortable lodge to rest, relax, and renew. We have renewed it into a fresh new life - as a lodge to invite friends and guests to enjoy and relax. The listed rate is for four people, and additional quests will be $25.00 per person.
Popular amenities for Fair Oaks holiday rentals
Other great holiday rentals in Fair Oaks

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

Technicolor River Retreat just outside of Chicago!

Tippecanoe River Retreat

3 Bedroom River Retreat with lake access

Historic Cabin Hideaway: Woods & Charm

The Jefferson House

A Glass House in a Gated Nudist Resort

Charming Country Cottage
Destinations to explore
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