Family-friendly holiday rentals in Montgomery County

Historic Downtown cottage FULL of Amenities

Take a break and unwind at this peaceful guest cottage located on historic Greenwood Ave. 1 mile from downtown and APSU, this quaint home is full of amenities and waiting for you! Enjoy cooking in the equipped kitchen,dine in front of the electric fireplace with remote settings. Plenty of games and Roku TV to pass your time. The queen bedroom is ideal for 2 adults while the living room has 2 twin ottoman beds available for kids. Full bath, laundry room, and a desk for the working professional.

Paradise Hill Tiny House

Relax in this calm, stylish space. Come enjoy your stay at our small, quaint, inviting tiny house located in a peaceful country setting. Property is very close to the Historic Southside Market, Historic Collinsville and a short drive to beautiful Charlotte, TN where you can shop their unique variety of farm to table and craft stores. Only 14 miles to Clarksville, TN, 26 miles to Dickson, TN and 42 miles to Nashville! Come relax in the country and soak in the beauty and peacefulness of it all!

Home Theatre w/Warm Southern Comfort

2200 sq.ft home, comfortable, warmly decorated, open floor plan, 3bd, 2b w/ large porch, furnished upper deck with nightlights, no access from below for your safety and peace of mind. It overlooks a beautiful view of forrest greenery w/ local wild life. A pet enclosure; home theatre w/refreshments, foosball & lota of family games; Fire Pit- w/ wood; Laundry space; Deep freezer; Storage shed; Family walking track & park within 2 min walking. **(2) EXTERIOR CAMERAS FOR GUEST SAFETY

Entire 3BR House close to APSU Ft Campbell &Casino

Entire 3 bedroom house , located just minutes from Austin Peay, Fort Campbell, and the Oak Grove Casino. This home has a beautiful open floor plan with a kitchen, dining area, and living room for everyone to enjoy together. Go out into the spacious backyard which also includes a swing set for the kids! Enjoy this beautiful home and all that it has to offer. ✔3 Comfy Bedrooms ✔Fully Equipped Kitchen ✔Large Backyard ✔Smart TV ✔Washer/Dryer ✔High-Speed Wi-Fi ✔1 car garage & driveway

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

Tiny Town's Tiny Ship

Our tiny ship is a tiny house with a flair for the nautical. Our Tiny Ship is stranded between a few homes and tucked away from sight. She has everything you need as you visit our fair city,. We have a wet bathroom with a 6 gal hot water tank (10 min continuous hot water. And a map to help ye on your travels! ⚓️⚓️ We welcome one pet, but they must be crated when left alone, and a $15 pet fee. Also, it is located on a main road with neighbors, so complete silence is impossible.

Henrietta House: Quiet Comfort with Fenced Yard

Henrietta House is a recently renovated home on a quiet, leafy street in an established neighborhood. Perfect for families or anyone looking for a fun and relaxing getaway, the home has a full kitchen and a fenced back yard. We are a 15 minute drive to APSU and downtown Clarksville; 5 minutes from Exit 11 on I-24, 5 minutes to Publix and Walmart, 30-40 minutes to Ft. Campbell, 45 minutes to downtown Nashville. Driveway or garage parking. Dogs welcome. No added-on cleaning fee.

Tiny Barn on a Farm Hot Tub 45 min to Nashville

Remodeled June 2025, This a boutique style personalized romantic stay you won't find anywhere in Clarksville! Our Tiny BARN offers a romantic vibe with a private patio. The patio space is relaxing with a Hot Tub !! We have chickens, cows, a sweet pot belly pig, etc. We also grow. Only a half mile to some of our areas best local BBQ at Red Top. If you like Whiskey start at MB Rolland and try the Pink Lemonade then pop on over to Beachhaven 🍷 Winery.

Industrial Loft Downtown near the Cumberland River

LOCATION!!! Nestled in the heart of beautiful Historic Emerald district downtown Clarksville. This newly renovated loft is three blocks from F&M Bank Arena, River Walk, across the street from APSU, and minutes to Clarksville’s finest restaurants, bars, coffee shops, boutiques, museums, and art galleries! Walk or ride the provided Bicycles around the scenic downtown area! Less than 15 miles to Fort Campbell and just 45 miles to downtown Nashville!

Beautiful Home short walk to Downtown Clarksville!

Dine in this beautiful dinning area or coffee on your own private deck. This classy town home boasts open-plan living, with luxury style and stunning artwork. The combination of metals, velvet and wood in the interior make this a beautiful contemporary dream. 5 minute walk to downtown Clarksville. 45 minutes to Nashville. 20 minutes to Fort Campbell. Check out our other available listings within walking distance by clicking on our host profile.

Spacious | 4BR Boho | Family + Pet Friendly

Bring the whole family to this great place with lots of room for fun. This stylish 4 bedroom / 2.5 bath home is located in the Liberty Park neighborhod of Woodlawn. Just a few miles from Fort Campbell (Gate 10). This quiet, family-oriented community is conveniently close to both Clarksville and nearby recreational hot spots. The home is a full time Air-Bnb that is professionally cleaned and stocked with kitchen and bath essentials.

Stunning 5 Bed 2.5 Bath

Beautifully renovated 5 bedroom 2.5 bathroom home located in the heart of Clarksville! Close to all of the amenities of Fort Campbell Blvd, Wilma Rudolph Blvd, and Tiny Town Rd. Easily could sleep 10 or more! This home is pet friendly, with stylish furnishings and super comfortable beds. Serene patio space with market lights that backs to trees. Air hockey and foosball table in the garage for your enjoyment!.