Holiday rentals in Wooldridge

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Top-rated holiday rentals in Wooldridge

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Top guest favourite
An interior view of the Bunk House showcases two twin bed frames adorned with quilts in various colors. Soft pillows are arranged on each bed, while a large window allows natural light to illuminate the space. Air-conditioning unit is visible on the wall.
Farm stay in Holts Summit
4.92 out of 5 average rating, 287 reviews

The Bunk House

The Bunk House is an 8 by 12 foot shed with 3-4 bunks. There is a twin sized bed across the back, a bunk sized bed on each side and a plank to pull out to accommodate a fourth person in the middle over the walkway. With this adaptation, you have an 8 by 10 foot bed. We provide foam mattresses, sheets, blankets and pillows. There is an air-conditioner and a heater. Bucket toilet behind the bunkhouse. Fire ring available. No pets. The water is from our deep well - tested, certified and delicious!

Guest favourite
An entryway features a round table with a decorative vase and a small plant. Framed artwork adorns the walls, while a blue couch with decorative pillows is positioned in the background. Soft lighting highlights the cozy atmosphere.
Home in Jamestown
4.82 out of 5 average rating, 191 reviews

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.

Top guest favourite
A peaceful view of the Missouri River glistens under the sunlight, seen from a private deck. Lush greenery lines the foreground, and gentle hills can be observed across the water, creating a serene natural landscape.
Home in Rocheport
4.98 out of 5 average rating, 559 reviews

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!

Guest favourite
The exterior of the tiny house showcases a raised terrace with two chairs, providing a relaxing spot to enjoy the view. A staircase leads to the entrance, with trees offering shade nearby. The house features a simple design with large windows for natural light.
Tiny home in Jamestown
4.93 out of 5 average rating, 148 reviews

Teeny Tiny Getaway in the Missouri countryside

A tiny house on a “micro” level. Comfy and cozy with a spacious view of nature. If you’re looking for a unique space to be alone to meditate or just simply to have a few days by yourself this is the spot for you. In the country side away from the busyness of life this gem offers a peaceful get-away. Equipped with WiFi, AC, ambient back-lit heating, folding table, a smart flat screen TV, filtered hot and cold water, microwave and refrigerator. A beautiful view perfect for stargazing. Welcome :)

Top guest favourite
A screened-in porch offers a serene view of the lake, surrounded by greenery. Comfortable seating is arranged around a glass-top table on a vibrant rug. A hammock hangs nearby, inviting relaxation in a tranquil setting.
Guest suite in Columbia
4.99 out of 5 average rating, 404 reviews

Lakeside Cottage Guest Suite

Huge guest suite with beautiful lake views centrally located close to MU, the MKT trail, and just about everything else Columbia has to offer! Enjoy the outdoors via the dock, fire pit area, screened in porch and hammocks. This private guest suite is the entire lower level and offers a large great room with full kitchen and two large bedrooms. Each bedroom has access to a bathroom and sink and there is a combination shower/jetted tub between. Stylish decor. Come stay and leave refreshed.

Guest favourite
A charming Tiny House is nestled among trees, featuring red doors and a porch with railing. A staircase leads up to the entrance. A yellow chair sits on a brick path in the green yard, surrounded by lush foliage and a natural setting.
Tiny home in Columbia
4.89 out of 5 average rating, 815 reviews

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.

Top guest favourite
A covered patio area features a colorful hammock and a wooden dining set, surrounded by green grass. The patio is adorned with decorative string lights, offering a cozy atmosphere. The exterior of the building is light-colored, with large glass doors leading indoors.
Flat in Rocheport
4.99 out of 5 average rating, 112 reviews

The Katy Trail Carriage House

Such a tranquil and serene apartment in the lovely town of Rocheport. Only two blocks away from the Trail as well as Meriwether Cafe! You will not be disappointed with this location and amenities. A lovely bedroom and kitchenette with private bath.. A nice place inside for your bicycles in the attached converted garage / living space. (Separate from bedroom) . Light breakfast options include breakfast bar, oatmeal, nut/fruit packet, coffee, tea, juice.PETS NOT ALLOWED.

Superhost
A rustic front porch features wooden paneling illuminated by hanging lights. Two wooden chairs are positioned beside a wreath-adorned door. A broom rests against the wall, while a wooden crate holds antlers, adding character to the welcoming entryway.
Farm stay in California
4.9 out of 5 average rating, 298 reviews

The Shouse

The Shouse is a rustic living quarters built directly under the same roof as our horse stable. Bring your horses along and they can stay here too. The home has recently been fully renovated from an Amish tack shop. It is located in the heart of an Amish community. Spend your evenings relaxing on the front porch and watch the horse and buggies go by. Ask about booking your own buggy ride while you stay to get the most out of your visit!

Guest favourite
A serene bedroom features a spacious bed with a decorative headboard and layered bedding. Natural light filters through wooden shutters, illuminating the antique wardrobe and wooden table adorned with a decorative item. A stylish chandelier adds an elegant touch to the warm wooden floors.
Home in Rocheport
4.95 out of 5 average rating, 263 reviews

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.

Guest favourite
A well-equipped kitchen area features green cabinets and a white countertop. Open shelving displays various dishware and decorative items, while a clock and a microwave are positioned on the counter. A refrigerator stands at the end, and bins for trash and recycling are neatly organized below.
Guest suite in Columbia
4.9 out of 5 average rating, 237 reviews

Large Private Guest Apt Close to Campus & Downtown

Private guest quarters are set-up in a basement Mother-In Law Suite with private entrance and amenities. Newly refinished two bedroom, one bathroom, fully equipped kitchen and entertaining space fully accommodates up to five adults. One bedroom has a queen size bed and the other has two twin beds. Located close to downtown and within walking distance of the stadium, restaurants, coffee shop, and more.

Top guest favourite
A charming historic house is showcased with a light-colored exterior and grey metal roof. A stone pathway leads to the entrance, bordered by well-manicured grass and seasonal flowers. Decorative lanterns and a welcoming sign enhance the home's inviting presence among mature trees.
Home in Rocheport
4.99 out of 5 average rating, 172 reviews

The WhiteHorse Guest House

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 functional kitchen, patio and new hot tub. The home is blocks away from the Katy Trail, shops and restaurants.

Top guest favourite
A cozy bedroom features a spacious bed covered with a striped blanket. A wicker chair is positioned nearby, and a bedside lamp provides soft lighting. Large windows offer views of colorful autumn trees, enhancing the serene atmosphere of the space.
Guest house in Rocheport
4.98 out of 5 average rating, 300 reviews

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.

Popular amenities for Wooldridge holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Cooper County
  5. Wooldridge