Holiday rentals in Oakland

Asa Creek Cottage

This open concept cottage offers the perfect blend of nature and modern comfort for families and small group gatherings. Enjoy the creek side deck, and listen to the gentle sound of the little waterfall nearby. On cooler evenings, gather around the fire to warm up. The interior boasts a spacious design, close to The Little Theatre on the Square, walking trails, and Lake Shelbyville with boating, fishing and swimming. Relax with a modern kitchen, 3 bedrooms, 2 bathrooms and a rainfall shower.

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

The Little Homestead Haven

Welcome to the Little Homestead Haven! Whether you are looking for an anniversary getaway or if you are traveling through the area and looking for a relaxing spot to rest, you will thoroughly enjoy your stay here. Relax and take a soak in the hot tub, while the soothing jets work the tension out of your muscles. It is located less than 2 miles east of Arcola and just off Interstate 57 on Rt. 133, 30 minutes to Champaign airport and right outside of Amish country.

The Guest House by The Trestle

A quaint and cozy cabin using all reclaimed wood. It has been a pleasure creating our dream... The Guest House. It is located on our 15 acre farmette. The barn hosts big and mini horses (ask for rides), chickens, and occasionally some bunnies. It is not unusual to spot deer, fox, birds, and other wildlife in the outdoors. Please note: Our guest house does NOT INCLUDE WI-FI OR TELEVISION. We encourage guests to unplug, relax, and enjoy the peaceful surroundings.

Countryside Guest House

Escape to a peaceful countryside retreat tucked beside a quiet pond and surrounded by open skies and nature. Wake up to serene pond views, enjoy your morning coffee outside, and spend your evenings watching sunsets, fishing, or simply soaking in the peaceful atmosphere. Inside, you’ll find a bright open-concept living space, comfortable furnishings, a half kitchen, cozy bedroom, workspace, and stylish modern finishes throughout.

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

On Harmony Lane...Cozy Loft apt in the Country

Our loft is the perfect place to rejuvenate in a country setting. From cozy bed sheets, TVs, and Wi Fi inside, to a firepit, grill, and hammock chairs outdoors, we make your stay comfortable. We are minutes from Eastern Illinois University. So enjoy...go antiquing, visit a winery, or delve into Lincoln's history. Visit a nearby Amish town. Go kayaking, fishing or enjoy a hiking on a nearby trail or one of ours.

Simply Savvy

Charming 1 bed, 1 bath home with everything you need for a relaxing stay. Enjoy a full kitchen, in-house laundry, cozy living room, and a spacious bedroom with en-suite bath. The inviting front porch is perfect for morning coffee or evening sunsets. Located on a large lot near downtown with plenty of parking and fun nearby activities. Ideal for both weekend getaways and extended stays.

The Village Retreat

Wake up to the quiet, laid back village life, sip coffee while enjoying the peaceful outdoors, and unwind under starry skies at night. Perfect for travelers seaking a unique getaway, this stay offers character and tranquility. Whether you're here for a weekend escape or a longer adventure, this rare find promises a memorable experience.

Griff’s Knob

Check out this rustic tower! There is something unusual everywhere you will look. Each of the 4 floors are a different room. The views from the top are outstanding. Between the leaves changing, snow, and wildlife there is always something beautiful to see. This is a fun stay that is anything but ordinary.

The CaBIN

Unwind in a truly unique converted silo, tucked away in a peaceful forest just 5 miles from town. Surrounded by abundant wildlife and minutes from the state park, this rustic retreat is perfect for families, friends, or adventurers seeking a blend of quirky charm and outdoor adventure.