Holiday rentals in Grundy County

The "Doddy" House

Take a weekend....or a week! Travel back in time to Jamesport Mo and stay at this cozy 1 bedroom,1 bath Suite in the middle of Amish Country . Located 4 miles east of Jamesport ,this peaceful setting is sure to turn your week around! Enjoy the sunset and go for a walk, or take a tour of Mrs. Mary's Amish home... Why the "Doddy" house? Doddy houses are usually the second dwelling on an Amish farm. Generally small and built to accommodate the elderly parents after they pass on the farm to a child.

Anna's Room The Porch @ Sherwood Crossing

Save here. No cleaning fee! Your space includes a room with two very comfortable queen size beds, private bathroom and a very generous living room. Our home is on five acres within 25 minutes of Chillicothe, Trenton or Hamilton. We are in an area surrounded by Amish neighbors so chances are you’ll see a few buggies while you’re here. Lots of opportunity to relax on our covered porch with two person hot tub, back deck or large above ground intex pool. Nature abounds.....trees, birds, horses.

The Inn on Main - Boutique BNB

Escape to this stylish and serene boutique airbnb, perfect for couples seeking a cozy, romantic getaway. Thoughtfully designed with warm tones, plush furnishings, and elegant accents, this space is ideal for unwinding together. Curl up on the luxurious leather sofa with a glass of wine or enjoy a candlelit dinner under the sparkling crystal chandelier. Whether you’re celebrating a special occasion or simply taking time for each other, you’ll find the perfect setting here. No pets allowed

5 stars. Sleeps 5. Filtered water. Lots of parking

Relax at Grandma's Cottage. Convienient. Calm. Clean. Lots of parking. * desk * roku tv * sleeps 5 adults. +2 children * Extra kids mattresses * Pack-n-play for baby * toys * closets * extra blankets * filtered drinking & shower water * celling fans * washer/dryer * toilet/shower bar * storm shelter * off street parking Enjoy outdoors * large yard * fire pit * swing set * bbq close to *shopping *groceries *walking trail *high school *shady park *fair grounds *restaurants *& more

Lake House: 3 BR, 3 Bath w/ handicap adaptations

NO LAKE ACCESS! The house has views of Trenton LAKE from several areas of the property! Spaces bring the OUTDOORS.. IN, with wildlife furnishings throughout. ENJOY your time by sitting on the enclosed porch or outdoor patio. Use the fully stocked kitchen to create delicious meals. RELAX in one of two living spaces. Office space, comfortable beds, spacious bathrooms, in house laundry. We hope you get out and EXPLORE what the area has to offer! Handicap Adaptations

Oaktree Ridge

2 bedroom apartment on 2nd floor. Living room with wall mounted 55"TV, kitchen, bathroom with washing machine/dryer. Wi-fi available. Linens provided. Kitchen stocked with basic cooking gear. This apartment is located in town. We are located walking distance from Eastside park, the city walking trail, grocery stores, and fast food restaurants. We can host up to 4 people. $10/per person per day fee for 2nd and 3rd persons (including children).

Adorable 1 room lake cottage with free parking.

Peaceful lake cottage on 5 acres of lakefront property. Parking on premises. Walking distance to the Black Silo Winery. Beautiful surroundings. Perfect place to get away and relax. Includes Fiber Internet. Private owned lake for your viewing pleasure only. There is no water access included for guests. Yard and gazebo with table and chairs available to use. Sanitized and cleaned with covid precautions in mind.

Whispering Waters

Relax with the whole family at our cabin on the lake. Bring your swimming things and fishing gear and get ready for a good time! You can feed the fish, grill a delicious meal, relax in front of the tv, or soak up the sun in the water or on the sand. Spending time with friends and family on the lake will be time well spent. We also have 2 kayaks and a small fire pit there you're welcome to use.

Silo View (Entire Home)

Welcome to our charming two-story farmhouse, over 100 years old and ideally located across from the picturesque Black Silo Winery. Ideal for weddings, family or friend visits or simply enjoying a trip to the winery which features ample parking for your convenience. Enjoy the spacious backyard, a covered patio, and a welcoming porch- ideal for morning coffee or outdoor gatherings.

K4C Premier Cottages - The City Loft

The City Loft is our two-story city escape, a little piece of NYC right here in the heart of the Midwest! Featuring an open concept, studio floor plan, the City Loft is contemporary meets industrial. Located off Hwy 65 our cottages are easily accessible with no through traffic. The City Loft has a private porch with a sitting area, perfect for enjoying your morning coffee.

BOHO In The Countryside!

Escape the town’s hustle and find your serene retreat at this unique dome home, tucked away just outside of town. Surrounded by peaceful woods and open fields, it’s the perfect balance of seclusion and convenience. Enjoy the calming sounds of nature, unwind in a cozy, boho-inspired space, and reconnect with yourself—without ever being too far from everything you need.

The Cabin at the Orchard

Take it easy at this unique and tranquil getaway. Unplug and unwind in the heart of a peaceful, 1,200-tree working apple and peach orchard. Whether you're sipping coffee on the porch, wandering through rows of fruit trees, or just soaking up the quiet on the beach, this serene escape offers the perfect spot to slow down and recharge.