Smoking friendly vacation rentals in Montgomery County

4.97 out of 5 average rating, 62 reviews

Two vibrant blue kayaks are positioned on a manicured green lawn, overlooking the tranquil waters of Lake Conroe. A dock is visible in the background, with boats moored, and a serene sky enhances the waterfront setting.

Home in Willis

Waterfront getaway w/boat dock, kayaks & games

Relax with the whole family at this fully updated waterfront home. A true hidden gem on the water with plenty of outdoor space and your own boat slip. Large screened patio, kayaks, and fishing. Bring your boat or just yourselves and indulge in a stylishly furnished home equipped with everything a home away from home provides. Enjoy watching the sunset while sipping your favorite drink, BBQing in the backyard, or whatever floats your boat. Need more space? Check out our sister listing next door.

4.87 out of 5 average rating, 31 reviews

A well-maintained pool area is surrounded by lounge chairs and shaded umbrellas. Lush greenery lines the perimeter, providing a tranquil setting. The layout includes a small fire pit nearby and steps leading to the pool from the surrounding pathways.

Condo in Montgomery

Lake Conroe w/Pool/CanalViews & Boat launch access

Come stay and enjoy this beautiful condo on Lake Conroe w/full community access to pools, park, gym, golf course, a boat ramp, bar & grill and yacht club w/in walking distance. This home features: TV’s in living & bedroom spaces w/WI-FI. Don’t miss out on the cozy space w/your own private patio w/partial lake & full pool views located by some of Walden’s best amenities. This condominium comes fully stocked with all your day to day essentials including utensils, toiletries, bedding, and coffee

5 out of 5 average rating, 4 reviews

A covered patio area features a comfortable seating arrangement with two chairs and a small table. A grill can be seen to the left of the seating, surrounded by lush greenery and tall trees, while large glass doors lead into the living space.

Tiny home in Montgomery

Game Junction

Lake Roy's Game Junction is the ultimate hang out! This quaint accommodation is a sweet place to stay offering tons of fun w/ a pool table, shuffle board, a bowling game, etc. along with kitchenette, bathroom, sitting area, and two huge TVs. A queen bedroom, murphy bed sleeps 1-2, plus a sofa bed. Just outside your door, you can play sand volleyball, grill, and chill-lax by the fire pit. We just recently added a fenced area to the left of our structure. Not conducive for children under 15.

Camper/RV in Plantersville

A vintage camper is illuminated at night, showcasing its nostalgic exterior with soft lighting from inside. Windows are adorned with red curtains, and the surrounding area includes grass and subtle ground lighting, creating a welcoming ambiance.

5 out of 5 average rating, 3 reviews

Little Boy Blue - Renovated Vintage Camper

Country relaxing with shade! This renovated vintage camper is one of many glamping listings at our camp. It has a kitchen table that turns into a full bed and also a pull-out full couch, full bath with shower/sink/toilet, full kitchen, small stand-up charcoal grill, 4 chairs and a private fire ring. It is near our Courtyard area, with easy access to the cowboy pool for use. Tent campers or others in small campers may be in the vicinity. No Class A RV's or generators allowed in the camp.

4.85 out of 5 average rating, 54 reviews

A modern living area is showcased with a plush gray sofa and a stylish accent chair. Sliding glass doors open to a green view, while sheer white curtains allow natural light to filter in. A decorative area rug and wall art add a touch of comfort.

Condo in Montgomery

Cozy Walden 1st Flr Condo: Smoking, Pool/Jacuzzi!

Escape to a romantic retreat at Walden on Lake Conroe. This cozy ground-floor spot near Margaritaville features golf course views, pool/jacuzzi access, and a peaceful vibe. Perfect for couples, with an outdoor smoking area and endless golf for members—your serene getaway starts here. Enjoy nearby dining, lakefront strolls, and stunning sunsets from your patio. Whether it’s a weekend escape or a longer stay, this hideaway is designed for connection, relaxation, and unforgettable memories.

4.9 out of 5 average rating, 117 reviews

A rustic log cabin stands surrounded by greenery, featuring a wooden deck with seating. Two flags, representing the United States and Texas, gracefully flutter on either side of the entrance. The pathway leads to a spacious yard, inviting relaxation in the countryside.

Tiny home in Montgomery

@LogCabin_BnB Tiny Home Renaissance Festival

Come a stranger-leave a friend! Welcome to the bucolic countryside: enjoy bird-watching, outdoor fires, tree swings, horseshoe pit, yard Yahtzee, feed the ducks & geese, pick berries/flowers, have a yoga/meditation session on the workout platform, encounter the sounds and sights of coyotes, barred owls, horses, trains, donkeys, laughing children, or just the sound of your own heartbeat as you lay in the hammock outdoors. Come. Stay. Enjoy!! NO STOVE but toaster, micro, etc. included.

4.8 out of 5 average rating, 15 reviews

A charming exterior view of a white house featuring a sloped roof and arched windows. Lush green landscaping frames the front yard, complemented by a large tree and a well-maintained lawn. A spacious driveway leads to the entrance, providing an inviting first impression.

Home in Montgomery

4 Bedroom 3 Bath home in April Sound!

Relax with the whole family at this peaceful place to stay. Fabulous home with a study, formal dining room and huge living room with fireplace and built-ins. Gorgeous kitchen with lots of cabinets and plenty of room for the chef. Large master bedroom with master bath, separate shower and large walk in closet. Huge game room or 4th bedroom upstairs which has a full bath. Large fully fenced backyard with covered patio and firepit area. April sound is a gated neighborhood on lake Conroe.

4.85 out of 5 average rating, 34 reviews

An open dining area is highlighted by a large wooden table, surrounded by padded chairs. A forest-themed mural provides a calming backdrop, while dark gray curtains frame a window. A modern stainless steel refrigerator stands nearby, enhancing the kitchen's functionality.

Home in Montgomery

Lake House Get-A-Ray

Built by hand in 1962 & recently renovated, The Lake House has been a cozy place for family & friends to gather for decades. Now we'd like to share this special place with you! The screened porch allows a comfortable space to watch the morning come & the evening go. Just behind the house is a picturesque fishing pond & a short drive puts you at the Waterpoint Marina on Lake Conroe. Also offers RV hook ups for additional fee & plenty of space to park the boat w/lake access!

4.91 out of 5 average rating, 139 reviews

A tiny home is depicted with a blue exterior and white trim, featuring a welcoming front porch. Steps lead up to the entrance, framed by greenery and wildflowers in the foreground. Tall trees surround the property, enhancing its private setting.

Tiny home in Willis

Bluebonnet ~Quiet Retreat~ HotTub & Dog Friendly

The simplicity & relaxation of our premium 399 Sq. Ft. tiny home is so refreshing and unique. This home sleeps four. It has a Queen size bed and a luxury pullout Queen sofa. The fully equipped kitchen is perfect to fix up your gourmet meals. The Bluebonnet is nestled beside our sparkling 1/2 acre pond with a fountain, ducks and fish. A wooded area behind and open fields out front brings a nice breeze across the porch. Makes for a perfect place to enjoy the sunset or stars!

4.98 out of 5 average rating, 55 reviews

The exterior of a mid-century brick home is showcased, featuring a white picket fence surrounding a grassy yard. A front door with a decorative wreath is centered, flanked by windows with black shutters. Potted plants are seen at the base of the fence.

Home in Willis

Stay Awhile. Best extended stay.

Bring the whole family including the furry ones. Fully fenced front & back yard. Covered patio. King size bed, 65 inch TV in the primary bedroom. Walk in closet. Driveway can accommodate a boat/trailer 5 miles to Lake Conroe. Located in the heart of Willis. The Lonestar Convention Center and Expo is less than 10 miles away. Grill and covered patio with lots of seating. Play tether ball while the burgers grill. Discounts for longer stays starting with week one.

4.91 out of 5 average rating, 268 reviews

A charming cabin surrounded by lush greenery features a welcoming front porch with a wooden railing. Rocking chairs offer a comfortable spot for relaxation. The entrance is highlighted by warm tones and natural textures, creating a cozy and inviting appearance.

Cabin in Magnolia

Cloud's Cabin-Cozy Cabin Combo in the Piney Woods

Welcome to Cloud's Cabin! We are located an easy drive northwest of Houston. Cloud's Cabin is nestled in the piney woods of Magnolia, Texas and offers a cozy little spot for the perfect getaway. Whether it's a day or a week, Cloud's Cabin is a quiet, private spot to rest up. We are situated on a small self-sufficient working homestead. We grow seasonal vegetables and exotic rare fig tree varieties from around the world! We are big FIG enthusiast here!