Holiday rentals in Wooldridge

Charming 3 Bedroom Cottage in the Countryside

Our house is the perfect getaway for a family, group of friends or a couple. The lake and gardens around the house provide the quiet and peace of a retreat place, away from the busyness and distractions of the city. It's a very pretty drive to Columbia, MO (about 30 minutes), and 20 minutes to Rocheport, a very cute historical town by the Missouri River. A beautiful attraction that is close to our property is the Warm Springs Ranch. The Clydesdale breeding farm. This is a great place to visit.

Value · Family · Hiking

Bluff House in Rocheport Missouri

The Bluff House faces the Missouri River on 7 acres of beauty, neighboring the Bougeois Winery! The Katy trail & Rocheport are 1 mile away. Our home is two stories. We are upstairs and the Air BNB is downstairs. The Airbnb has a spacious living room, fireplace and dining room. All with views of the river and an open concept kitchen. Your entrance is completely separate and locked for use only by you. You will have a private covered deck, Bench on the bluff, Bikes, Fire pit and a Hammock!

Value · Location · Biking

The Fox Cottage

Welcome to our cozy retreat in the heart of Columbia. Home of the Mizzou Tigers, True/False Film Festival, Katy Trail, historic downtown, and much more! Located within a 1 mile drive to downtown, your home away from home includes off-street parking, 3 bedrooms, 2 full bathrooms, kitchen, living room, dining room, patio, and fenced back yard. We offer complimentary coffee, snacks, and a selection of board games, vinyl records, and streaming services. Certificate of Compliance License #ONS025545

Family · Location · Grill

Step Back in Time Near The Missouri River!

Be transformed back in time in this home that was built in 1904 filled with historic charm. Relax at this tranquil getaway! It's so quiet you can hear the gentle river rolling by! This home is located just steps away from the banks of the Missouri River, in the small town of Lupus, MO. The property is surrounded by nature and many beautiful flower gardens. Lupus has as much charm as the house. Sit on the porch and watch fireflies in the evening, relax on the deck or grab a seat by the river!

Family · Location · Decor

Upscale country living at its finest! Pool,HotTub

Nestled onto 10 peaceful acres, w/pond about 15 minutes to downtown Columbia and the University, close to restaurants, and activities, that is if you want to leave the Pool and the quiet of the country. 8 beds, + a few air mattresses, plus 2 pack/plays. You'll love the kitchen, the peace, and the coziness. The in-ground heated pool is 25 x 50 feet. (Closed mid Oct. - mid April) We stock wood for the fire pit, so roast hot dogs, or make S'mores! No parties! No unregistered visitors please.

Value · Family · Amenities

Cozy 2 Bedroom close to University

Experience comfort and convenience at our charming home in the heart of Columbia. Enjoy spacious rooms filled with natural light, cozy beds, and a fully equipped kitchen. Centrally located, our home offers a backyard retreat perfect for relaxing evenings with room to run and play. Walk to top-rated restaurants and coffee shops or take a quick drive to downtown and the University. Ideal for visiting families and university guests alike, our space promises a memorable stay here in COMO!

Value · Family · Access

The WhiteHorse Guest House

Come enjoy this lovingly restored 1895 home on the National Register of Historic Places, located in the heart of historic Rocheport, Missouri. The home is filled with American country antiques and hooked rugs. There are two bedrooms with queen beds, a fully stocked kitchen, brick patio and hot tub. The home is blocks away from the Katy Trail, shops and restaurants. Nominated by the magazine, Inside Columbia, as one of the top 5 places to stay in the Columbia area for 2026.

Location · Value · River

Bohemian Tiny House

BOHEMIAN-Socially unconventional, artistic, literature, freedom, social consciousness, healthy environment, recycling, intimacy with nature, supporting diversity and multiculturalism. TINY HOUSE-Small dwelling & footprint, lower costs, energy savings, intentional design. If you are not comfortable with the intimacy of nature, a walnut forest, & wildlife, we may not be the right fit for each other. We love hosting and just request you respect our philosophy & cherished space.

Family · Value · Parking

Charming Suite off West Broadway

Entire lower level of home with 2 beautiful large bedrooms, spacious bathroom with lots of hot water in shower! Beautiful fireplace in gorgeous living area with dining area. Kitchenette includes refrigerator, toaster oven, microwave and Keurig coffee maker This lower level apartment is light and airy with large windows in each room! Bedrooms include televisions along with big screen TV in living area. Private outdoor sitting area with fire pit to enjoy your evenings!

Value · Location · Accuracy

Kit Carson’s Cottage at the trail walk to downtown

Near I-70 and the trail! Your cottage is steps from the trail and 3 blocks to downtown dining, shops and galleries. Stay comfortably with 2 bedrooms, queen memory foam sofa sleeper, 1.5 bath, garage, deck, 1920's themed lounge with hidden door and more here in historic Rocheport! TV, Wi-Fi and Bluetooth soundbar and large backyard with garden igloo available for your entertainment. One night stays available upon request.

Family · Value · Nearby

Just off the beaten path

Take it easy at this unique and tranquil getaway. 5 minutes from I-70. Enjoy nature in the woods in our cozy, quiet guesthouse. Close to the University of Missouri for events, medical and business travelers, as well as the Katy Trail for cyclists, wineries, and I-70 for the weary traveler needing a quiet rest and relax. Coffee/tea to wake up enjoying breathtaking views from your private deck.

Value · Location · Quiet

Cozy, Rustic Cottage Pet-Friendly South Columbia

A cozy homestead retreat backs up to 50 acres of woods. Two bedrooms can sleep up to 4. Full kitchen. Laundry in basement. Just 15 minute drive from downtown Columbia, one minute from gas stations and Dollar General- so convenient. Great for game day visitors, families visiting their university students, a retreat space, and more!

Family · Location · Amenities