Holiday rentals in Wooldridge

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Top-rated holiday rentals in Wooldridge

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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, 282 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, 189 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.

Guest favourite
A cozy bedroom area is equipped with a queen size bed adorned with decorative pillows. Two bedside lamps illuminate the space, complemented by a small chair nearby. Windows with sheer coverings provide natural light, while a plant adds a touch of greenery to the room.
Flat in Boonville
4.86 out of 5 average rating, 303 reviews

Santa Fe Hideaway

Santa Fe Hideaway Airbnb Basement apartment conveniently located off of I-70 on the historical Santa Fe Trail in Boonville Missouri. Safe driveway parking with security cameras well-lit for late night arrivals. 500 ft. from the Katy Trail, great for hiking and biking enthusiast. 3 min walk to the Isle of Capri Casino, scenic river views close by. Close to downtown and the Missouri Soccer Park . Private keyless entry, master bedroom, full bath, living area and breakfast nook. High speed Wi-Fi.

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, 558 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, 147 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 spacious living area features a comfortable sofa adorned with colorful cushions. A stylish orange and white area rug anchors the space, and a wall-mounted television is positioned within view. Artistic decor and a side table enhance the inviting environment.
Flat in Columbia
4.98 out of 5 average rating, 480 reviews

Ivy Cottage Off Broadway

Hidden gem in ❤️ of Columbia. Designed and built specifically as a STR. Minutes from Highway 70, downtown, and MU. Charming, completely separate apartment above the main residence with private outdoor courtyard. Open floor plan includes master bedroom, separate from living space. Sofa bed in living room. Beautifully appointed and furnished. Includes new Tempur-pedic mattress, bar, coffee station, functional kitchen, keypad entrance. Parking in driveway for ONE car, quiet, and cozy.

Guest favourite
An oversized porch features wooden flooring and a table surrounded by striped chairs. Potted plants with flowers add color, while a small fireplace sits adjacent. Wooden pillars support the roof, and trees are visible in the background, creating a serene outdoor space.
Home in Rocheport
4.98 out of 5 average rating, 339 reviews

Rocheport Blufftop Bungalow * walk to trail*

Welcome to the bungalow on the hill in historic Rocheport w/ 3 BR, 2.5 baths, oversized porch, game room, garage, electric fireplace all within walking distance to MKT trail & downtown shops, restaurants & galleries or less than a mile to local award- winning winery. All yours to enjoy with antique furnishings, beautiful lighting & a short drive to Columbia. As nearby residents we're excited for you to experience why Rocheport was voted Best Tiny Town in MO by Southern Living mag!

Top guest favourite
The exterior of the Grain Bin Cabin is showcased beside a tranquil pond, reflecting the cabin's metallic structure. Adirondack chairs surround a firepit on the grass, with picnic tables positioned nearby, creating an inviting outdoor space.
Cabin in Versailles
4.99 out of 5 average rating, 137 reviews

Beautiful Grain Bin Cabin, Highland Cows, firepit

Welcome to our charming boho-inspired Grain Bin Cabin, the Highland is ideal for 2-3 adults or 2 adults and 2 smaller children. Upstairs, you'll find a comfortable king bed in the loft, while downstairs features a cozy futon in the main living space. The full kitchen is equipped with everything you need. Full Bath with a walk-in shower downstairs. Experience a serene countryside getaway with breathtaking sunsets and peaceful surroundings, just moments away from Versailles.

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, 808 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 & wildlife preserve then, we are not the right fit for each other. We request you respect our philosophy & cherished space.

Guest favourite
A living area features a red leather sofa and a black accent chair, with a coffee table placed in front. A dining area with a small table and chairs is visible. A large TV mounted on the wall displays content, while natural light enters through window treatments.
Flat in Columbia
4.94 out of 5 average rating, 182 reviews

2 Bed 1 Bath Southside Columbia 7 min to Mizzou

Freshly remodeled pet friendly(with $75 pet fee per stay)2 bedroom 1 bath duplex located 7 min from Mizzou campus, major hospitals and 9 min drive downtown. Includes Wi-Fi, desk, in unit washer/dryer. Grocery, convenience stores, restaurants and bar located close by. Apartment has all necessities provided including stocked kitchen. 42 inch smart TVs in bedrooms and 65 inch smart tv in living . Walkout basement is unfinished and and only to be used to access laundry

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, 107 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.

Top guest favourite
The exterior of a tiny home with a modern farmhouse design is presented, featuring a red metal roof and brown metal siding. A cozy porch area is furnished with seating, and a colorful quilt square is displayed on the wall, adding a decorative touch.
Tiny home in Fulton
4.99 out of 5 average rating, 215 reviews

Charming tiny home - Nova’s House

Reconnect with nature at this tiny home on a working horse facility. Enjoy sitting outside on the patio, starting a fire in the fire pit, or watching deer and turkey wander by. If you are so inclined to interact with horses, we offer both riding and ground lessons for beginners to advanced - Maplewood Farm has been in business for almost 30 years! Located just 5 miles from Fulton, MO and only 20 miles from Columbia, MO and easy access to I70 and Hwy 54

Popular amenities for Wooldridge holiday rentals

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