Pet-friendly holiday rentals in Warren County

1888 Schoolhouse in Wine Country

Right in the middle of Missouri's wine country, this fully renovated 1888 Schoolhouse lets you explore wineries in the area or just sit on the front porch and wave at the locals. Perfect for two or use the fold out couch for additional guests. Pinckney, Missouri was the county seat of Warren County. Danial Boone once sat on the porch of the County Judge right across the street. This quiet street was once the hub of activity due to the Missouri River, now it is a quiet retreat from the noise.

Squirrel Run at Innsbrook Resort

WINTER ---> NOV-MAR: 4 -wheel drive car is recommended. In heavy snow, the cabin is deep in the woods & services would not be able to plow you out immediately. NO PARTIES. We have a 8 person occupancy. This includes holidays. Squirrel Run is nestled on 3 acres in a secluded wooded setting within the Innsbrook Resort Community. This 2-bedroom, 1-bathroom home sleeps 8 and offers everything from hiking, canoeing, swimming, or lounging around the firepit. More details on IG @squirrel_run_ibk

Vitality Retreat 1 block from DT/Riverfront/Shops

Gather & make memories at the Vitality Retreat! Located a block from historic downtown Washington restaurants/shops/bars, you will have ample amenities for a fun and rejuvenating stay. Pet friendly/fenced yard! Enjoy coffee in the gazebo, yard games, or 1-block walk to the riverfront! 15 minutes to wineries, 45 minutes from STL. Location perfect for memory making. 4 BRs, 4 Bathrooms ensure ample space! Pet friendly, please note any pets beyond 2 will be an additional $100 per pet. Thank you!!

Lakefront w/ Canoes, Fire pit, Ping Pong, Fishing

Come stay at "Redbird Cabin" our lakefront 3 bedroom A-frame home right on the water with beautiful lake views from the family room. We have plenty of space for families and friends with everything you need to enjoy your retreat. Our massive outdoor area makes for a great space to BBQ, relax, and sit by the fire pit. Located in a gated community within Innsbrook resort (an hour from STL), you'll love the community seasonal pool, restaurant, golf course, gym, playground, and hiking trails!

Updated 4b/3b+loft Chalet, on lake w/hottub

Escape to a secluded lakeside retreat, perfect for gatherings of up to 18 guests! The open-concept kitchen is designed for groups, while updated bathrooms add a touch of luxury. Tucked at the end of a quiet road and surrounded by woods, this chalet offers direct lake access and is close to Lake Aspen and the golf course. Relax in the spacious living areas or outdoors by the fire pit under the stars. Whether for adventure or relaxation, Hideaway Chalet is ideal for your next getaway!

Private 77 Acre Farm Hermann MO - Sleeps 8+

Secluded country escape with an elegant touch! Located just minutes from downtown Hermann, MO. This 3 Bedroom - 2 Full Bath sleeps 7 comfortably, but feel free to bring air mattresses. We will accommodate up to 10 without additional charges. From the moment you step foot on the property you can feel the relaxation. Fully stocked kitchen & gas grill to cook up whatever your heart desires. Relax by the fire pit. It’s just the perfect weekend get-a-way from the city.

*Historical* Aletha-Marie Krog Guest House

Built in 1895, this charming two story historic brick home is located in beautiful downtown Washington, Missouri. Just blocks away from bars, restaurants, art galleries and shopping. Guests will feel right at home with our 3 cozy bedrooms and 2 full bathrooms, a full eat-in kitchen, living room, and four season room. It's been said, many times, that there is a pleasant vibe or feeling to this beautiful old place. It's been around a long time.

Seclusion at its finest on 90+ Acres!

Settled in the middle of 90+ acres this property will bring you a peaceful secluded setting during your stay. These are adults only, however pets welcome! You will find yourself in the middle of no where with everything you need/want within 15-20 min. Personal patio with hot tub, full kitchen, indoor fireplace, and private setting. Open meadow with surroundings of trees with wildlife adds to this peaceful venue.

Relaxing Lakefront Chalet in Innsbrook Resort

Situated in the woods overlooking Foxfire Lake, this A-frame chalet provides gorgeous views throughout the year. Whether enjoying your morning coffee on the back deck, dropping a line in the lake from the dock, or cozying up with a good book in front of the fireplace, this chalet is sure to help you and your family find joy and relaxation.