Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Cottage in Edwards

4.85 out of 5 average rating, 20 reviews

Horse Shoe Hideaway

NateRating, 5 stars1 month ago

This was a great cabin. It was clean and quiet in March. We enjoyed the pellet grill and the patio. Be aware they let the water out of the lake in March and the boat ramp and dock are unusable. Brown Bend access (30 min) is the closes boat launch we found. Overall, a great stay!

Superhost

Home in Gravois Mills

4.95 out of 5 average rating, 20 reviews

Private Dock & Hot Tub Retreat

NoraRating, 5 stars1 month ago

Beautiful home with your OWN dock! We loved being able to sit in the hot tub and look at the lake. The house was clean and felt very safe. Our favorite place to eat nearby was Little Basshole’s! The bar had super friendly staff and good, classic American food. We grabbed some take out and had a few drinks by the lake. It was glorious! Having been at many lake houses, it was not too shocking to see large loose gravel around the lake but please note that before traveling. We ended up arriving during a torrential downpour and I was very thankful to have my all-wheel drive vehicle. Overall, it was an awesome experience and we hope to be back.

Top Guest favourite

Home in Gravois Mills

4.97 out of 5 average rating, 149 reviews

*Wow, Luxury 5BR, 4BA Edgewater Escape w/ Hot Tub!

KristenRating, 5 stars1 month ago

⭐️⭐️⭐️⭐️⭐️ Title: A Wonderful Experience for Our Group! ⭐️⭐️⭐️⭐️⭐️ As the organizer of our trip, I couldn’t have asked for a better experience at this Airbnb! The property offered multiple relaxing areas where everyone could unwind, making it easy to cater to different preferences. I loved that we could enjoy quiet moments on the porch while still being close to town for fun outings. Brady was incredibly helpful, providing great recommendations and ensuring we had everything we needed for a smooth stay. Our group left feeling refreshed and happy, and I can’t wait to plan another getaway here! Highly recommend for anyone looking to gather friends or family!

Superhost

Home in Sunrise Beach

4.83 out of 5 average rating, 125 reviews

Awesome Ozark Lakefront View!!!

RubyRating, 5 stars5 months ago

This was exactly what my family and I were looking for! The view was breathtaking, and it was a much needed break from life in the city. Jason provided very clear instructions, and it made our check-in very smooth (which was so helpful after 9 hours on the road, and it being so late when we arrived). The kids loved the room with the bunk beds, and the outdoor patio was beautiful. Everyone had a great time, and my kids already asked to go back during the summer time. Luckily, the weather was kind to us and we were able to spend so much time outdoors. Thank you, Jason! :)

Superhost

Home in Lake Ozark

5 out of 5 average rating, 3 reviews

Waterfront Paradise/HotTub/Boat&JetSki Options

ChristianRating, 5 stars3 weeks ago

We loved our stay! It was perfect for a weekend getaway. The hot tub ended up being the center of attention with the rainy/cold weather we experienced while there. Their recommendations book is filled with tons to do and great food recommendations. We will be staying again!

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Popular amenities for Windsor holiday rentals

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Other great holiday rentals in Windsor

Superhost

Home in Osage Beach

4.67 out of 5 average rating, 64 reviews

Spacious | Family Friendly | Tan-Tar-A Estates

AlishaRating, 5 stars5 months ago

The house was absolutely perfect for our family to all get together for Thanksgiving. There were only a couple issues while we were there but the host addressed them immediately so I feel no need to write them here. The house was clean. The location is great. We would DEFINITELY rent this house again for another holiday get-together in the future.

Top Guest favourite

Apartment in Lake Ozark

4.99 out of 5 average rating, 121 reviews

Lovely 1-bedroom lakeview rental with patio

CherishRating, 5 stars3 weeks ago

Great stay. As described!

Superhost

Home in Osage Beach

5 out of 5 average rating, 11 reviews

Margaritaville- 6 bed/7 bath home! 5000 sq.ft!

NoahRating, 5 stars6 months ago

The house was beautiful and exactly as advertised. Thank you Denise!

Superhost

Home in Edwards

5 out of 5 average rating, 8 reviews

Rustic Hideaway

SeanRating, 5 stars6 months ago

Great place! Will stay again if back in the area!

Top Guest favourite

Condo in Camdenton

5 out of 5 average rating, 8 reviews

Wheat’s no wake zone

DorisRating, 5 stars1 week ago

Sarah was an awesome host! The space was immaculate but very cozy. It was a perfect set-up for our stay as we were on a stop-over for a business meeting. It is a top floor condo so there are stairs, which was totally fine for us because it gave us the prettiest views of the lake! A place I would for sure stay at again if in the area.

Superhost

Home in Osage Township

4.67 out of 5 average rating, 3 reviews

Cozy home on Par 4 with golf cart and fireplace

AlexandraRating, 5 stars5 days ago

Tara was a great host and the place was amazing! It was within walking distance of a great trail, very close to the water and had a golf cart to take to the resort just down the road! She was quick to respond with everything we needed and flexible with checkout which was amazing! The best part, when we arrived, there was the cutest little dog bed and dog food/water bowls for our puppy!!

Superhost

Home in Osage Beach

4.89 out of 5 average rating, 9 reviews

Captain’s Cove at Margaritaville-Lakefront/Hot Tub

DenishaRating, 5 stars2 weeks ago

We just returned from a fantastic spring break at Kathleen's residence in Margaritaville! The space was perfect for our family of five and our beagle! The residence itself is beautifully appointed, offering plenty of space for our family. The open layout provided a perfect setting for family bonding, while the cozy bedrooms ensured everyone had a restful night’s sleep. We loved the fully equipped kitchen, which made preparing meals a breeze. The location is ideal, offering beautiful views of the Lake of the Ozarks. We enjoyed lounging in the private hot tub and exploring nearby attractions. Kathleen was an outstanding host, always available to help and provide local tips. Overall, we had an amazing time and created unforgettable memories. We highly recommend Kathleen's residence and can't wait to return!

Guest favourite