Discover Your Perfect Wooldridge Vacation Homes

Best Vacation Homes in Wooldridge

Apartment
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like-icon10.0
Exceptional
(121 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£189/Night 7 Nights - £1,326
House
Map-icon
like-icon1.0
Average
(1 Review)
3 Bedrooms 2 Baths 9 Guests
  • Pet Friendly
    Pet Friendly
  • Child Friendly
    Child Friendly
£170/Night 7 Nights - £1,189
Apartment
Map-icon
like-icon10.0
Exceptional
(15 Reviews)
2 Bedrooms 1 Bath 4 Guests 1098 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£168/Night 7 Nights - £1,179
House
Map-icon
like-icon10.0
Exceptional
(68 Reviews)
1 Bedroom 1 Bath 6 Guests 832 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£108/Night 7 Nights - £754
star-icons-4
House
Map-icon
3 Bedrooms 2 Baths 8 Guests 1453.13 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
£353/Night 7 Nights - £2,468
Condo
Map-icon
like-icon10.0
Exceptional
(51 Reviews)
2 Bedrooms 2 Baths 8 Guests 1090 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£185/Night 7 Nights - £1,298
Apartment
Map-icon
like-icon10.0
Exceptional
(21 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£104/Night 7 Nights - £726
Cabin
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£89/Night 7 Nights - £622

Wooldridge Luxury Rentals

House
Map-icon
like-icon10.0
Exceptional
(17 Reviews)
7 Bedrooms 3 Baths 12 Guests 3500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£841/Night 7 Nights - £5,888
House
Map-icon
like-icon10.0
Exceptional
(35 Reviews)
4 Bedrooms 3 Baths 10 Guests 3600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£839/Night 7 Nights - £5,872
House
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Hot Tub
    Hot Tub
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£767/Night 7 Nights - £5,366
House
Map-icon
1 Bedroom 2 Baths 6 Guests 1711.46 ft²
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
£720/Night 7 Nights - £5,038
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
4 Bedrooms 3 Baths 10 Guests 3000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£656/Night 7 Nights - £4,596
Hotel
Map-icon
3 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£598/Night 7 Nights - £4,183
Hotel
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3 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£598/Night 7 Nights - £4,183
Hotel
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4 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£461/Night 7 Nights - £3,227

Wooldridge Pet Friendly Vacation Rentals

Condo
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like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 2 Baths 4 Guests 1470 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£238/Night 7 Nights - £1,668
star-icons-4
Apartment
Map-icon
4 Bedrooms 2 Baths 8 Guests 1797.57 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
£336/Night 7 Nights - £2,354
House
Map-icon
like-icon10.0
Exceptional
(16 Reviews)
3 Bedrooms 1 Bath 6 Guests 1346 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£163/Night 7 Nights - £1,143
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 3 Baths 6 Guests 1550 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£205/Night 7 Nights - £1,435
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House
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1 Bedroom 2 Baths 4 Guests 2777.09 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
£161/Night 7 Nights - £1,126
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 456 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£46/Night 7 Nights - £326
Apartment
Map-icon
like-icon8.0
Excellent
(1 Review)
1 Bedroom 1 Bath 2 Guests 456 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£47/Night 7 Nights - £331
New
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 456 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£52/Night 7 Nights - £362

Wooldridge Large Vacation Homes

Apartment
Map-icon
like-icon10.0
Exceptional
(90 Reviews)
3 Bedrooms 2 Baths 10 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
£394/Night 7 Nights - £2,759
House
Map-icon
like-icon9.8
Exceptional
(58 Reviews)
3 Bedrooms 2 Baths 10 Guests 1260 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£207/Night 7 Nights - £1,448
House
Map-icon
like-icon9.4
Exceptional
(28 Reviews)
4 Bedrooms 2 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£113/Night 7 Nights - £789
House
Map-icon
like-icon8.6
Fabulous
(34 Reviews)
4 Bedrooms 2 Baths 12 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£129/Night 7 Nights - £902
New
House
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£200/Night 7 Nights - £1,402
Cottage
Map-icon
like-icon9.8
Exceptional
(19 Reviews)
4 Bedrooms 1 Bath 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£202/Night 7 Nights - £1,413
House
Map-icon
like-icon10.0
Exceptional
(116 Reviews)
5 Bedrooms 3 Baths 16 Guests 3600 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£586/Night 7 Nights - £4,099
star-icons-3
Apartment
Map-icon
like-icon10.0
Exceptional
(22 Reviews)
4 Bedrooms 2 Baths 12 Guests 1450 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
£240/Night 7 Nights - £1,679

Why Choose Rent By Owner for your Wooldridge Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Wooldridge

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as seasonal weather patterns and local events in this region often influence the best period for booking your ideal vacation rentals.

Peak Season Highlights

spring
Spring (March to May)

Experience the region's lush landscapes and blooming flora, making this a popular time for outdoor activities and scenic drives in Wooldridge.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Enjoy the vibrant fall foliage and cooler temperatures that create an ideal setting for exploring the area's natural beauty.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June to August)

While summer offers longer daylight hours, the heat can be quite warm, making it less busy for those seeking a quieter retreat nearby.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
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Winter (December to February)

During this period, colder weather might limit outdoor activities, but it’s still a peaceful time to enjoy cozy accommodations in this destination.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Wooldridge

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy grilling and outdoor dining on the spacious porch or patio, perfect for relaxing in this scenic area.
  • Take advantage of private outdoor spaces such as yards or gardens to unwind amidst nature.
  • Make use of outdoor fire pits to gather around and share stories during cool evenings here.
  • Explore nearby hiking or walking trails that often accompany vacation rentals in this region.
  • Benefit from access to swimming pools or private ponds available at select properties in the area.
  • Utilize outdoor recreational equipment like kayaks, paddleboards, or bikes often found with rental listings here.
  • Relax under shaded areas or umbrellas that provide comfort while enjoying the regional outdoor scenery.
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Family Activities

  • Wooldridge Water Park: Enjoy a day of splashing and relaxation at the local water park, perfect for family fun in this charming area.
  • Wooldridge Nature Trails: Explore scenic trails that offer opportunities for hiking and wildlife observation, ideal for outdoor adventures with children.
  • Local Fishing Spots: Spend quality time together by fishing in nearby lakes and rivers, a peaceful activity for families visiting the region.
  • Community Events and Festivals: Participate in seasonal festivals and community gatherings that showcase local culture and provide entertainment for all ages.
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Adult Activities

  • Missouri River Excursions: Embark on scenic boat trips along the Missouri River, offering a tranquil escape and stunning views in this region.
  • Local Wildlife Watching: Enjoy peaceful mornings observing native wildlife at nearby nature reserves or wetlands that add to the area's natural charm.
  • Fishing Experiences: Take advantage of abundant fishing opportunities in the area’s lakes and rivers, perfect for relaxing afternoons by the water.
  • Hiking and Nature Trails: Discover well-maintained trails that wind through the picturesque landscape, ideal for outdoor enthusiasts seeking serenity and adventure.

Wooldridge Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Research the local area to identify nearby attractions and activities that can enhance your stay in this charming Missouri destination.
  • Choose the Right Property: Select a well-reviewed vacation rental that offers the comfort and amenities you need for a relaxing experience here.
  • Explore Local Wildlife and Nature: Take advantage of outdoor opportunities within the region to enjoy the scenic beauty and natural landscapes surrounding your accommodation.
  • Communicate with Hosts: Reach out to your hosts beforehand to get personalized recommendations and insider tips for making the most of your time here.

Transportation Options

  • Personal Vehicles: Renting or bringing your own car offers the most flexibility for exploring this region comfortably at your own pace.
  • Local Taxi Services: Reliable taxi options are available here, providing convenient transportation to nearby attractions and amenities within the area.
  • Public Transit: Buses serve the region, offering an affordable way to get around without the hassle of parking or driving yourself.
  • Car Rentals at Nearby Airports: Accessible car rental agencies near regional airports make it easy to pick up a vehicle upon arrival and start your adventure in the area immediately.

Local Customs Options

  • Community Gatherings: Participating in local events and festivals is a cherished tradition that brings residents together in this region.
  • Respect for Nature: Believing in the importance of preserving the area's natural beauty, locals often engage in outdoor activities with environmental mindfulness.
  • Regional Cuisine: Enjoying traditional dishes at neighborhood eateries offers a glimpse into the area's rich culinary heritage.
  • Historic Appreciation: Visitors are encouraged to learn about longstanding customs that highlight the region's historical significance.

Frequently Asked Questions About Wooldridge?

2. How many vacation rentals have private pools in Wooldridge?

There are 5 vacation rentals with private pools near Wooldridge. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Wooldridge are best for families?

If you are looking for a family-friendly vacation home in Wooldridge, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wooldridge:

4. How many Rentbyowner vacation rentals are available in Wooldridge?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 258 in the Wooldridge area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Wooldridge. 

5. What is the cancellation policy for vacation rentals in Wooldridge, Missouri?

Cancellation policies vary by property owner, so it’s important to review the specific listing details on the booking site. You can usually find this information in the rental terms or contact the host directly for clarification.

6. How do I secure my booking in Wooldridge's vacation rentals?

Bookings are secured once you complete the reservation process and any required payments are processed. Be sure to review the booking instructions and confirm your reservation through the platform to ensure your stay is guaranteed.

7. Are there any additional fees associated with staying at a vacation rental here?

Additional fees such as cleaning, service charges, or taxes may apply based on the property and local regulations. These details are typically listed during the booking process, so review the total cost before confirming your reservation.

8. What amenities are commonly available in vacation rentals in this area?

Most vacation rentals in this region include amenities such as Wi-Fi, parking, and complete kitchen facilities. For specific features, refer to the individual property listing or contact the host directly.

9. What should I know about check-in and check-out procedures during my stay?

Check-in and check-out times are established by each property owner and are outlined in the listing. If you have special requirements or questions, it's best to communicate directly with the host ahead of your arrival to ensure a smooth experience.

Wooldridge Top Rated Vacation Rentals

Hotel
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£199/Night 7 Nights - £1,396
Hotel
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£214/Night 7 Nights - £1,496
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£108/Night 7 Nights - £759
Hotel
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Baths
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£427/Night 7 Nights - £2,986
Hotel
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£199/Night 7 Nights - £1,396
Hotel
Map-icon
like-icon9.6
Exceptional
(9 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£106/Night 7 Nights - £746
star-icons-3
Hotel
Map-icon
like-icon9.4
Exceptional
(1001 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
£138/Night 7 Nights - £968
Hotel
Map-icon
like-icon9.2
Exceptional
(10 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£106/Night 7 Nights - £746