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!!

Sweet Cherry Escape | JZ Vacation Rentals

Step into a cozy, inviting living room adorned with soothing blue and cream hues. Sink into the plush furnishings and enjoy your favorite show on HDTV or opt for board games. The remodeled kitchen boasts stainless steel appliances, a butcher block counter, and ample space for cooking. Coffee lovers will find both a single-cup maker and a full pot. The generous dining area accommodates the whole group. Stay productive at the dedicated workspace. See what adventures await at The Cherry House!

Seclusion at its finest on 90+ Acres!

Tucked away on 90 acres of private land, this cabin offers the perfect blend of peaceful seclusion and modern comfort. Surrounded by open meadows and wooded landscapes, it’s a serene retreat where wildlife and quiet moments come naturally. However, shops and essentials are just 15–20 minutes away. With a private patio hot tub, fully equipped kitchen, and a cozy indoor fireplace a comfortable stay is ensured. This is an adults-only property. Pets are welcome. Two guest maximum. No hunting.

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!

Verein Heritage Loft

Verein Heritage Loft, located in the heart of historic downtown Washington's arts and entertainment district, serves as a stylish retreat from everyday life. The recent restoration of this iconic 1855 building, rich with German heritage, offers unmatched comfort and convenience. Enjoy riverfront views, scenic walking trails (Katy Trail), quaint boutique shopping, bar hopping, all within a lively family entertainment district. Visit by Amtrak while enjoying our beautiful wine country!

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.

Cozy 1882 Farmhouse-10 minutes from Wine Country

Getaway to The Farmhouse located in the quiet country near Hermann, Berger and New Haven. Gather with friends and family where children will enjoy space to run/play in and gathering for s'mores around an evening fire. The area boasts of wineries with weekends of fun themed festivities. Set rate on first two guests $145/night (smart pricing in effect on event weekends) . $55 each additional guest/night. Infant- 2 yrs. free, 3-12 $30/night Pets: $30 each pet/one time charge

*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.

Fenced Yard-near riverfront, wineries, PurinaFarms

Soak in the charm of this cozy brick charmer in downtown WashMO! The home is updated and ready for you to unwind and relax. It's just a few minutes from the riverfront, walking distance to all downtown shops & restaurants, and a short drive to Augusta wine country or Purina Farms. Bring your family & friends and enjoy beautiful Washington at the Rand house!

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.